Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals

The Journal of Organic Chemistry
Aditi AgarwalYashwant D Vankar

Abstract

Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good alpha selectivity. Primary, secondary, and allylic alcohols, phenols, and thiols react with 3,4,6-tri-O-acetyl glucal with equal ease. In addition to this, a chiral furan diol is obtained from unprotected D-glucal or D-galactal in good yields.

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Citations

Apr 26, 2013·Organic Letters·Hans A V KistemakerDmitri V Filippov
Oct 30, 2007·The Journal of Antibiotics·Maciej CierpuchaJolanta Solecka
Aug 27, 2015·Organic Letters·Hans A V KistemakerDmitri V Filippov
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Jul 4, 2018·Chemical Reviews·Michael Martin Nielsen, Christian Marcus Pedersen
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