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Chemical Synthesis of a Tetrasaccharide Fragment Related to the Exopolysaccharide of Arthrobacter sp. CE‐17
Author(s) -
Lemanski Gregor,
Ziegler Thomas
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200001)2000:1<181::aid-ejoc181>3.0.co;2-7
Subject(s) - chemistry , tetrasaccharide , disaccharide , thio , stereochemistry , glycoside , intramolecular force , organic chemistry , polysaccharide
The tetrasaccharide 5‐aminopentyl glycoside β‐ D ‐Man p ‐(1→4)‐β‐ D ‐Glc p ‐(1→4)‐α‐ L ‐Rha p ‐(1→3)‐β‐ D ‐Glc p ‐1‐ O ‐(CH 2 ) 5 NH 2 ( 22 ) related to the exopolysaccharide of Arthrobacter sp. CE‐17 was synthesized by coupling of the properly protected disaccharide blocks β‐ D ‐Man p ‐(1→4)‐β‐ D ‐Glc p ‐1‐ S ‐Ph ( 11 ) and α‐ L ‐Rha p ‐(1→3)‐β‐ D ‐Glc p ‐1‐ O ‐(CH 2 ) 5 NHZ ( 20 ). Building block 11 was obtained by intramolecular β‐mannosylation of a malonyl‐tethered disaccharide glycoside which was prepared from phenyl 4,6‐ O ‐benzylidene‐1‐thio‐β‐ D ‐glucopyranoside ( 1 ) and ethyl 2,3,4‐tri‐ O ‐benzyl‐1‐thio‐α‐ D ‐mannopyranoside ( 5 ) in 5 steps. Building block 20 was obtained by coupling N ‐Z‐protected 5‐aminopentyl 2‐ O ‐benzyl‐4,6‐ O ‐benzylidene‐β‐ D ‐glucopyranoside ( 14 ) obtained from the non‐benzylated counterpart 12 with ethyl 2,3‐di‐ O ‐benzoyl‐4‐ O ‐chloroacetyl‐1‐thio‐α‐ L ‐rhamnopyranoside ( 18 ) obtained in 3 steps from ethyl 2,3‐ O ‐isopropylidene‐1‐thio‐α‐ L ‐rhamnopyranoside ( 15 ).