Synthesis of the tetrasaccharide alpha-D-Glcp(1 -> 3)-alpha-D-Manp-(1 -> 2)-alpha-D-Manp-(1 -> 2)-alpha-D-Manp recognized by calreticulin/calnexin
Allbwn ymchwil: Cyfraniad at gyfnodolyn › Erthygl › adolygiad gan gymheiriaid
Fersiynau electronig
Dangosydd eitem ddigidol (DOI)
The title compound as its methyl glycoside was efficiently synthesized using a block synthesis approach. Halide-assisted glycosidations between 6-O-acetyl-2,3,4-tri-O-benzyl-α-d-glucopyranosyl iodide and ethyl 2-O-acetyl-4,6-di-O-benzyl-1-thio-α-d-mannopyranoside using triphenylphosphine oxide as promoter yielded, with complete α-selectivity, a disaccharide building block in high yield. The perbenzylated derivative of this proved to be an excellent donor affording 88% of the protected target tetrasaccharide in an NIS/AgOTf-promoted coupling to a known methyl dimannoside acceptor. Deprotection through catalytic hydrogenolysis then gave the target compound in 47% overall yield.
Allweddeiriau
Iaith wreiddiol | Saesneg |
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Tudalennau (o-i) | 2558-2562 |
Cyfnodolyn | Carbohydrate Research |
Cyfrol | 340 |
Rhif y cyfnodolyn | 16 |
Dynodwyr Gwrthrych Digidol (DOIs) | |
Statws | Cyhoeddwyd - 21 Tach 2005 |
Cyhoeddwyd yn allanol | Ie |