Synthesis 2014; 46(09): 1185-1190
DOI: 10.1055/s-0033-1340851
paper
© Georg Thieme Verlag Stuttgart · New York

A Carbohydrate-Based Julia–Kocienski Reagent for Syntheses of Chain-Extended and C-Linked Saccharides

James A. Bull
Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany   Fax: +49(6131)3924786   Email: hokunz@uni-mainz.de
,
Horst Kunz*
Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany   Fax: +49(6131)3924786   Email: hokunz@uni-mainz.de
› Author Affiliations
Further Information

Publication History

Received: 11 December 2013

Accepted after revision: 03 February 2014

Publication Date:
18 February 2014 (online)

Abstract

The carbohydrate-derived Julia–Kocienski reagent 2-{[(3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methylsulfonyl}-1,3-benzothiazole (6) was prepared from d-ribose and investigated in the eponymous olefination. The base-promoted generation of the Julia anion induced a rearrangement­ to the corresponding l-lyxose epimer 2-{[(3aS,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methylsulfonyl}-1,3-benzothiazole (12), which reacted readily with aldehydes and with a gluconolactone. The latter reaction furnished an exo-glycal-linked C-diglycoside.

Supporting Information

 
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