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Updated: Mar 23, 2026

Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
Published on: February 17, 2017
First total synthesis of trehalose containing tetrasaccharides from Mycobacterium smegmatis
Manishkumar A Chaube1, Vikram A Sarpe1, Santanu Jana1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India. suvarn@chem.iitb.ac.in.
Abstract:
Total synthesis of three important trehalose containing tetrasaccharides isolated from Mycobacterium smegmatis is reported for the first time, using regioselective opening of benzylidene acetals and stereoselective glycosylations as key steps. The 1,2-cis stereoselectivity in the glycosylation reactions was achieved using anchimeric assistance from a remote participating group, steric effects and solvent participation. The synthetic strategy can also be utilized for the assembly of structurally related oligosaccharides from M. tuberculosis.
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