Bulletin of the Chemical Society of Japan, volume 55, issue 2, pages 631-632
The Direct Synthesis of Methyl 2,4-Di-O-benzyl-α-D-xylopyranoside by the Regiospecific Benzylation of Methyl α-D-Xylopyranoside
Naohiko MORISHIMA
,
Shinkiti KOTO
,
Chiharu Kusuhara
,
Shonosuke ZEN
Publication type: Journal Article
Publication date: 1982-03-01
scimago Q2
SJR: 0.665
CiteScore: 6.4
Impact factor: 3.3
ISSN: 00092673, 13480634
General Chemistry
Abstract
The regiospecific benzylation of methyl α-D-xylopyranoside with benzyl chloride and sodium hydride produces methyl 2,4-di-O-benzyl-α-D-xylopyranoside in a 70% yield, together with the by-products, methyl 2,3- and 3,4-di-O-benzyl-α-D-xylopyranosides. The structure of the 2,4-di-O-benzyl derivative was confirmed through the alternative synthesis of the 2,3- and 3,4-di-O-benzyl derivatives via the O-isopropylidene and O-cyclohexylidene derivatives of methyl α-D-xylopyranoside.
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