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Potential usefulness of sugar 1,2 thio ortho esters in iodonium-promoted glycosidation

✍ Scribed by H. M. Zuurmond; G. A. van der Marel; J. H. van Boom

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
406 KB
Volume
112
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Sugar 1,2 thio ortho esters can be condensed with terminal glycosyl acceptors using iodonium‐ion sources (IDCP and NIS/TfOH) as activators. IDCP‐ or NIS/TfOH‐assisted glycosidation of sugar 1,2 thio ortho esters with primary hydroxyl groups of “armed” or “disarmed” ethyl (phenyl) 1‐thioglycosides gave the respective disaccharides having 1,2 ortho ester or 1,2 trans interglycosidic linkages.

📜 SIMILAR VOLUMES

Iodonium ion promoted reactions at the a
Iodonium ion promoted reactions at the anomeric centre. II An efficient thioglycoside mediated approach toward the formation of 1,2-trans linked glycosides and glycosidic esters
✍ G.H. Veeneman; S.H. van Leeuwen; J.H. van Boom 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 271 KB

## N-iodosuccinimide (ND) in the presence of an organic acid was found to be effective for the activation of fully acylated thioglycosides leading to J&trans linked esters. On the other hand, NIS together with a catalytic amount of tri#luoromethanesu&onic acid proved to be very convenient for the ra