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<atl>Synthesis of α-Manp-(1→2)-α-Manp-(1→3)-α-Manp-(1→3)-Manp, the tetrasaccharide repeating unit of Escherichia coli O9a, and α-Manp-(1→2)-α-Manp-(1→2)-α-Manp-(1→3)-α-Manp-(1→3)-Manp, the pentasaccharide repeating unit of E. coli O9 and Klebsiella O3
- Source :
-
Carbohydrate Research . Mar2002, Vol. 337 Issue 5, p383. 8p. - Publication Year :
- 2002
-
Abstract
- The tetrasaccharide repeating unit of Escherichia coli O9a, α-d-Manp-(1→2)-α-d-Manp-(1→3)-α-d-Manp-(1→3)-d-Manp, and the pentasaccharide repeating unit of E. coli O9 and Klebsiella O3, α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp-(1→3)-α-d-Manp-(1→3)-d-Manp, were synthesized as their methyl glycosides. Thus, selective 3-O-allylation of p-methoxyphenyl α-d-mannopyranoside via a dibutyltin intermediate gave p-methoxyphenyl 3-O-allyl-α-d-mannopyranoside (2) in good yield. Benzoylation (→3), then removal of 1-O-methoxyphenyl (→4), and subsequent trichloroacetimidation afforded the 3-O-allyl-2,4,6-tri-O-benzoyl-α-d-mannopyranosyl trichloroacetimidate (5). Condensation of 5 with methyl 4,6-O-benzylidene-α-d-mannopyranoside (6) selectively afforded the (1→3)-linked disaccharide 7. Benzoylation of 7, debenzylidenation, benzoylation, and deallylation gave methyl 2,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1→3)-2,4,6-tri-O-benzoyl-α-d-mannopyranoside (11) as the disaccharide acceptor. Coupling of 11 with (1→2)-linked mannose disaccharide donor 17 or trisaccharide donor 21, followed by deacylation, furnished the target tetrasaccharide and pentasaccharide, respectively. [Copyright &y& Elsevier]
- Subjects :
- *OLIGOSACCHARIDES
*MANNOSE
*ESCHERICHIA coli
Subjects
Details
- Language :
- English
- ISSN :
- 00086215
- Volume :
- 337
- Issue :
- 5
- Database :
- Academic Search Index
- Journal :
- Carbohydrate Research
- Publication Type :
- Academic Journal
- Accession number :
- 7756326
- Full Text :
- https://doi.org/10.1016/S0008-6215(02)00011-3