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Large scale synthesis and regioselective protection schemes of ethyl 2-azido-2-deoxy-1-thio-α-d-cellobioside for preparation of heparin thiodisaccharide building blocks.

Authors :
Sheerin, Kevin
Guazzelli, Lorenzo
Oscarson, Stefan
Source :
Carbohydrate Research. Feb2017, Vol. 440, p16-31. 16p.
Publication Year :
2017

Abstract

Crystalline acetylated ethyl 2-azido-2-deoxy-1-thio-α- d -cellobioside has been prepared on a multigram scale from cellobiose in an overall yield of 23% with no chromatography required and converted after deacetylation into the 4′,6′- O -benzylidene and 4′,6′- O -benzylidene-6- O -TBDMS protected derivatives. Applying a number of regioselective benzylation methods on these gave access to a variety of regioselectively protected derivatives, both mono-ols (2′- and 3-OH), diols (2′,6-, 2′,3-, and 3,6-di-OH), and triols (2′,3,6- and 2′,3′,3-tri-OH). A number of these derivatives were further processed by benzoylation followed by removal or opening of the benzylidene acetal and selective oxidation of the exposed primary alcohol to give heparin building block intermediates comprising a range of possible sulfation patterns. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00086215
Volume :
440
Database :
Academic Search Index
Journal :
Carbohydrate Research
Publication Type :
Academic Journal
Accession number :
121453464
Full Text :
https://doi.org/10.1016/j.carres.2017.01.005