Studies on the synthesis of apoptolidin A. 2. Synthesis of the disaccharide unit

Masaki Handa; William J Smith 3rd; William R Roush

doi:10.1021/jo7022526

Studies on the synthesis of apoptolidin A. 2. Synthesis of the disaccharide unit

J Org Chem. 2008 Feb 1;73(3):1036-9. doi: 10.1021/jo7022526. Epub 2007 Dec 29.

Authors

Masaki Handa¹, William J Smith 3rd, William R Roush

Affiliation

¹ Department of Chemistry, Scripps-Florida, Jupiter, Florida 33458, USA.

PMID: 18163646
DOI: 10.1021/jo7022526

Abstract

Disaccharide 3 correspoinding to the disaccharide unit of apoptolidin A has been synthesized via the regio- and stereoselective TBS-OTf-promoted beta-glycosidation reaction of 2,6-dideoxy-2-iodo-beta-glucopyranosyl acetate (5) and p-methoxybenzyl 2,6-dideoxy-2-iodo-3-C-methyl-alpha-mannopyranoside (11).

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Disaccharides / chemistry*
Glycosides / chemistry
Macrolides / chemical synthesis*
Macrolides / chemistry
Molecular Structure
Pyrones / chemical synthesis*
Pyrones / chemistry
Stereoisomerism

Substances

Disaccharides
Glycosides
Macrolides
Pyrones
apoptolidin A

Grants and funding

GM038436/GM/NIGMS NIH HHS/United States