Issue 53, 2018, Issue in Progress

Highly reactive 2-deoxy-2-iodo-d-allo and d-gulo pyranosyl sulfoxide donors ensure β-stereoselective glycosylations with steroidal aglycones

Abstract

The preparation of well-defined D-xylo and D-ribo glycosides represents a synthetic challenge due to the limited configurational availability of starting materials and the laborious synthesis of homogeneous 2-deoxy-β-glycosidic linkages, in particular that of the sugar-steroid motif, which represents the “stereoselective determining step” of the overall synthesis. Herein we describe the use of 2-deoxy-2-iodo-glycopyranosyl sulfoxides accessible from widely available D-xylose and D-ribose monosaccharides as privileged glycosyl donors that permit activation at very low temperature. This ensures a precise kinetic control for a complete 1,2-trans stereoselective glycosylation of particularly challenging steroidal aglycones.

Graphical abstract: Highly reactive 2-deoxy-2-iodo-d-allo and d-gulo pyranosyl sulfoxide donors ensure β-stereoselective glycosylations with steroidal aglycones

Supplementary files

Article information

Article type
Paper
Submitted
06 Aug 2018
Accepted
11 Aug 2018
First published
24 Aug 2018
This article is Open Access
Creative Commons BY license

RSC Adv., 2018,8, 30076-30079

Highly reactive 2-deoxy-2-iodo-D-allo and D-gulo pyranosyl sulfoxide donors ensure β-stereoselective glycosylations with steroidal aglycones

J. Mestre, D. Collado, D. Benito-Alifonso, M. A. Rodríguez, M. I. Matheu, Y. Díaz, S. Castillón and O. Boutureira, RSC Adv., 2018, 8, 30076 DOI: 10.1039/C8RA06619A

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