Ready access to a branched Man5 oligosaccharide based on regioselective glycosylations of a mannose-tetraol with n-pentenyl orthoesters

Clara Uriel; Ana M. Gómez; J. Cristóbal López; Bert Fraser-Reid

doi:10.1039/C2OB26432C

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Organic & Biomolecular Chemistry

Issue 41, 2012

The international home of synthetic, physical and biomolecular organic chemistry.

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Ready access to a branched Man₅ oligosaccharide based on regioselective glycosylations of a mannose-tetraol with n-pentenyl orthoesters

Clara Uriel,^a Ana M. Gómez,*^a J. Cristóbal López*^a and Bert Fraser-Reid^b

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Instituto de Química Orgánica General (IQOG-CSIC), Juan de la Cierva 3, 28006 Madrid, Spain
E-mail: jc.lopez@csic.es ;
Fax: +34 91 5644853 ;
Tel: +34 91 5622900 Ext 320

Natural Products and Glycotechnology Research Institute Inc., (NPG), 595F, Weathersfield Road, Pittsboro, USA
E-mail: dglucose@aol.com ;
Fax: +1 9195427111 ;
Tel: +1 9195427111

Org. Biomol. Chem., 2012,10, 8361-8370

DOI: 10.1039/C2OB26432C
Received 21 Jul 2012, Accepted 24 Aug 2012
First published online 28 Aug 2012

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A branched Man₅ oligosaccharide has been synthesized by sequential regioselective glycosylations on a mannose-tetraol with n-pentenyl orthoester glycosyl-donors promoted by NIS/BF₃·Et₂O, in CH₂Cl₂. An extended n-pentenyl chain was incorporated into the tetraol acceptor to facilitate (a) the solubility of the starting tetraol in CH₂Cl₂, and (b) future manipulations at the reducing end of the Man₅ oligosaccharide.

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Ready access to a branched Man₅ oligosaccharide based on regioselective glycosylations of a mannose-tetraol with n-pentenyl orthoesters