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Details for article 92 of 116 found articles
| Title: |
Synthesis of Lewis a and Lewis X Pentasaccharides Based on N-Trichloroethoxycarbonyl Protection |
| Author: |
Manzoni, Leonardo Lay, Luigi Schmidt, Richard R. |
| Appeared in: |
Journal of carbohydrate chemistry |
| Paging: | Volume 17 (1998) nr. 4-5 pages 739-758 |
| Year: |
1998-05-01 |
| Contents: |
Thexyldimethylsilyl 4,6-O-benzylidene-2-deoxy-2-trichloroethoxycarbonylamino-β-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 β(1-3)- and α(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 (Lea) and Lewis X (Lex) 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 Lea- and Lex 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 Lea- and Lex- pentasaccharides 1 and 2. |
| Publisher: |
Taylor & Francis |
| Source file: |
Elektronische Wetenschappelijke Tijdschriften |
Details for article 92 of 116 found articles
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