An efficient and versatile synthesis of apiose and some C-1-aldehyde- and/or 2,3- O-protected derivatives

The synthesis of 2,3- O-isopropylidene-β- d-apiofuranose (58% overall yield) from l-arabinose via 3- C-(hydroxymethyl)-2,3- O-isopropylidene- d- glycero-tetrose diethyl dithioacetal is reported. Starting from l-arabinose an alternative precursor of d-apiose, 3- C-(hydroxymethyl)-2,3- O-isopropyliden...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2002-07, Vol.43 (31), p.5405-5406
Main Authors: Koóš, Miroslav, Mičová, Júlia, Steiner, Bohumil, Alföldi, Juraj
Format: Article
Language:English
Subjects:
acetals
aldol-Cannizzaro reaction
dithioacetals
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The synthesis of 2,3- O-isopropylidene-β- d-apiofuranose (58% overall yield) from l-arabinose via 3- C-(hydroxymethyl)-2,3- O-isopropylidene- d- glycero-tetrose diethyl dithioacetal is reported. Starting from l-arabinose an alternative precursor of d-apiose, 3- C-(hydroxymethyl)-2,3- O-isopropylidene- d- glycero-tetrose dimethyl acetal, was prepared from 2,3- O-isopropylidene- l- threo-tetrodialdose dimethyl acetal and formaldehyde by the aldol-Cannizzaro reaction. Unprotected d-apiose is accessible from both precursors on acid hydrolysis. A stepwise synthesis of d-apiose and some protected derivatives is described starting from l-arabinose.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01084-5