RING-OPENING REACTIONS OF BENZYL 2,3-ANHYDRO-ALPHA-D-RIBOPYRANOSIDE WITH NUCLEOPHILES

Authors
VASUDEVA PK NAGARAJAN M
Citation
Pk. Vasudeva et M. Nagarajan, RING-OPENING REACTIONS OF BENZYL 2,3-ANHYDRO-ALPHA-D-RIBOPYRANOSIDE WITH NUCLEOPHILES, Tetrahedron, 52(15), 1996, pp. 5607-5616
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
15
Year of publication
1996
Pages
5607 - 5616
Database
ISI
SICI code
0040-4020(1996)52:15<5607:RROB2W>2.0.ZU;2-W
Abstract
Nucleophilic ring opening reactions of benzyl 2,3 anhydro-alpha-D-ribo pyranoside with different nucleophiles resulted in exclusive formation of 3-substituted-3-deoxyxylose derivatives in good yields: The regioc hemical outcome of the ring opening reaction is controlled by a polar repulsive interaction between the entering nucleophile and the pyranos e oxygen lone pair of electrons. Copyright (C) 1996 Elsevier Science L td