2,4,6-Trichloro-1,3,5-triazine (TCT) mediated one-pot sequential functionalisation of glycosides for the generation of orthogonally protected monosaccharide building blocks

Orthogonally protected monosaccharide building blocks have been prepared using TCT in a one-pot multicomponent transformation. The process involves successive steps of arylidene acetalation, esterification and regioselective reductive acetal cleavage. High regioselectivity, scope for using a broad r...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-07, Vol.10 (28), p.5357-5360
Main Authors: Tatina, Madhubabu, Yousuf, Syed Khalid, Mukherjee, Debaraj
Format: Article
Language:English
Subjects:
Acetals - chemistry
Combinatorial Chemistry Techniques
Esterification
Glycosides - chemistry
Halogenation
Monosaccharides - chemical synthesis
Monosaccharides - chemistry
Stereoisomerism
Triazines - chemistry
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Summary:Orthogonally protected monosaccharide building blocks have been prepared using TCT in a one-pot multicomponent transformation. The process involves successive steps of arylidene acetalation, esterification and regioselective reductive acetal cleavage. High regioselectivity, scope for using a broad range of substrates, functional group tolerance, mild reaction conditions, easy handling process and wide application range are a few advantages of the current process.
ISSN:1477-0539
DOI:10.1039/c2ob25452b