Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023501/xu2242sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023501/xu2242Isup2.hkl |
CCDC reference: 651485
The title compound was synthesized according to the procedure of Tennant-Eyles et al. (2000). The compound was crystallized from hexane/ethyl acetate solution (4:1, v/v) to yield colorless block-like crystals after a week at room temperature.
All H-atoms were refined using a riding model with C—H = 0.93 Å and Uiso=1.2Ueq(C) for aromatic, 0.98 Å and Uiso = 1.2Ueq (C) for CH, 0.97 Å and Uiso = 1.2Ueq(C) for CH2, 0.96 Å and Uiso = 1.5Ueq(C) for CH3. In the absence of significant anomalous dispersion effects, Freidel pairs were merged.
The title compound, 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside, (I), is obtained from methyl-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside with acetic anhydride, acetic acid and concentrated sulfuric acid in ice bath yields 90% as a white solid.
The title compound is a derivative of mannopyranoside, and the six-membered ring has a chair conformation. All five hydroxyl groups are substituted by three benzyloxy groups and two acetoxy groups respectively. The dihedral angles of three benzene rings are 94.4 (2)° (A/B), 103.9 (2)° (A/C), and 110.8 (2)° (B/C). The weak C–H···O hydrogen bonding helps to stabilize the crystal structure (Table 1).
For synthesis, see Tennant-Eyles et al., 2000.
Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C31H34O8 | Dx = 1.191 Mg m−3 |
Mr = 534.58 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, R3 | Cell parameters from 16963 reflections |
Hall symbol: R 3 | θ = 2.4–25.0° |
a = 24.001 (3) Å | µ = 0.09 mm−1 |
c = 13.441 (3) Å | T = 298 K |
V = 6705.5 (19) Å3 | Block, colorless |
Z = 9 | 0.50 × 0.45 × 0.25 mm |
F(000) = 2556 |
Rigaku R-AXIS RAPID IP diffractometer | 1277 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.056 |
Graphite monochromator | θmax = 25.0°, θmin = 2.4° |
Detector resolution: 10.00 pixels mm-1 | h = −28→28 |
Ω scans | k = −28→26 |
16963 measured reflections | l = −13→15 |
2627 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0156P)2 + 0.731P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2627 reflections | Δρmax = 0.26 e Å−3 |
319 parameters | Δρmin = −0.19 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00248 (10) |
C31H34O8 | Z = 9 |
Mr = 534.58 | Mo Kα radiation |
Trigonal, R3 | µ = 0.09 mm−1 |
a = 24.001 (3) Å | T = 298 K |
c = 13.441 (3) Å | 0.50 × 0.45 × 0.25 mm |
V = 6705.5 (19) Å3 |
Rigaku R-AXIS RAPID IP diffractometer | 1277 reflections with I > 2σ(I) |
16963 measured reflections | Rint = 0.056 |
2627 independent reflections |
R[F2 > 2σ(F2)] = 0.053 | 1 restraint |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.26 e Å−3 |
2627 reflections | Δρmin = −0.19 e Å−3 |
319 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.8308 (2) | 0.89609 (18) | 0.0017 (3) | 0.0589 (11) | |
O2 | 0.7086 (2) | 0.8907 (2) | 0.0209 (3) | 0.0832 (14) | |
O3 | 0.6777 (4) | 0.9119 (4) | 0.1583 (6) | 0.169 (3) | |
O4 | 0.71440 (19) | 0.72464 (19) | 0.0247 (3) | 0.0593 (11) | |
O5 | 0.8332 (2) | 0.7232 (2) | 0.0228 (3) | 0.0640 (12) | |
O6 | 0.9087 (2) | 0.8540 (2) | 0.0925 (3) | 0.0690 (13) | |
O7 | 0.86749 (18) | 0.88162 (18) | −0.1512 (3) | 0.0562 (11) | |
O8 | 0.9173 (2) | 0.9883 (2) | −0.1794 (4) | 0.0791 (14) | |
C1 | 0.7701 (3) | 0.8374 (3) | 0.0044 (4) | 0.0516 (16) | |
H1A | 0.7513 | 0.8282 | −0.0624 | 0.062* | |
C2 | 0.7752 (3) | 0.7796 (3) | 0.0409 (4) | 0.0506 (16) | |
H2A | 0.7851 | 0.7841 | 0.1122 | 0.061* | |
C3 | 0.8278 (3) | 0.7760 (3) | −0.0153 (4) | 0.0547 (17) | |
H3A | 0.8152 | 0.7675 | −0.0855 | 0.066* | |
C4 | 0.8894 (3) | 0.8393 (3) | −0.0087 (4) | 0.0570 (17) | |
H4A | 0.9232 | 0.8373 | −0.0470 | 0.068* | |
C5 | 0.8803 (3) | 0.8924 (3) | −0.0467 (5) | 0.0568 (17) | |
H5A | 0.9205 | 0.9332 | −0.0374 | 0.068* | |
C6 | 0.7279 (3) | 0.8491 (3) | 0.0724 (5) | 0.0680 (19) | |
H6A | 0.6902 | 0.8086 | 0.0900 | 0.082* | |
H6B | 0.7510 | 0.8697 | 0.1330 | 0.082* | |
C7 | 0.6824 (4) | 0.9177 (5) | 0.0706 (7) | 0.105 (3) | |
C8 | 0.6651 (5) | 0.9575 (4) | 0.0146 (7) | 0.128 (3) | |
H8A | 0.6391 | 0.9685 | 0.0550 | 0.192* | |
H8B | 0.6412 | 0.9345 | −0.0433 | 0.192* | |
H8C | 0.7033 | 0.9960 | −0.0055 | 0.192* | |
C9 | 0.6919 (3) | 0.6800 (3) | 0.1058 (5) | 0.077 (2) | |
H9A | 0.6883 | 0.7004 | 0.1658 | 0.092* | |
H9B | 0.7212 | 0.6640 | 0.1183 | 0.092* | |
C10 | 0.6280 (2) | 0.6269 (3) | 0.0754 (4) | 0.0682 (19) | |
C11 | 0.5738 (3) | 0.6333 (3) | 0.0843 (4) | 0.125 (3) | |
H11A | 0.5774 | 0.6706 | 0.1116 | 0.150* | |
C12 | 0.5143 (2) | 0.5841 (4) | 0.0526 (5) | 0.160 (4) | |
H12A | 0.4780 | 0.5884 | 0.0586 | 0.192* | |
C13 | 0.5090 (3) | 0.5284 (3) | 0.0118 (4) | 0.132 (4) | |
H13A | 0.4691 | 0.4955 | −0.0094 | 0.158* | |
C14 | 0.5631 (4) | 0.5220 (3) | 0.0028 (4) | 0.144 (4) | |
H14A | 0.5596 | 0.4847 | −0.0244 | 0.173* | |
C15 | 0.6227 (3) | 0.5712 (3) | 0.0346 (4) | 0.105 (3) | |
H15A | 0.6589 | 0.5669 | 0.0286 | 0.126* | |
C16 | 0.8486 (4) | 0.6916 (4) | −0.0499 (5) | 0.094 (2) | |
H16A | 0.8883 | 0.7223 | −0.0824 | 0.113* | |
H16B | 0.8149 | 0.6741 | −0.0998 | 0.113* | |
C17 | 0.8561 (2) | 0.63855 (18) | −0.0072 (3) | 0.0570 (17) | |
C18 | 0.8460 (2) | 0.6219 (2) | 0.0929 (3) | 0.0638 (17) | |
H18A | 0.8323 | 0.6431 | 0.1357 | 0.077* | |
C19 | 0.8564 (2) | 0.5736 (2) | 0.1290 (3) | 0.0689 (18) | |
H19A | 0.8497 | 0.5624 | 0.1960 | 0.083* | |
C20 | 0.8769 (2) | 0.54193 (18) | 0.0651 (4) | 0.076 (2) | |
H20A | 0.8839 | 0.5096 | 0.0893 | 0.091* | |
C21 | 0.8870 (2) | 0.5586 (2) | −0.0350 (4) | 0.081 (2) | |
H21A | 0.9007 | 0.5374 | −0.0778 | 0.097* | |
C22 | 0.8766 (2) | 0.6069 (2) | −0.0712 (2) | 0.0679 (19) | |
H22A | 0.8834 | 0.6180 | −0.1381 | 0.082* | |
C23 | 0.9567 (4) | 0.8403 (5) | 0.1229 (6) | 0.111 (3) | |
H23A | 0.9962 | 0.8663 | 0.0861 | 0.133* | |
H23B | 0.9429 | 0.7953 | 0.1120 | 0.133* | |
C24 | 0.9667 (4) | 0.8558 (4) | 0.2296 (4) | 0.097 (3) | |
C25 | 1.0186 (3) | 0.9125 (4) | 0.2651 (6) | 0.131 (3) | |
H25A | 1.0479 | 0.9426 | 0.2207 | 0.157* | |
C26 | 1.0267 (3) | 0.9240 (3) | 0.3668 (7) | 0.176 (5) | |
H26A | 1.0615 | 0.9619 | 0.3905 | 0.212* | |
C27 | 0.9830 (5) | 0.8790 (5) | 0.4332 (4) | 0.169 (5) | |
H27A | 0.9885 | 0.8867 | 0.5013 | 0.203* | |
C28 | 0.9311 (4) | 0.8223 (4) | 0.3978 (5) | 0.165 (5) | |
H28A | 0.9019 | 0.7922 | 0.4422 | 0.198* | |
C29 | 0.9230 (3) | 0.8108 (3) | 0.2960 (6) | 0.140 (4) | |
H29A | 0.8883 | 0.7729 | 0.2723 | 0.169* | |
C30 | 0.8914 (3) | 0.9350 (4) | −0.2107 (5) | 0.0642 (19) | |
C31 | 0.8804 (4) | 0.9152 (4) | −0.3171 (5) | 0.089 (2) | |
H31A | 0.9109 | 0.9500 | −0.3578 | 0.134* | |
H31B | 0.8375 | 0.9044 | −0.3358 | 0.134* | |
H31C | 0.8856 | 0.8784 | −0.3264 | 0.134* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.066 (3) | 0.048 (3) | 0.062 (3) | 0.027 (3) | 0.005 (2) | 0.001 (2) |
O2 | 0.113 (4) | 0.092 (4) | 0.078 (3) | 0.076 (3) | 0.025 (3) | 0.018 (3) |
O3 | 0.139 (7) | 0.125 (7) | 0.106 (5) | 0.086 (6) | 0.054 (5) | 0.036 (5) |
O4 | 0.062 (3) | 0.053 (3) | 0.049 (3) | 0.019 (2) | −0.004 (2) | 0.011 (2) |
O5 | 0.097 (3) | 0.066 (3) | 0.048 (3) | 0.055 (3) | 0.009 (2) | 0.000 (2) |
O6 | 0.065 (3) | 0.084 (3) | 0.063 (3) | 0.041 (3) | −0.014 (2) | 0.000 (2) |
O7 | 0.059 (3) | 0.051 (3) | 0.051 (2) | 0.021 (2) | 0.002 (2) | 0.007 (2) |
O8 | 0.068 (3) | 0.057 (3) | 0.100 (4) | 0.022 (3) | −0.002 (3) | 0.012 (3) |
C1 | 0.060 (4) | 0.054 (4) | 0.043 (3) | 0.030 (4) | 0.001 (3) | 0.004 (3) |
C2 | 0.058 (4) | 0.048 (4) | 0.044 (4) | 0.025 (4) | −0.003 (3) | 0.002 (3) |
C3 | 0.065 (5) | 0.051 (4) | 0.052 (4) | 0.031 (4) | −0.005 (3) | −0.005 (3) |
C4 | 0.059 (4) | 0.059 (5) | 0.049 (4) | 0.027 (4) | 0.001 (3) | 0.002 (3) |
C5 | 0.055 (4) | 0.051 (4) | 0.060 (5) | 0.024 (3) | −0.006 (4) | −0.001 (3) |
C6 | 0.083 (5) | 0.074 (5) | 0.061 (4) | 0.049 (4) | 0.017 (4) | 0.017 (4) |
C7 | 0.143 (8) | 0.133 (8) | 0.082 (7) | 0.101 (7) | 0.046 (6) | 0.037 (6) |
C8 | 0.141 (7) | 0.129 (6) | 0.112 (7) | 0.116 (6) | 0.023 (6) | 0.028 (6) |
C9 | 0.068 (4) | 0.067 (4) | 0.079 (5) | 0.021 (4) | −0.002 (4) | 0.019 (4) |
C10 | 0.091 (5) | 0.084 (5) | 0.077 (4) | 0.026 (4) | 0.004 (4) | 0.021 (4) |
C11 | 0.092 (6) | 0.114 (6) | 0.160 (8) | 0.044 (5) | −0.012 (5) | 0.013 (6) |
C12 | 0.131 (6) | 0.131 (7) | 0.170 (7) | 0.069 (5) | −0.021 (5) | 0.033 (6) |
C13 | 0.119 (7) | 0.115 (7) | 0.080 (6) | −0.003 (5) | −0.027 (5) | 0.022 (5) |
C14 | 0.141 (9) | 0.102 (7) | 0.102 (6) | 0.026 (6) | 0.024 (7) | −0.002 (5) |
C15 | 0.120 (6) | 0.076 (5) | 0.097 (6) | 0.031 (5) | 0.028 (5) | 0.011 (5) |
C16 | 0.094 (7) | 0.080 (5) | 0.062 (5) | 0.056 (5) | 0.010 (4) | 0.011 (4) |
C17 | 0.065 (4) | 0.054 (4) | 0.055 (4) | 0.032 (4) | 0.010 (3) | −0.005 (3) |
C18 | 0.086 (5) | 0.063 (4) | 0.061 (5) | 0.051 (4) | 0.004 (4) | −0.001 (4) |
C19 | 0.078 (5) | 0.066 (5) | 0.070 (4) | 0.041 (4) | −0.002 (4) | −0.005 (4) |
C20 | 0.084 (5) | 0.071 (5) | 0.088 (6) | 0.051 (4) | −0.004 (4) | −0.006 (5) |
C21 | 0.091 (6) | 0.096 (6) | 0.063 (5) | 0.053 (5) | 0.007 (4) | −0.014 (4) |
C22 | 0.082 (5) | 0.075 (5) | 0.062 (4) | 0.050 (4) | 0.012 (4) | −0.003 (4) |
C23 | 0.080 (6) | 0.132 (7) | 0.084 (5) | 0.064 (5) | −0.015 (5) | 0.007 (5) |
C24 | 0.092 (6) | 0.133 (7) | 0.085 (6) | 0.041 (5) | −0.030 (5) | 0.008 (6) |
C25 | 0.106 (8) | 0.131 (9) | 0.162 (11) | 0.063 (8) | −0.026 (7) | −0.002 (8) |
C26 | 0.135 (9) | 0.153 (9) | 0.160 (9) | 0.073 (7) | −0.036 (8) | −0.032 (8) |
C27 | 0.151 (15) | 0.162 (13) | 0.105 (8) | 0.061 (12) | −0.044 (10) | −0.058 (10) |
C28 | 0.189 (9) | 0.157 (8) | 0.101 (8) | 0.072 (7) | −0.027 (7) | 0.021 (6) |
C29 | 0.199 (11) | 0.153 (10) | 0.066 (6) | 0.084 (9) | −0.044 (7) | −0.007 (6) |
C30 | 0.047 (4) | 0.066 (5) | 0.078 (5) | 0.028 (4) | 0.008 (4) | 0.015 (4) |
C31 | 0.110 (6) | 0.104 (6) | 0.057 (5) | 0.055 (5) | 0.019 (4) | 0.023 (4) |
O1—C5 | 1.396 (7) | C12—H12A | 0.9300 |
O1—C1 | 1.434 (7) | C13—C14 | 1.3900 |
O2—C7 | 1.291 (9) | C13—H13A | 0.9300 |
O2—C6 | 1.469 (7) | C14—C15 | 1.3900 |
O3—C7 | 1.186 (9) | C14—H14A | 0.9300 |
O4—C2 | 1.411 (6) | C15—H15A | 0.9300 |
O4—C9 | 1.431 (7) | C16—C17 | 1.487 (7) |
O5—C16 | 1.395 (7) | C16—H16A | 0.9700 |
O5—C3 | 1.433 (7) | C16—H16B | 0.9700 |
O6—C23 | 1.409 (8) | C17—C18 | 1.3900 |
O6—C4 | 1.423 (6) | C17—C22 | 1.3900 |
O7—C30 | 1.369 (7) | C18—C19 | 1.3900 |
O7—C5 | 1.433 (6) | C18—H18A | 0.9300 |
O8—C30 | 1.186 (7) | C19—C20 | 1.3900 |
C1—C6 | 1.490 (8) | C19—H19A | 0.9300 |
C1—C2 | 1.534 (7) | C20—C21 | 1.3900 |
C1—H1A | 0.9800 | C20—H20A | 0.9300 |
C2—C3 | 1.509 (8) | C21—C22 | 1.3900 |
C2—H2A | 0.9800 | C21—H21A | 0.9300 |
C3—C4 | 1.501 (8) | C22—H22A | 0.9300 |
C3—H3A | 0.9800 | C23—C24 | 1.472 (9) |
C4—C5 | 1.488 (8) | C23—H23A | 0.9700 |
C4—H4A | 0.9800 | C23—H23B | 0.9700 |
C5—H5A | 0.9800 | C24—C25 | 1.3900 |
C6—H6A | 0.9700 | C24—C29 | 1.3900 |
C6—H6B | 0.9700 | C25—C26 | 1.3900 |
C7—C8 | 1.430 (11) | C25—H25A | 0.9300 |
C8—H8A | 0.9600 | C26—C27 | 1.3900 |
C8—H8B | 0.9600 | C26—H26A | 0.9300 |
C8—H8C | 0.9600 | C27—C28 | 1.3900 |
C9—C10 | 1.479 (7) | C27—H27A | 0.9300 |
C9—H9A | 0.9700 | C28—C29 | 1.3900 |
C9—H9B | 0.9700 | C28—H28A | 0.9300 |
C10—C11 | 1.3900 | C29—H29A | 0.9300 |
C10—C15 | 1.3900 | C30—C31 | 1.490 (9) |
C11—C12 | 1.3900 | C31—H31A | 0.9600 |
C11—H11A | 0.9300 | C31—H31B | 0.9600 |
C12—C13 | 1.3900 | C31—H31C | 0.9600 |
C5—O1—C1 | 115.4 (4) | C12—C13—C14 | 120.0 |
C7—O2—C6 | 119.7 (6) | C12—C13—H13A | 120.0 |
C2—O4—C9 | 114.1 (5) | C14—C13—H13A | 120.0 |
C16—O5—C3 | 113.4 (4) | C15—C14—C13 | 120.0 |
C23—O6—C4 | 114.9 (5) | C15—C14—H14A | 120.0 |
C30—O7—C5 | 116.9 (5) | C13—C14—H14A | 120.0 |
O1—C1—C6 | 106.5 (5) | C14—C15—C10 | 120.0 |
O1—C1—C2 | 113.3 (5) | C14—C15—H15A | 120.0 |
C6—C1—C2 | 110.1 (5) | C10—C15—H15A | 120.0 |
O1—C1—H1A | 109.0 | O5—C16—C17 | 111.9 (5) |
C6—C1—H1A | 109.0 | O5—C16—H16A | 109.2 |
C2—C1—H1A | 109.0 | C17—C16—H16A | 109.2 |
O4—C2—C3 | 111.9 (5) | O5—C16—H16B | 109.2 |
O4—C2—C1 | 106.4 (5) | C17—C16—H16B | 109.2 |
C3—C2—C1 | 109.8 (5) | H16A—C16—H16B | 107.9 |
O4—C2—H2A | 109.6 | C18—C17—C22 | 120.0 |
C3—C2—H2A | 109.6 | C18—C17—C16 | 122.7 (4) |
C1—C2—H2A | 109.6 | C22—C17—C16 | 117.2 (4) |
O5—C3—C4 | 113.1 (5) | C19—C18—C17 | 120.0 |
O5—C3—C2 | 108.6 (5) | C19—C18—H18A | 120.0 |
C4—C3—C2 | 110.1 (5) | C17—C18—H18A | 120.0 |
O5—C3—H3A | 108.3 | C18—C19—C20 | 120.0 |
C4—C3—H3A | 108.3 | C18—C19—H19A | 120.0 |
C2—C3—H3A | 108.3 | C20—C19—H19A | 120.0 |
O6—C4—C5 | 106.5 (5) | C21—C20—C19 | 120.0 |
O6—C4—C3 | 109.9 (5) | C21—C20—H20A | 120.0 |
C5—C4—C3 | 110.6 (5) | C19—C20—H20A | 120.0 |
O6—C4—H4A | 109.9 | C20—C21—C22 | 120.0 |
C5—C4—H4A | 109.9 | C20—C21—H21A | 120.0 |
C3—C4—H4A | 109.9 | C22—C21—H21A | 120.0 |
O1—C5—O7 | 110.8 (5) | C21—C22—C17 | 120.0 |
O1—C5—C4 | 112.9 (5) | C21—C22—H22A | 120.0 |
O7—C5—C4 | 107.0 (5) | C17—C22—H22A | 120.0 |
O1—C5—H5A | 108.7 | O6—C23—C24 | 105.8 (6) |
O7—C5—H5A | 108.7 | O6—C23—H23A | 110.6 |
C4—C5—H5A | 108.7 | C24—C23—H23A | 110.6 |
O2—C6—C1 | 108.3 (5) | O6—C23—H23B | 110.6 |
O2—C6—H6A | 110.0 | C24—C23—H23B | 110.6 |
C1—C6—H6A | 110.0 | H23A—C23—H23B | 108.7 |
O2—C6—H6B | 110.0 | C25—C24—C29 | 120.0 |
C1—C6—H6B | 110.0 | C25—C24—C23 | 122.3 (7) |
H6A—C6—H6B | 108.4 | C29—C24—C23 | 117.7 (7) |
O3—C7—O2 | 119.9 (8) | C26—C25—C24 | 120.0 |
O3—C7—C8 | 123.9 (9) | C26—C25—H25A | 120.0 |
O2—C7—C8 | 116.0 (8) | C24—C25—H25A | 120.0 |
C7—C8—H8A | 109.5 | C25—C26—C27 | 120.0 |
C7—C8—H8B | 109.5 | C25—C26—H26A | 120.0 |
H8A—C8—H8B | 109.5 | C27—C26—H26A | 120.0 |
C7—C8—H8C | 109.5 | C28—C27—C26 | 120.0 |
H8A—C8—H8C | 109.5 | C28—C27—H27A | 120.0 |
H8B—C8—H8C | 109.5 | C26—C27—H27A | 120.0 |
O4—C9—C10 | 106.0 (5) | C27—C28—C29 | 120.0 |
O4—C9—H9A | 110.5 | C27—C28—H28A | 120.0 |
C10—C9—H9A | 110.5 | C29—C28—H28A | 120.0 |
O4—C9—H9B | 110.5 | C28—C29—C24 | 120.0 |
C10—C9—H9B | 110.5 | C28—C29—H29A | 120.0 |
H9A—C9—H9B | 108.7 | C24—C29—H29A | 120.0 |
C11—C10—C15 | 120.0 | O8—C30—O7 | 123.5 (7) |
C11—C10—C9 | 120.3 (6) | O8—C30—C31 | 126.8 (7) |
C15—C10—C9 | 119.7 (6) | O7—C30—C31 | 109.8 (6) |
C10—C11—C12 | 120.0 | C30—C31—H31A | 109.5 |
C10—C11—H11A | 120.0 | C30—C31—H31B | 109.5 |
C12—C11—H11A | 120.0 | H31A—C31—H31B | 109.5 |
C13—C12—C11 | 120.0 | C30—C31—H31C | 109.5 |
C13—C12—H12A | 120.0 | H31A—C31—H31C | 109.5 |
C11—C12—H12A | 120.0 | H31B—C31—H31C | 109.5 |
C5—O1—C1—C6 | 171.0 (5) | O4—C9—C10—C11 | −80.9 (6) |
C5—O1—C1—C2 | 49.9 (6) | O4—C9—C10—C15 | 97.0 (5) |
C9—O4—C2—C3 | 103.7 (6) | C15—C10—C11—C12 | 0.0 |
C9—O4—C2—C1 | −136.4 (5) | C9—C10—C11—C12 | 177.9 (5) |
O1—C1—C2—O4 | −171.0 (5) | C10—C11—C12—C13 | 0.0 |
C6—C1—C2—O4 | 69.9 (6) | C11—C12—C13—C14 | 0.0 |
O1—C1—C2—C3 | −49.7 (6) | C12—C13—C14—C15 | 0.0 |
C6—C1—C2—C3 | −168.7 (5) | C13—C14—C15—C10 | 0.0 |
C16—O5—C3—C4 | −92.8 (7) | C11—C10—C15—C14 | 0.0 |
C16—O5—C3—C2 | 144.7 (6) | C9—C10—C15—C14 | −177.9 (5) |
O4—C2—C3—O5 | −64.3 (6) | C3—O5—C16—C17 | 178.0 (5) |
C1—C2—C3—O5 | 177.8 (5) | O5—C16—C17—C18 | 2.6 (8) |
O4—C2—C3—C4 | 171.3 (5) | O5—C16—C17—C22 | −174.8 (4) |
C1—C2—C3—C4 | 53.4 (6) | C22—C17—C18—C19 | 0.0 |
C23—O6—C4—C5 | −140.2 (6) | C16—C17—C18—C19 | −177.4 (5) |
C23—O6—C4—C3 | 99.9 (7) | C17—C18—C19—C20 | 0.0 |
O5—C3—C4—O6 | −61.1 (7) | C18—C19—C20—C21 | 0.0 |
C2—C3—C4—O6 | 60.6 (6) | C19—C20—C21—C22 | 0.0 |
O5—C3—C4—C5 | −178.4 (5) | C20—C21—C22—C17 | 0.0 |
C2—C3—C4—C5 | −56.7 (7) | C18—C17—C22—C21 | 0.0 |
C1—O1—C5—O7 | 67.4 (6) | C16—C17—C22—C21 | 177.5 (5) |
C1—O1—C5—C4 | −52.6 (7) | C4—O6—C23—C24 | −177.2 (6) |
C30—O7—C5—O1 | 91.6 (6) | O6—C23—C24—C25 | −101.6 (7) |
C30—O7—C5—C4 | −144.9 (5) | O6—C23—C24—C29 | 80.1 (7) |
O6—C4—C5—O1 | −63.7 (6) | C29—C24—C25—C26 | 0.0 |
C3—C4—C5—O1 | 55.7 (7) | C23—C24—C25—C26 | −178.3 (6) |
O6—C4—C5—O7 | 174.1 (4) | C24—C25—C26—C27 | 0.0 |
C3—C4—C5—O7 | −66.5 (6) | C25—C26—C27—C28 | 0.0 |
C7—O2—C6—C1 | −166.6 (7) | C26—C27—C28—C29 | 0.0 |
O1—C1—C6—O2 | 73.5 (6) | C27—C28—C29—C24 | 0.0 |
C2—C1—C6—O2 | −163.3 (5) | C25—C24—C29—C28 | 0.0 |
C6—O2—C7—O3 | 4.6 (14) | C23—C24—C29—C28 | 178.4 (6) |
C6—O2—C7—C8 | −180.0 (7) | C5—O7—C30—O8 | −5.9 (9) |
C2—O4—C9—C10 | 179.4 (5) | C5—O7—C30—C31 | 173.5 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23A···O1i | 0.97 | 2.53 | 3.496 (9) | 175 |
Symmetry code: (i) −y+2, x−y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C31H34O8 |
Mr | 534.58 |
Crystal system, space group | Trigonal, R3 |
Temperature (K) | 298 |
a, c (Å) | 24.001 (3), 13.441 (3) |
V (Å3) | 6705.5 (19) |
Z | 9 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.45 × 0.25 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16963, 2627, 1277 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.089, 1.03 |
No. of reflections | 2627 |
No. of parameters | 319 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.19 |
Computer programs: DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23A···O1i | 0.97 | 2.53 | 3.496 (9) | 175 |
Symmetry code: (i) −y+2, x−y+1, z. |
The title compound, 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside, (I), is obtained from methyl-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside with acetic anhydride, acetic acid and concentrated sulfuric acid in ice bath yields 90% as a white solid.
The title compound is a derivative of mannopyranoside, and the six-membered ring has a chair conformation. All five hydroxyl groups are substituted by three benzyloxy groups and two acetoxy groups respectively. The dihedral angles of three benzene rings are 94.4 (2)° (A/B), 103.9 (2)° (A/C), and 110.8 (2)° (B/C). The weak C–H···O hydrogen bonding helps to stabilize the crystal structure (Table 1).