Rare and complex saccharides from D-galactose and other milk-derived carbohydrates. Part 12 - A new highly diastereoselective synthesis of epi-inositol from D-galactose

Authors
Pistara, V Barili, PL Catelani, G Corsaro, A D'Andrea, F Fisichella, S
Citation
V. Pistara et al., Rare and complex saccharides from D-galactose and other milk-derived carbohydrates. Part 12 - A new highly diastereoselective synthesis of epi-inositol from D-galactose, TETRAHEDR L, 41(17), 2000, pp. 3253-3256
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
17
Year of publication
2000
Pages
3253 - 3256
Database
ISI
SICI code
0040-4039(20000422)41:17<3253:RACSFD>2.0.ZU;2-W
Abstract
The inosose derivative 3 was obtained with high stereoselectivity by intram olecular aldol condensation of the aldohexos-5-ulose derivative 2, and it w as selectively reduced and debenzylated to give epi-inositol in high yield. The stereochemistry and the preferred conformations of compounds 3-7 were determined through 1D and 2D NMR experiments. (C) 2000 Published by Elsevie r Science Ltd. All rights reserved.