- Title
- The crystal structures of 3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-6-O-triphenylmethyl-α-D-glucofuranose and its azidedisplacement product
- Creator
- Clarke, Zane; Barnes, Evan; Prichard, Kate L.; Mares, Laura J.; Clegg, Jack K.; McCluskey, Adam; Houston, Todd A.; Simone, Michela I.
- Relation
- Acta Crystallographica Section E Vol. 74, p. 862-867
- Publisher Link
- http://dx.doi.org/10.1107/S205698901800765X
- Publisher
- Wiley-Blackwell
- Resource Type
- journal article
- Date
- 2018
- Description
- The effect of different leaving groups on the substitution versus elimination outcomes with C-5 D-glucose derivatives was investigated. The stereochemical configurations of 3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-6-O-triphenylmethyl-α-D-glucofuranose, C₃₆H₃₈O₈ (3) [systematic name: 1-[(3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(trityloxy)ethyl methanesulfonate], a stable intermediate, and 5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-β-L-idofuranose, C₃₅H₃₅N₃O₅ (4) [systematic name: (3aR,5S,6S,6aR)-5-[1-azido-2-(trityloxy)ethyl]-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole], a substitution product, were examined and the inversion of configuration for the azido group on C-5 in 4 was confirmed. The absolute structures of the molecules in the crystals of both compounds were confirmed by resonant scattering. In the crystal of 3, neighbouring molecules are linked by C—H...O hydrogen bonds, forming chains along the b-axis direction. The chains are linked by C—H...π interactions, forming layers parallel to the ab plane. In the crystal of 4, molecules are also linked by C—H...O hydrogen bonds, forming this time helices along the a-axis direction. The helices are linked by a number of C—H...Π interactions, forming a supramolecular framework.
- Subject
- crystal structure; iminosugar; D-glucofuranose; elimination; substitution; hydrogen bonding; C-H; Π interactions
- Identifier
- http://hdl.handle.net/1959.13/1410731
- Identifier
- uon:36223
- Identifier
- ISSN:1600-5368
- Language
- eng
- Full Text
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