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Syntheses of a new type of chiral phosphines from glucose
Author(s) -
JiCheng Shi,
TingBin Wen,
DaXu Wu,
GeTan Lu,
MaoChun Hong,
QiuTian Liu,
BeiSheng Kang,
HanQing Wang,
ShiJie Lü
Publication year - 1996
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19960140511
Subject(s) - chemistry , regioselectivity , phosphine , stereospecificity , ring (chemistry) , medicinal chemistry , stereochemistry , catalysis , organic chemistry
Methyl 3‐deoxy‐3‐(diphenylphosphino)‐4,6‐ O ‐benzylidene‐α‐ D ‐altropyranoside (1) and methyl 2‐deoxy‐2‐(diphenylphosphino)‐4,6‐ O ‐benzylidene‐α‐ D ‐altropyranoside (2) were prepared from methyl 2,3‐anhydro‐4,6‐ O ‐benzylidene‐ O ‐ D ‐mannopyranoside and methyl 2,3‐anhydro‐4,6‐ O ‐benzylidene‐α‐ D ‐allopyranoside, respectively, via regioselective and stereospecific ring‐opening reactions in high yields. Compounds 1 and 2 were oxidized to give the corresponding phosphine oxides (S and 4).