A General and Diastereoselective Synthesis of 1,2-cis-Hexofuranosides from 1,2-trans-Thiofuranosyl Donors
✍ Scribed by Muriel Gelin; Vincent Ferrières; Daniel Plusquellec
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 313 KB
- Volume
- 2000
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
The general formation of 1,2-trans-thioglycofuranosides derived from D-galactose, D-glucose and D-mannose was readily accomplished starting from the corresponding alkyl glycofuranosides via per-O-acetyl-hexofuranoses as key synthons. Glycosidation of ethyl or phenyl perbenzylated 1,2-transthiofuranosides afforded disaccharides containing a nonre-
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## Abstract The configuration of trans, trans‐1,2‐dimethyl and of trans, cis‐1, 2‐dimethylethylene‐sulfite, as suggested by NMR, is in agreement with electrondiffraction results in the gas phase. The best fit to the observed diffraction intensities was obtained with a non‐planar sulfite ring, ϕ~max