Amphiphilic carbohydrate-based mesogens, VI. Synthesis of a series of alkyl 1-thio-D-glucopyranosides and their regioselective reductions to 1-alkylthio-1-deoxy-D-glucitols

✍ Scribed by Dahlhoff, Wilhelm V.

• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: English
• Weight: 328 KB
• Volume: 1990
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.1990199001185

✦ Synopsis

Abstract

Alkyl 1‐thio‐α,β‐D‐glucopyranosides (hexyl to decyl, 1a–e) are prepared by reaction of penta‐O‐acetyl‐β‐D‐glucopyranose with the respective thiols in the presence of diethyl ether — trifluoroborane, followed by deacetylation. 1a–e are converted into their tetra‐O‐diethylboryl derivatives 2a–e and reduced with ethyldiboranes(6) in the presence of the catalyst 9‐methylsulfonyloxy‐9‐borabicyclo[3.3.1]nonane (9‐BBN‐mesylate, MSBBN) to give the mesogenic 1‐alkylthio‐1‐deoxy‐D‐glucitols 3a–e after deboronation.