Facile synthesis of chiral N-glycosylated amino acids

Five designed chiral glycosylated amino acids have been synthesized for the first time by coupling of 1,3,4,6-tetra- O -acetyl-β- D -glucosamine sulfate ( 2 ), previously prepared by direct acetylation of D -glucosamine hydrochloride with acetic anhydride, with chiral Fmoc-protected amino acids and...

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Bibliographic Details
Published in:Research on chemical intermediates 2010-04, Vol.36 (3), p.237-243
Main Authors: Wang, Lin Fa, Kong, Ling Qiang, Fan, Li, Yang, Da Cheng
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Chemistry and Materials Science
Inorganic Chemistry
Physical Chemistry
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Summary:Five designed chiral glycosylated amino acids have been synthesized for the first time by coupling of 1,3,4,6-tetra- O -acetyl-β- D -glucosamine sulfate ( 2 ), previously prepared by direct acetylation of D -glucosamine hydrochloride with acetic anhydride, with chiral Fmoc-protected amino acids and DIC, HOBt, and DIEA under mild conditions. The structures of these new compounds were characterized by IR, 1 H NMR, and 13 C NMR spectroscopy and ESI MS.
ISSN:0922-6168
1568-5675
DOI:10.1007/s11164-010-0133-6