Isopropyl 2,5-anhydro-6-azido-3,6-dide­oxy-d-xylo-hexonate

Watkin, D.J.; Watterson, M.; Tranter, G.E.; Edwards, A.A.; Fleet, G.W.J.

doi:10.1107/S1600536805042133

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 62| Part 1| January 2006| Pages o363-o365

doi:10.1107/S1600536805042133

Isopropyl 2,5-anhydro-6-azido-3,6-dideoxy-D-xylo-hexonate

David J. Watkin,^a ^* Mark Watterson,^b George E. Tranter,^c Alison A. Edwards ^c and George W. J. Fleet ^b

^aDepartment of Chemical Crystallography, Chemical Research Laboratory, Mansfield Road, Oxford OX1 3TA, England, ^bDepartment of Organic Chemistry, Chemical Research Laboratory, Mansfield Road, Oxford OX1 3TA, England, and ^cBiological Chemistry, Division of Biomedical Sciences, Imperial College, London SW7 2AZ, England
^*Correspondence e-mail: david.watkin@chem.ox.ac.uk

(Received 14 December 2005; accepted 15 December 2005; online 23 December 2005)

Determination of the crystal structure of the title isopropyl azido ester, C₉H₁₅N₃O₄, confirmed its relative stereochemistry and validated further work on the use of a derived sugar amino acid (SAA) as a peptidomimetic.

Comment

Sugar amino acids (SAAs) are carbohydrates which contain amine and acid groups; SAAs have been the focus of much interest as dipeptide isosteres, foldamers and library scaffolds (Hill et al., 2001 ; Gruner et al., 2002 ; Schweizer, 2002 ; Chakraborty, Srinivasu, Tapadar & Mohan, 2004 ; Trabocchi et al., 2005 ). The preference for SAA oligomers (carbopeptoids) to adopt compact conformations as relatively short homooligomers will provide insight into the paradigm of protein folding. SAAs (2,5-O-cis configuration) structurally related to SAA (3) have a high propensity to adopt repeating β-turn conformations (Hungerford et al., 2000 ; Smith et al., 2003 ; Chakraborty, Srinivasu, Sakunthala et al., 2004 ). In contrast, some 2,5-O-trans SAAs have been shown to adopt helical conformations (Claridge et al., 1999 ; Claridge et al., 2005 ). The conformational complexity of these dipeptide isosteres is being further explored by preparation of structurally related analogues of the original SAA systems i.e. SAA (3) and corresponding diastereoisomers (Watterson et al., 2003 ).

The X-ray crystal structure (Fig. 1) firmly established the relative stereochemistry of the stereogenic centres in the title compound, (2). The absolute configuration of (2) (see scheme) is determined by the use of D-gulono-1,4-lactone as starting material.

The crystal packing consists of chains of molecules linked by hydrogen bonds and lying parallel to the a axis (Fig. 2). There are no unusual intermolecular contacts.

Figure 1
The title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

Figure 2
Projection of the title compound down the b axis, showing the hydrogen bonds (dashed lines) which link the molecules into columns.

Experimental

The title compound, (2), was prepared from the methyl azido ester (1) in good yield by transesterficiation in acidic propan-2-ol, as described by Watterson et al. (2003); subsequent deprotection by hydrolysis and hydrogenation afforded SAA (3). The sample of (2) was crystallized from diethyl ether–hexane.

Crystal data

C₉H₁₅N₃O₄
M_r = 229.24
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.4778 (7) Å
b = 11.0701 (13) Å
c = 18.2529 (15) Å
V = 1106.9 (2) Å³
Z = 4
D_x = 1.376 Mg m⁻³
Cu Kα radiation
Cell parameters from 22 reflections
θ = 21–44°
μ = 0.92 mm⁻¹
T = 190 K
Block, colourless
0.60 × 0.40 × 0.40 mm

Data collection

Enraf–Nonius Mach3 diffractometer
ω/2θ scans
Absorption correction: ψ scan(North et al., 1968 )T_min = 0.58, T_max = 0.69
1335 measured reflections
1335 independent reflections
1329 reflections with I > 2σ(I)
θ_max = 73.9°
h = 0 → 6
k = 0 → 13
l = 0 → 22
3 standard reflections frequency: 60 min intensity decay: 2.2%

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.104
S = 0.94
1335 reflections
146 parameters
H-atom parameters constrained
w = 1/[σ²(F²) + (0.07P)² + 0.57P], where P = [max(F_o²,0) + 2F_c²]/3
(Δ/σ)_max = 0.001
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Extinction correction: Larson (1970 ), Equation 22
Extinction coefficient: 159 (14)

Table 1
Selected geometric parameters (Å, °)

O1—C2	1.331 (3)
O1—C14	1.462 (3)
C2—O3	1.218 (3)
C2—C4	1.525 (3)
C4—O5	1.421 (3)
C4—C12	1.539 (3)
O5—C6	1.439 (3)
C6—C7	1.505 (3)
C6—C11	1.543 (3)
C7—N8	1.494 (3)
N8—N9	1.227 (3)
N9—N10	1.133 (3)
C11—C12	1.519 (3)
C11—O13	1.424 (3)
C14—C15	1.509 (3)
C14—C16	1.510 (4)

C2—O1—C14	116.44 (17)
O1—C2—O3	124.2 (2)
O1—C2—C4	111.63 (18)
O3—C2—C4	124.07 (19)
C2—C4—O5	109.68 (17)
C2—C4—C12	113.67 (18)
O5—C4—C12	104.84 (17)
C4—O5—C6	109.60 (16)
O5—C6—C7	111.26 (19)
O5—C6—C11	106.93 (16)
C7—C6—C11	112.91 (18)
C6—C7—N8	109.04 (19)
C7—N8—N9	113.4 (2)
N8—N9—N10	173.7 (3)
C6—C11—C12	102.52 (17)
C6—C11—O13	108.97 (17)
C12—C11—O13	110.87 (18)
C4—C12—C11	101.61 (18)
O1—C14—C15	106.30 (18)
O1—C14—C16	108.05 (19)
C15—C14—C16	113.3 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O13—H13⋯O3ⁱ	0.82	2.08	2.897 (2)	175
Symmetry code: (i) x+1, y, z.

Attempted refinement of the Flack (1983 ) parameter gave an inconclusive result, in the absence of Friedel pairs and the presence of only weak anomalous scattering effects. The absolute configuration was assigned from the known configuration of the starting material. The H atoms were all located in a difference map, but those attached to C atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H = 0.93–0.98 Å and O—H = 0.82 Å) and U_iso(H) values (in the range 1.2–1.5 times U_eq of the parent atom), after which they were refined with riding constraints.

Data collection: CAD-4 EXPRESS, (Straver, 1992 ); cell refinement: CAD-4 EXPRESS; data reduction: RC93 (Watkin et al., 1994 ); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: CAMERON (Watkin et al., 1996 ); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks global, 2. DOI: 10.1107/S1600536805042133/cf6481sup1.cif

Structure factors: contains datablock 2. DOI: 10.1107/S1600536805042133/cf64812sup2.hkl

Comment top

Sugar amino acids (SAAs) are carbohydrates which contain amine and acid groups; SAAs have been the focus of much interest as dipeptide isosteres, foldamers and library scaffolds (Hill et al., 2001; Gruner et al., 2002; Schweizer, 2002; Chakraborty, Srinivasu, Tapadar & Mohan, 2004; Trabocchi et al., 2005). The preference for SAA oligomers (carbopeptoids) to adopt compact conformations as relatively short homooligomers will provide insight into the paradigm of protein folding. SAAs (2,5-O-cis configuration) structurally related to SAA (3) have a high propensity to adopt repeating β-turn conformations (Hungerford et al., 2000; Smith et al., 2003; Chakraborty, Srinivasu, Sakunthala et al., 2004). In contrast, some 2,5-O-trans SAAs have been shown to adopt helical conformations (Claridge et al., 1999; Claridge et al., 2005). The conformational complexity of these dipeptide isosteres is being further explored by preparation of structurally related analogues of the original SAA systems i.e. SAA (3) and corresponding diastereoisomers (Watterson et al., 2003).

The X-ray crystal structure (Fig. 1) firmly established the relative stereochemistry of the stereogenic centres in (2). The absolute configuration of (2) (see scheme) is determined by the use of D-gulono-1,4-lactone.

The crystal packing consists of chains of molecules linked by hydrogen bonds and lying parallel to the a axis (Fig. 2). There are no unusual intermolecular contacts.

Experimental top

Computing details top

Data collection: CAD-4 EXPRESS, (Straver, 1992); cell refinement: CAD-4 EXPRESS; data reduction: RC93 (Watkin et al., 1994); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

Figures top

	Fig. 1. The title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.
	Fig. 2. Projection of the title compound down the b axis, showing the hydrogen bond (dashed line) which links the molecules into columns.

Isopropyl 2,5-anhydro-6-azido-3,6-dideoxy-D-xylo-hexonate top

Crystal data top

C₉H₁₅N₃O₄	D_x = 1.376 Mg m⁻³
M_r = 229.24	Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 22 reflections
a = 5.4778 (7) Å	θ = 21–44°
b = 11.0701 (13) Å	µ = 0.92 mm⁻¹
c = 18.2529 (15) Å	T = 190 K
V = 1106.9 (2) Å³	Block, colourless
Z = 4	0.60 × 0.40 × 0.40 mm
F(000) = 488

Data collection top

Enraf-Nonius Mach3 diffractometer	R_int = 0.000
Graphite monochromator	θ_max = 73.9°, θ_min = 4.7°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = 0→13
T_min = 0.58, T_max = 0.69	l = 0→22
1335 measured reflections	3 standard reflections every 60 min
1335 independent reflections	intensity decay: 2.2%
1329 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F²) + (0.07P)² + 0.57P], where P = [max(F_o²,0) + 2F_c²]/3
wR(F²) = 0.104	(Δ/σ)_max = 0.001
S = 0.94	Δρ_max = 0.25 e Å⁻³
1335 reflections	Δρ_min = −0.17 e Å⁻³
146 parameters	Extinction correction: Larson (1970), Equation 22
0 restraints	Extinction coefficient: 159 (14)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₉H₁₅N₃O₄	V = 1106.9 (2) Å³
M_r = 229.24	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 5.4778 (7) Å	µ = 0.92 mm⁻¹
b = 11.0701 (13) Å	T = 190 K
c = 18.2529 (15) Å	0.60 × 0.40 × 0.40 mm

Data collection top

Enraf-Nonius Mach3 diffractometer	1329 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.58, T_max = 0.69	3 standard reflections every 60 min
1335 measured reflections	intensity decay: 2.2%
1335 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 0.94	Δρ_max = 0.25 e Å⁻³
1335 reflections	Δρ_min = −0.17 e Å⁻³
146 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	1.0131 (3)	0.04582 (14)	0.13732 (8)	0.0286
C2	0.8763 (4)	0.07207 (19)	0.19548 (12)	0.0265
O3	0.7238 (3)	0.15214 (14)	0.19695 (9)	0.0327
C4	0.9240 (4)	−0.0150 (2)	0.25865 (11)	0.0260
O5	0.8152 (3)	0.03051 (14)	0.32375 (8)	0.0283
C6	0.9954 (4)	0.0942 (2)	0.36612 (11)	0.0265
C7	0.9236 (5)	0.2241 (2)	0.37739 (14)	0.0347
N8	0.7043 (4)	0.22905 (18)	0.42600 (11)	0.0370
N9	0.5797 (4)	0.31992 (19)	0.41699 (12)	0.0358
N10	0.4495 (5)	0.3992 (2)	0.41294 (17)	0.0538
C11	1.2409 (4)	0.0802 (2)	0.32561 (12)	0.0273
C12	1.1963 (4)	−0.0296 (2)	0.27753 (13)	0.0291
O13	1.2826 (3)	0.18508 (14)	0.28216 (9)	0.0319
C14	0.9818 (5)	0.1232 (2)	0.07308 (11)	0.0319
C15	1.0604 (6)	0.0491 (2)	0.00784 (12)	0.0430
C16	1.1340 (6)	0.2355 (2)	0.08420 (15)	0.0458
H41	0.8578	−0.0940	0.2460	0.0306*
H61	1.0054	0.0554	0.4140	0.0318*
H71	1.0540	0.2685	0.3992	0.0425*
H72	0.8814	0.2605	0.3297	0.0418*
H111	1.3776	0.0681	0.3590	0.0315*
H121	1.2259	−0.1050	0.3045	0.0333*
H122	1.2955	−0.0277	0.2341	0.0346*
H141	0.8056	0.1442	0.0675	0.0368*
H151	1.0365	0.0977	−0.0357	0.0639*
H152	1.2331	0.0309	0.0141	0.0642*
H153	0.9649	−0.0252	0.0055	0.0642*
H161	1.1211	0.2894	0.0430	0.0688*
H162	1.3011	0.2149	0.0890	0.0694*
H163	1.0845	0.2801	0.1274	0.0683*
H13	1.4026	0.1766	0.2560	0.0476*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0233 (8)	0.0367 (8)	0.0259 (7)	0.0027 (7)	0.0025 (7)	0.0002 (6)
C2	0.0200 (10)	0.0311 (10)	0.0285 (10)	−0.0031 (9)	0.0022 (9)	−0.0033 (8)
O3	0.0252 (8)	0.0400 (8)	0.0330 (8)	0.0063 (7)	0.0068 (7)	0.0024 (6)
C4	0.0210 (10)	0.0289 (10)	0.0279 (10)	−0.0023 (9)	0.0029 (8)	−0.0010 (8)
O5	0.0174 (7)	0.0401 (8)	0.0274 (7)	−0.0041 (7)	0.0043 (6)	−0.0021 (6)
C6	0.0200 (11)	0.0351 (11)	0.0242 (10)	−0.0004 (9)	0.0003 (9)	0.0020 (8)
C7	0.0251 (12)	0.0370 (11)	0.0421 (12)	−0.0031 (10)	0.0117 (11)	−0.0067 (10)
N8	0.0306 (10)	0.0408 (10)	0.0396 (10)	0.0029 (10)	0.0132 (9)	−0.0015 (9)
N9	0.0243 (10)	0.0402 (10)	0.0430 (10)	−0.0049 (10)	0.0035 (9)	−0.0087 (9)
N10	0.0306 (12)	0.0486 (13)	0.0823 (18)	0.0056 (12)	0.0026 (13)	−0.0082 (13)
C11	0.0155 (10)	0.0370 (11)	0.0295 (10)	0.0030 (9)	0.0008 (9)	0.0015 (9)
C12	0.0222 (11)	0.0335 (11)	0.0317 (10)	0.0053 (9)	0.0048 (9)	0.0039 (9)
O13	0.0225 (8)	0.0357 (8)	0.0375 (8)	−0.0018 (7)	0.0091 (7)	0.0008 (7)
C14	0.0299 (12)	0.0424 (12)	0.0235 (10)	0.0058 (11)	0.0024 (10)	0.0027 (9)
C15	0.0497 (16)	0.0508 (13)	0.0284 (11)	0.0106 (14)	0.0050 (12)	−0.0012 (10)
C16	0.0517 (17)	0.0447 (13)	0.0410 (12)	−0.0036 (14)	0.0114 (13)	0.0049 (11)

Geometric parameters (Å, º) top

O1—C2	1.331 (3)	C11—C12	1.519 (3)
O1—C14	1.462 (3)	C11—O13	1.424 (3)
C2—O3	1.218 (3)	C11—H111	0.974
C2—C4	1.525 (3)	C12—H121	0.983
C4—O5	1.421 (3)	C12—H122	0.962
C4—C12	1.539 (3)	O13—H13	0.817
C4—H41	0.975	C14—C15	1.509 (3)
O5—C6	1.439 (3)	C14—C16	1.510 (4)
C6—C7	1.505 (3)	C14—H141	0.998
C6—C11	1.543 (3)	C15—H151	0.969
C6—H61	0.976	C15—H152	0.974
C7—N8	1.494 (3)	C15—H153	0.976
C7—H71	0.954	C16—H161	0.962
C7—H72	0.986	C16—H162	0.947
N8—N9	1.227 (3)	C16—H163	0.968
N9—N10	1.133 (3)

C2—O1—C14	116.44 (17)	C6—C11—H111	112.6
O1—C2—O3	124.2 (2)	C12—C11—H111	112.0
O1—C2—C4	111.63 (18)	O13—C11—H111	109.7
O3—C2—C4	124.07 (19)	C4—C12—C11	101.61 (18)
C2—C4—O5	109.68 (17)	C4—C12—H121	111.2
C2—C4—C12	113.67 (18)	C11—C12—H121	111.4
O5—C4—C12	104.84 (17)	C4—C12—H122	111.1
C2—C4—H41	108.9	C11—C12—H122	111.6
O5—C4—H41	111.1	H121—C12—H122	109.7
C12—C4—H41	108.6	C11—O13—H13	111.1
C4—O5—C6	109.60 (16)	O1—C14—C15	106.30 (18)
O5—C6—C7	111.26 (19)	O1—C14—C16	108.05 (19)
O5—C6—C11	106.93 (16)	C15—C14—C16	113.3 (2)
C7—C6—C11	112.91 (18)	O1—C14—H141	109.4
O5—C6—H61	107.7	C15—C14—H141	108.8
C7—C6—H61	108.2	C16—C14—H141	110.9
C11—C6—H61	109.7	C14—C15—H151	107.9
C6—C7—N8	109.04 (19)	C14—C15—H152	107.3
C6—C7—H71	110.7	H151—C15—H152	110.1
N8—C7—H71	109.6	C14—C15—H153	109.9
C6—C7—H72	109.3	H151—C15—H153	111.1
N8—C7—H72	108.7	H152—C15—H153	110.5
H71—C7—H72	109.5	C14—C16—H161	111.4
C7—N8—N9	113.4 (2)	C14—C16—H162	110.4
N8—N9—N10	173.7 (3)	H161—C16—H162	107.0
C6—C11—C12	102.52 (17)	C14—C16—H163	112.0
C6—C11—O13	108.97 (17)	H161—C16—H163	107.4
C12—C11—O13	110.87 (18)	H162—C16—H163	108.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O3ⁱ	0.82	2.08	2.897 (2)	175

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₉H₁₅N₃O₄
M_r	229.24
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	190
a, b, c (Å)	5.4778 (7), 11.0701 (13), 18.2529 (15)
V (Å³)	1106.9 (2)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.92
Crystal size (mm)	0.60 × 0.40 × 0.40

Data collection
Diffractometer	Enraf-Nonius Mach3 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.58, 0.69
No. of measured, independent and observed [I > 2σ(I)] reflections	1335, 1335, 1329
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.104, 0.94
No. of reflections	1335
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.17

Computer programs: CAD-4 EXPRESS, (Straver, 1992), CAD-4 EXPRESS, RC93 (Watkin et al., 1994), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996), CRYSTALS.

Selected geometric parameters (Å, º) top

O1—C2	1.331 (3)	C6—C11	1.543 (3)
O1—C14	1.462 (3)	C7—N8	1.494 (3)
C2—O3	1.218 (3)	N8—N9	1.227 (3)
C2—C4	1.525 (3)	N9—N10	1.133 (3)
C4—O5	1.421 (3)	C11—C12	1.519 (3)
C4—C12	1.539 (3)	C11—O13	1.424 (3)
O5—C6	1.439 (3)	C14—C15	1.509 (3)
C6—C7	1.505 (3)	C14—C16	1.510 (4)

C2—O1—C14	116.44 (17)	C6—C7—N8	109.04 (19)
O1—C2—O3	124.2 (2)	C7—N8—N9	113.4 (2)
O1—C2—C4	111.63 (18)	N8—N9—N10	173.7 (3)
O3—C2—C4	124.07 (19)	C6—C11—C12	102.52 (17)
C2—C4—O5	109.68 (17)	C6—C11—O13	108.97 (17)
C2—C4—C12	113.67 (18)	C12—C11—O13	110.87 (18)
O5—C4—C12	104.84 (17)	C4—C12—C11	101.61 (18)
C4—O5—C6	109.60 (16)	O1—C14—C15	106.30 (18)
O5—C6—C7	111.26 (19)	O1—C14—C16	108.05 (19)
O5—C6—C11	106.93 (16)	C15—C14—C16	113.3 (2)
C7—C6—C11	112.91 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O3ⁱ	0.82	2.08	2.897 (2)	175

Symmetry code: (i) x+1, y, z.

Acknowledgements

Financial support from the EPSRC to AAE and MPW is gratefully acknowledged.

References

Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Chakraborty, T. K., Srinivasu, P., Sakunthala, S., Kumar, S. K. & Kunwar, A. C. (2004). Tetrahedron Lett. 45, 3573–3577. Web of Science CrossRef CAS Google Scholar
Chakraborty, T. K., Srinivasu, P., Tapadar, S. & Mohan, B. K. (2004). J. Chem. Sci. 116, 187–207. Web of Science CrossRef CAS Google Scholar
Claridge, T. D. W., Long, D. D., Baker, C. M., Odell, B., Grant, G. H., Edwards, A. A., Tranter, G. E., Fleet, G. W. J. & Smith, M. D. (2005). J. Org. Chem. 70, 2082–2090. Web of Science CrossRef PubMed CAS Google Scholar
Claridge, T. D. W., Long, D. D., Hungerford, N. L., Aplin, R. T., Smith, M. D., Marquess, D. G. & Fleet, G. W. J. (1999). Tetrahedron Lett. 40, 2199–2202. Web of Science CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gruner, S. A. W., Locardi, E., Lohof, E. & Kessler, H. (2002). Chem. Rev. 102, 491–514. Web of Science CrossRef PubMed CAS Google Scholar
Hill, D. J., Mio, M. J., Prince, R. B., Hughes, T. S. & Moore, J. S. (2001). Chem. Rev. 101, 3893–4011. Web of Science CrossRef PubMed CAS Google Scholar
Hungerford, N. L., Claridge, T. D. W., Watterson, M. P. W., Aplin, R. T., Moreno, A. & Fleet, G. W. J. (2000). J. Chem. Soc. Perkin Trans. 1, pp. 3666–3679. Web of Science CrossRef Google Scholar
Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Schweizer, F. (2002). Angew. Chem. Int. Ed. 41, 231–253. Web of Science CrossRef Google Scholar
Smith, M. D., Claridge, T. D. W., Sansom, M. S. P. & Fleet, G. W. J. (2003). Org. Biomol. Chem. 1, 3647–3655. Web of Science CrossRef PubMed CAS Google Scholar
Straver, L. H. (1992). CAD-4 EXPRESS. Nonius, Delft, The Netherlands. Google Scholar
Trabocchi, A., Guarna, F. & Guarna, A. (2005). Curr. Org. Chem. 9, 1127–1153. Web of Science CrossRef CAS Google Scholar
Watkin, D. J., Prout, C. K. & Lilley, P. M. de Q. (1994). RC93. Chemical Crystallography Laboratory, Oxford, England. Google Scholar
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England. Google Scholar
Watterson, M. P., Edwards, A. A., Leach, J. A., Smith, M. D., Ichihara, O. & Fleet, G. W. J. (2003). Tetrahedron Lett. 44, 5853–5857. Web of Science CrossRef CAS Google Scholar

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Volume 62| Part 1| January 2006| Pages o363-o365

doi:10.1107/S1600536805042133

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Iso­propyl 2,5-anhydro-6-azido-3,6-dide­­oxy-D-xylo-hexonate

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Isopropyl 2,5-anhydro-6-azido-3,6-dideoxy-D-xylo-hexonate