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Updated: Aug 22, 2025

Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
Published on: February 17, 2017
Protecting group enabled stereocontrolled approach for rare-sugars talose/gulose via dual-ruthenium catalysis
Manoj Kumar1, Nitin Kumar1, Aakanksha Gurawa1
1Carbohydrate Chemistry Research Laboratory (CCRL), Department of Chemistry, Malaviya National Institute of Technology (MNIT), Jaipur, 302017, India.
Abstract:
We herein report a convenient and highly stereocontrolled approach for rare and vital ᴅ-talo and ᴅ-gulo sugars directly from economical ᴅ-galactal through dual ruthenium-catalysis. The stereo-divergent strategy involves Ru(III)Cl3-catalyzed Ferrier glycosylation of ᴅ-galactal to give 2,3-unsaturated ᴅ-galactopyranoside, further selective functionalization of C-4 and C-6 position with diverse protecting groups and dihydroxylation with Ru(VIII)O4 generated in situ providing access to talo/gulo isomers. The α-anomeric stereoselectivity and syn-diastereoselectivity in glycosylation-dihydroxylation steps have been predominantly achieved by judicious selection of stereoelectronically diverse protecting groups. The synthetic utility of the dual-ruthenium catalysis was demonstrated for efficiently assembling the ᴅ-talose and/or ᴅ-gulose sugars in natural products and bioactive scaffolds.
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