What question did this study set out to answer?

The research targets the regio- and stereoselective synthesis of sulfone sugars mediated by SnCl4.

January 23, 2026

Regio- and Stereoselective Synthesis of 1-/3-Sulfone Sugars Controlled by the Amount of SnCl 4

YXYimin XiangChina Three Gorges University JXJing XuChina Three Gorges University TXTao XiongChina Three Gorges University

Key Points

The research targets the regio- and stereoselective synthesis of sulfone sugars mediated by SnCl4.
Utilized SnCl4 for regioselective sulfonylation of glycal donors with sulfinic acids.
Conducted mechanistic studies to understand the activation of C3 leaving groups.
Explored the synthesis of 1-sulfone and 3-sulfone sugars by varying SnCl4 concentrations.
1-sulfone sugars obtained with 0-10 mol % SnCl4, while 3-sulfone sugars require 1 equivalent of SnCl4.
Broad substrate scope demonstrated strong regio- and stereoselectivity in reactions.
Findings suggest the potential for late-stage modification of natural products.

Abstract

A SnCl4-mediated regioselective sulfonylation of glycal donors with sulfinic acids enables stereodivergent synthesis of 1-sulfone sugars (0-10 mol % SnCl4) or 3-sulfone sugars (1 equiv of SnCl4), respectively. Mechanistic studies reveal that sulfinic acid can activate the C3 leaving group alone to form sulfone glycosides, while excess SnCl4 promotes the 1,3-shift to afford 3-sulfone sugars. The protocol exhibits broad substrate scope, including late-stage modification of natural products, with excellent regio-/stereoselectivity.

اسأل الذكاء الاصطناعي

Bookmark

View Full Paper