Thexyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-trichloroethoxycarbonylamino-beta-D-glucopyranoside (4), having the 3-hydroxy group unprotected, is a versatile starting material for the synthesis of glucosamine containing oligosaccharides. Thus, reaction with galactosyl donor 5 or fucosyl donor 6 afforded the desired beta(1-3)- and alpha(1-3)-linked disaccharides 7 and 8, respectively, in high yields, Reductive opening of the benzylidene moieties in 7 and 8 gave access to the 4-hydroxy groups in 9 and 10. Ensuing fucosylation of 9 or galactosylation of 10 led to Lewis A (Le(a)) and Lewis X (Le(x)) trisaccharide building blocks 13 and 14, respectively. Their transformation into glycosyl donors 19 and 20 and subsequent reaction with 3b-O-unprotected lactose derivative 23 as acceptor furnished the Le(a)- and Le(x) pentasaccharide precursors 24 and 25. Exchange of the N-trichloroethoxycarbonyl group for an N-acetyl group and removal of the O-benzyl and O-acetyl protective groups afforded the desired Le(a)- and Lex-pentasaccharides 1 and 2.

Synthesis of Lewis A and Lewis X pentasaccharides based on N-trichloroethoxycarbonyl protection / L. Manzoni, L. Lay, R.R. Schmidt. - In: JOURNAL OF CARBOHYDRATE CHEMISTRY. - ISSN 0732-8303. - 17:4-5(1998), pp. 739-758.

Synthesis of Lewis A and Lewis X pentasaccharides based on N-trichloroethoxycarbonyl protection

L. Manzoni;L. Lay
Secondo
;
1998

Abstract

Thexyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-trichloroethoxycarbonylamino-beta-D-glucopyranoside (4), having the 3-hydroxy group unprotected, is a versatile starting material for the synthesis of glucosamine containing oligosaccharides. Thus, reaction with galactosyl donor 5 or fucosyl donor 6 afforded the desired beta(1-3)- and alpha(1-3)-linked disaccharides 7 and 8, respectively, in high yields, Reductive opening of the benzylidene moieties in 7 and 8 gave access to the 4-hydroxy groups in 9 and 10. Ensuing fucosylation of 9 or galactosylation of 10 led to Lewis A (Le(a)) and Lewis X (Le(x)) trisaccharide building blocks 13 and 14, respectively. Their transformation into glycosyl donors 19 and 20 and subsequent reaction with 3b-O-unprotected lactose derivative 23 as acceptor furnished the Le(a)- and Le(x) pentasaccharide precursors 24 and 25. Exchange of the N-trichloroethoxycarbonyl group for an N-acetyl group and removal of the O-benzyl and O-acetyl protective groups afforded the desired Le(a)- and Lex-pentasaccharides 1 and 2.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/186308
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