New accesses to l-iduronyl synthons

(PhS) 3CLi adds with a total l- ido selectivity onto 3- O-benzyl-1,2- O-isopropylidene-α- d -xylo-dialdose 2, opening the way to the most efficient preparation of 1,2,4-tri- O-acetyl-3- O-benzyl- l-iduronyl synthon 8. Alternatively, in view of combinatorial syntheses, aldehyde 2 allows a good access...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 3; pp. 307 - 311
Main Authors Lubineau, A, Gavard, O, Alais, J, Bonnaffé, D
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.01.2000
Elsevier
Subjects
Chemistry
Chemistry, Organic
glycosaminoglycans
heparin
l-idose
l-iduronic acid
organometallic
oxidation
Physical Sciences
Science & Technology
glycosaminoglycans
heparin
oxidation
l-idose
organometallic
l-iduronic acid
CONVENIENT SYNTHESIS
L-iduronic acid
BINDING DOMAIN
L-idose
Online AccessGet full text

Cover

More Information
Summary:(PhS) 3CLi adds with a total l- ido selectivity onto 3- O-benzyl-1,2- O-isopropylidene-α- d -xylo-dialdose 2, opening the way to the most efficient preparation of 1,2,4-tri- O-acetyl-3- O-benzyl- l-iduronyl synthon 8. Alternatively, in view of combinatorial syntheses, aldehyde 2 allows a good access to vinylic l- ido and d- gluco synthons which may be converted into uronic acid by a sequence involving a new aldehyde oxidation by m-CPBA in aqueous solution.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)02080-8