TY - JOUR
T1 - Synthesis of tetrasaccharide repeating unit of the O-antigen from enterohemorrhagic Escherichia coli O157 in the form of its 2-(trimethylsilyl) ethyl glycoside
AU - Sarkar, Kakali
AU - Roy, Nirmolendu
N1 - Funding Information:
Financial support by the Council of Scientific and Industrial research, New Delhi, (Project No. 01/1536/98/EMR-II) is thankfully acknowledged.
Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2006/1
Y1 - 2006/1
N2 - Two α-linked disaccharide derivatives, ethyl 3,4,6-tri-O-acetyl-2- azido-2-deoxy-α-D-galactopyranosyl-(1 → 2)-4-azido-3-O-benzyl-4,6- dideoxy-1-thio-α-D-mannopyranoside (10) and 2-(trimethylsilyl)ethyl 3-O-acetyl-4-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl-(1 → 4)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside (16), were prepared from appropriate monosaccharide synthons. The disaccharide 16 was deacetylated and debenzoylated to afford the acceptor 17, which was allowed to react with the donor 10 to afford a tetrasaccharide derivative 18. This tetrasaccharide was transformed in three steps into 21, the desired repeating unit of the antigen from enterohemorrhagic E. coli type O157.
AB - Two α-linked disaccharide derivatives, ethyl 3,4,6-tri-O-acetyl-2- azido-2-deoxy-α-D-galactopyranosyl-(1 → 2)-4-azido-3-O-benzyl-4,6- dideoxy-1-thio-α-D-mannopyranoside (10) and 2-(trimethylsilyl)ethyl 3-O-acetyl-4-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl-(1 → 4)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside (16), were prepared from appropriate monosaccharide synthons. The disaccharide 16 was deacetylated and debenzoylated to afford the acceptor 17, which was allowed to react with the donor 10 to afford a tetrasaccharide derivative 18. This tetrasaccharide was transformed in three steps into 21, the desired repeating unit of the antigen from enterohemorrhagic E. coli type O157.
KW - Enterohemorrhagic Escherichia coli type O157
KW - Synthesis
KW - Tetrasaccharide
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U2 - 10.1080/07328300500495878
DO - 10.1080/07328300500495878
M3 - Article
AN - SCOPUS:33645142025
SN - 0732-8303
VL - 25
SP - 53
EP - 68
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
IS - 1
ER -