ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Synthesis of Chlorodeoxyglycosides and their Use in Preparation of Deoxy and Aminodeoxy SugarsIsolated secondary hydroxy groups of 2- or 3-O-benzoyl-4,6-O-benzylidene hexopyranosides 2-5 react with dichloromethylene(dimethyl)ammonium chloride (1) in pyridine stereospecifically to yield the inverse chlorodeoxy pyranosides 6-9.Methyl α-D-lyxopyranoside (11b) yields methyl 3,5-dichloro-3,5-didesoxy-2-O-dimethylcarbamoyl-α-D-arabinofuranoside (13). Methyl 6-chloro-6-desoxy-4-O-dimethylcarbamoyl-α-D-galactopyranoside is reduced to give methyl α-D-fucoside, 9 in three steps to give benzyl β-D-abequoside (16). 6 is converted into the 3-amino-3-deoxy glucoside 17 and via the 3-azido-3-deoxy compound 18 into the 3,6-diamino-3,6-diamino-3,6-didesoxy-α-D-glucopyranoside 20.
Notes:
Die isolierten sekundären Hydroxygruppen der 2- und 3-O-Benzoyl-4,6-O-benzylidenhexo-pyranoside 2-5 reagieren mit Dichlormethylen(dimethyl)ammoniumchlorid (1) in Pyridin stereospezifisch zu den inversen Chlordesoxypyranosiden 6-9. Methyl-α-D-lyxofuranosid (11b) ergibt Methyl-3,5-dichlor-3,5-didesoxy-2-O-dimethylcarbamoyl-α-D-arabinofuranosid (13). Methyl-6-chlor-6-desoxy-4-O-dimethylcarbamoyl-α-D-galactosid wird zu Methyl-α-D-fucosid reduziert, 9 in drei Schritten zu Benzyl-β-D-abequosid (16). Aus 6 wird das 3-Amino-3-desoxyglucosid 17 und über die 3-Azido-6-brom-6-desoxy-Verbindung 18 das 3,6-Diamino-3,6-didesoxyglucosid 20 gewonnen.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198319831107
