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Synthesis of the 6-deoxytalose-containing tetrasaccharide of the glycopeptidolipid from Mycobacterium intracellare serotype 7
- Source :
-
Carbohydrate Research . Dec2008, Vol. 343 Issue 18, p3107-3111. 5p. - Publication Year :
- 2008
-
Abstract
- Abstract: An efficient synthesis of 4-methoxyphenyl α-l-Rhap-(1→3)-α-l-Rhap-(1→3)-α-l-Rhap-(1→2)-6-deoxy-α-l-Talp, the tetrasaccharide related to the GPLs of Mycobacterium intracellare serotype 7, was achieved with 4-methoxyphenyl 3,4-di-O-benzoyl-6-deoxy-α-l-talopyranoside (6c) as the key intermediate which was obtained through selective 3-O-benzoylation of 4-O-benzoyl-6-deoxy-α-l-taloside. Coupling of 6c with 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-α-l-rhamnopyranosyl trichloroacetimidate followed by removal of the allyloxycarbonyl protecting group afforded the disaccharide acceptor 11. Condensation of 11 with 2,3,4-tri-O-benzoyl-α-l-rhamnopyranosyl-(1→3)-2,4-di-O-benzoyl-α-l-rhamnopyranosyl trichloroacetimidate and subsequent deprotection gave the target tetrasaccharide. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00086215
- Volume :
- 343
- Issue :
- 18
- Database :
- Academic Search Index
- Journal :
- Carbohydrate Research
- Publication Type :
- Academic Journal
- Accession number :
- 35073795
- Full Text :
- https://doi.org/10.1016/j.carres.2008.09.010