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Updated: Aug 21, 2026

Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
Published on: February 17, 2017
Synthesis of thioglycoside-based UDP-sugar analogues
Xiangming Zhu1, Florian Stolz, Richard R Schmidt
1Fachbereich Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany.
Abstract:
Arbuzov reaction of O-acetyl-protected glycosylthiomethyl chlorides with triethyl phosphite and then phosphonate ethyl ester cleavage with trimethylsilyl bromide afforded glycosylthiomethyl phosphonates 13, 18, 22, and 26. These intermediates could be readily transformed into the O-deprotected phosphonates 7-10 and into title compounds 1-4. Similarly, sulfonomethyl phosphonate moieties containing UDP-sugar analogues 5 and 6 were obtained.
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