Synthesis of tri-O-acetyl-D-allal from levoglucosenone

Enrique D V Giordano; Agustina Frinchaboy; Alejandra G Suárez; Rolando A Spanevello

doi:10.1021/ol302061a

Synthesis of tri-O-acetyl-D-allal from levoglucosenone

Org Lett. 2012 Sep 7;14(17):4602-5. doi: 10.1021/ol302061a. Epub 2012 Aug 24.

Authors

Enrique D V Giordano¹, Agustina Frinchaboy, Alejandra G Suárez, Rolando A Spanevello

Affiliation

¹ Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, CONICET Suipacha 531, S2002LRK Rosario, Argentina.

PMID: 22920651
DOI: 10.1021/ol302061a

Abstract

Tri-O-acetyl-D-allal has been enantiospecifically synthesized in six steps from levoglucosenone in 55% overall yield. A key step in the synthesis is the anhydro bridge ring-opening with concomitant formation of a 1,3-oxathiolane-2-thione ring.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemistry*
Glucose / analogs & derivatives*
Glucose / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure

Substances

1,5-anhydro-2-deoxy-D-ribo-hex-1-enitol
Bridged Bicyclo Compounds, Heterocyclic
1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose
Glucose