Transformations in carbohydrate chemistry part 1 - Synthesis of C-2 methylene O- and C-glycosides and sugar derived alpha-methylene-delta-valerolactones from C-2-acetoxymethyl glycals

Authors
Gupta, A Vankar, YD
Citation
A. Gupta et Yd. Vankar, Transformations in carbohydrate chemistry part 1 - Synthesis of C-2 methylene O- and C-glycosides and sugar derived alpha-methylene-delta-valerolactones from C-2-acetoxymethyl glycals, TETRAHEDRON, 56(43), 2000, pp. 8525-8531
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
43
Year of publication
2000
Pages
8525 - 8531
Database
ISI
SICI code
0040-4020(20001020)56:43<8525:TICCP1>2.0.ZU;2-P
Abstract
C-2-Methylene O- and C-glycosides are readily synthesized from C-2-acetoxym ethyl glycals using Nafion-H(R), montmorillonite K-10, LiClO4 (0.07 M) in d ichloromethane and Pd(PPh3)(4) as catalysts. Exclusive alpha or beta select ivities have been observed with various primary, secondary and tertiary alc ohols, phenols and diethyl malonate. Further, C-2-acetoxymethyl glycals are also converted into corresponding alpha -methylene-delta -valerolactones i n good yields in one step using m-CPBA in the presence of BF3. Et2O. (C) 20 00 Elsevier Science Ltd. All rights reserved.