Premium
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
Author(s) -
Dahlhoff Wilhelm V.
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1990199001185
Subject(s) - chemistry , regioselectivity , alkyl , pyridinium , thio , ether , carbohydrate , medicinal chemistry , glycoside , anomer , alkoxy group , stereochemistry , catalysis , organic chemistry
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.