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Synthesis of 3‐deoxy‐ D ‐ manno ‐2‐octulosonic acid (KDO)
Author(s) -
Frick Wendelin,
Krülle Thomas,
Schmidt Richard R.
Publication year - 1991
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.199119910179
Subject(s) - chemistry , diazomethane , anomer , bromide , derivative (finance) , wittig reaction , glyoxylic acid , stereochemistry , mannose , organic chemistry , financial economics , economics
[(Benzyloxy)(benzyloxycarbonyl)methyl]triphenylphosphonium bromide ( 8 ), obtained from glyoxylic acid via a convenient one‐pot procedure, reacted in a Wittig reaction with 4‐ O ‐benzyl‐2,3:5,6‐di‐ O ‐isopropylidene‐ D ‐mannose ( 7 ), readily synthesized on a large scale from D ‐mannose, to provide the KDO derivative 9 . Hydrogenolytic removal of the benzyl groups furnished directly the 4,5:7,8‐di‐ O ‐isopropylidene protected KDO 11 . Its treatment with diazomethane led to the known ester derivative 12α,ß (2:1 anomeric mixture) which could be also obtained by transesterification of 9 and subsequent hydrogenolytic debenzylation.