Issue 56, 2014
From the journal:

RSC Advances

Synthesis of monoglycosides, bisglycosides and open-chain ketoacetals from sugar derived exocyclic enol ethers†

Soumendra Nath Das,a   Praveen Krishna Kb  and  Sukhendu Bikas Mandal*a  

* Corresponding authors

a Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700 032, India
E-mail: sbmandal@iicb.res.in

b National Institute of Pharmaceutical Education and Research, 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700 032, India

Abstract

Under acidic conditions, the reaction of pent-4-enofuranosides with various nucleophiles of mostly alcohol origin furnished bisglycosylated products along with open-chain ketoacetals and monoglycosylated products depending upon the reagents and reaction conditions. The reactions appear to proceed via nucleophilic attack at C-1 and/or C-4 of the reaction intermediates.

Graphical abstract: Synthesis of monoglycosides, bisglycosides and open-chain ketoacetals from sugar derived exocyclic enol ethers

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Article information

DOI
https://doi.org/10.1039/C4RA03340J
Article type
Paper
Submitted
13 Apr 2014
Accepted
23 Jun 2014
First published
23 Jun 2014

RSC Adv., 2014,4, 29542-29548

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Synthesis of monoglycosides, bisglycosides and open-chain ketoacetals from sugar derived exocyclic enol ethers

S. N. Das, P. K. K and S. B. Mandal, RSC Adv., 2014, 4, 29542 DOI: 10.1039/C4RA03340J

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