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Synthesis 2004(10): 1641-1647  
DOI: 10.1055/s-2004-829103
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Typical Glucuronide-Containing Saponin, 28-O-β-d-Glucopyranosyl Oleanate 3-O-β-d-Galactopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→3)]-β-d-glucuronopyranoside

Wenjie Penga, Xiuwen Hana, Biao Yu*b
a State Key Laboratory of Catalyst, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. of China
b State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
e-Mail: byu@mail.sioc.ac.cn;
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Publication History

Received 27 February 2004
Publication Date:
16 June 2004 (online)

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Abstract

28-O-β-d-Glucopyranosyl oleanate 3-O-β-d-galactopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→3)]-β-d-glucuronopyranoside (1), a structurally typical glucuronide-containing triterpene saponin isolated from Aralia dasyphylla, was concisely synthesized in linear nine steps and 26% overall yield. The key features of the synthesis are: (1) attachment of the 28-glucosyl ester ahead of assembly of the 3-O-sugar chain; (2) elaboration of the glucuronide residue at a later stage via the TEMPO-mediated selective oxidation; (3) installation of 2-(azidomethyl)benzoyl group as a benzoylic neighboring participating group which is selectively removed afterwards for synthesis of the 1→2 sugar linkage.

Keywords

triterpene saponin - glucuronide - synthesis - glycosylation - oxidation