Synthesis of N-(9-fluoren ylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-serine
10.3724/SP.J.1008.2011.01227
- Author:
Xiang LI
1
Author Information
1. Department of Organic Chemistry
- Publication Type:Journal Article
- Keywords:
Galactose;
Glyco amino adds;
Serine;
Synthesis
- From:
Academic Journal of Second Military Medical University
2011;32(11):1227-1230
- CountryChina
- Language:Chinese
-
Abstract:
Objeciive To obtain fully protected glyco amino acid for synthesis of various glycopeptides. Methods With galactose as the Initial compound, the full benzyl protected β-D-1-thio-galactopyranoeide (5) was obtained after 5 steps of reactions. Then it was used as donor for glycosylation with Fmoc-Ser-OAlly to yield fully protected glyco amino add. Fmally, the allyl group was removed to obtain the objeciive glyco amino add (1). Resulis The structures of the intermediate and objective compounds were confirmed by MS, 1HNMR and 13CNMR, and the target glyco amino add was obtained. Conclusion The present synthetic method is simple to perform and can be wddely used; meanwhile, the protective base can be easily removed. The target glyco amino acid is suitable for synthesis of various glycopeptides.
