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Synlett 2002(4): 0634-0636
DOI: 10.1055/s-2002-22716
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of N-Linked Glycosyl Asparagine Derivatives with Unprotected Sugar Components

Akihiro Ishiwataa, Maki Takatania, Yoshiaki Nakaharaa,b, Yukishige Ito*a
a RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan
b Department of Applied Biochemistry, Tokai University, Hiratsuka-shi, Kanagawa 259-1292 Japan
Fax: +81(48)4624680; e-Mail: yukito@postman.riken.go.jp;
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Publication History

Received 10 January 2001
Publication Date:
05 February 2007 (online)

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Abstract

A general methodology for the efficient formation of N-glycosidic linkage to asparagine (Asn), which, does not require the protection of sugar component hydroxyl groups is described. Aspartic acid fluoride was used in combination with N-allyloxycarbonyl (Alloc) glycosyl amines. Pd(0)-PhSiH3 mediated in situ Alloc removal-coupling was performed in aqueous solution dioxane to give Asn-linked carbohydrates in high yield.

Key words

asparagine - carbohydrate - aspartic acid fluoride - glycosylamine - allyl carbamate