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Synthesis of Protected N ‐Acetylchitooligosaccharide and Its Analogues: A Versatile Approach for the Synthesis of Complex Oligosaccharides of 2‐Amino‐2‐deoxy Sugar
Author(s) -
ZHU ZhenYuan,
ZHANG YongMin,
SUN Chao,
YAO YanPing
Publication year - 2008
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.200890275
Subject(s) - chemistry , stereochemistry , oligosaccharide , amine gas treating , organic chemistry
Abstract A stepwise synthesis of oligosaccharide chains containing 2‐amino‐2‐deoxy‐ D ‐glucopyranose units was elaborated as a new versatile approach for preparation of biologically important oligosaccharides having 2‐amino‐ 2‐deoxysugars. Utilizing N ‐phthalic acyl group as the protective group of amine, and phenylthiolate as the leaving group at the reducing terminal, protected N ‐acetylchitooligosaccharide and its analogues, methyl (3‐ O ‐acetyl‐4,6‐ O ‐ benzylene‐2‐deoxy‐2‐phthalimido‐ β ‐ D ‐glucopyranosyl)‐(1→4)‐3‐ O ‐acetyl‐6‐ O ‐benzyl‐2‐deoxy‐2‐phthalimido‐ β ‐ D ‐glucopyranoside 4 , methyl (3‐ O ‐acetyl‐4,6‐ O ‐benzylene‐2‐deoxy‐2‐phthalimido‐ β ‐ D ‐gluco‐pyranosyl)‐(1→4)‐ (3‐ O ‐acetyl‐6‐ O ‐benzyl‐2‐deoxy‐2‐phthalimido‐ β ‐ D ‐glucopyranosyl)‐(1→4)‐3‐ O ‐acetyl‐6‐ O ‐benzyl‐2‐deoxy‐2‐phthalimido‐ β ‐ D ‐glucopyranoside 6 , methyl (3‐ O ‐acetyl‐4,6‐ O ‐benzylene‐2‐deoxy‐2‐phthalimido‐ β ‐ D ‐glucopyranosyl)‐(1→3)‐4,6‐ O ‐benzylene‐2‐deoxy‐2‐phthalimido‐ β ‐ D ‐glucopyranoside 8 , and methyl (3‐ O ‐acetyl‐4,6‐ O ‐benzylene‐2‐deoxy‐2‐phthalimido‐ β ‐ D ‐glucopyranosyl)‐(1→3)‐(4,6‐ O ‐benzylene‐2‐deoxy‐2‐phthalimido‐ β ‐ D ‐glucopyranosyl)‐(1→3)‐4,6‐ O ‐benzylene‐2‐deoxy‐2‐phthalimido‐ β ‐ D ‐glucopyranoside 10 , were designed and synthesized by amino glucose as the starting material, which were all characterized by 1 H NMR, 13 C NMR and HRMS.