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The use of 2,6-anhydro-2-thio sugar for a highly stereocontrolled glycosylation: A novel strategy for synthesis of 2,6-dideoxy-α-glycosides

✍ Scribed by Kazunobu Toshima; Satsuki Mukaiyama; Takashi Ishiyama; Kuniaki Tatsuta

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
258 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

Summarv:

A novel and efficient synthesis of 2,6-dideoxy-a-glycosides was developed by use of phenyl 2,6-anhydro-1,2-dithio-D-altropyranosides as glycosyl donors in a highly stereocontrolled glycosyla tion .

Highly stereocontrolled synthesis of 2,6-dideoxy glycosides is of considerable interest from points of view of carbohydrate chemistry and natural products synthesis. Many biologically

📜 SIMILAR VOLUMES

Highly β-stereoselective glycosylation b
Highly β-stereoselective glycosylation by use of 1-O-acetyl-2,6-anhydro-2-thio glycosyl donor for synthesis of 2,6-dideoxy-β-glycosides
✍ Kazunobu Toshima; Yuko Nozaki; Satsuki Mukaiyama; Kuniaki Tatsuta 📂 Article 📅 1992 🏛 Elsevier Science 🌐 French ⚖ 236 KB

## Gycosy1ation.r of lhe I-O-aceryl-2,6-anhydro3-thio sugar 3 with alcohols in the presence of several Lewis acids in CH2Cl2 proceeded smoothly to give the corresponding &Cl-glycosides with high srereocontrol in high yields. and the selectivity of the gIycosylaLon was highly independent on Lewis a