Dataset Information

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.

SUBMITTER: Mestre J

PROVIDER: S-EPMC9085402 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Publications

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

Mestre Jordi J Collado David D Benito-Alifonso David D Rodríguez Miguel A MA Matheu M Isabel MI Díaz Yolanda Y Castillón Sergio S Boutureira Omar O

RSC advances 20180824 53

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- ...[more]

PMID: 35546863

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Dataset Information

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

Publications

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

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