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Synthese von N ‐Acetyl‐ D ‐ und ‐ L ‐glucosamin, cis ‐3,5‐Cyclohexadien‐1,2‐diol als Baustein für die Gewinnung modifizierter Hexosen
Author(s) -
Lehmann Jochen,
Moritz Andreas
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.1991199101160
Subject(s) - chemistry , stereochemistry , glucosamine , diol , organic chemistry
Synthesis of N ‐Acetyl‐ D ‐ and ‐ L ‐glucosamine, cis ‐3,5‐Cyclohexadiene‐1,2‐diol as Building Block for the Preparation of Modified Hexoses Six‐membered, unsaturated carbocycles are versatile starting materials for the preparation of a large variety of modified hexoses. This is exemplified by the synthesis of N ‐acetylglucosamine 12 as a racemate from cis ‐3,5‐cyclohexadiene‐1,2‐diol ( 1 ), which can be obtained by microbial oxidation of benzene. In this special case D ‐ and L ‐ N ‐acetylglucosamine could be differentiated by enzymatic D ‐galactosylation of the former.