NEW ASPECT OF THERMODYNAMIC STABILITY OF 3-C-NITRO-D-GLYCAL DERIVATIVES

Authors
SETA A NAGANO C ITO S TOKUDA K TAMURA T KAMITANI T SAKAKIBARA T
Citation
A. Seta et al., NEW ASPECT OF THERMODYNAMIC STABILITY OF 3-C-NITRO-D-GLYCAL DERIVATIVES, Tetrahedron letters, 39(7), 1998, pp. 591-594
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
7
Year of publication
1998
Pages
591 - 594
Database
ISI
SICI code
0040-4039(1998)39:7<591:NAOTSO>2.0.ZU;2-I
Abstract
Thermodynamic stability of 3-C-nitro-D-glucal and -D-allal derivatives as well as the corresponding 5 alpha-carba sugars was reproduced by a b initio (6-31G) calculations. The calculations also predicted that 3 -C-nitro-D-gulal should be more stable than its 3-epimer in spite of s trong bias for a nitro group at C-3 to occupy the equatorial position. This prediction was experimentally proved (C) 1998 Elsevier Science L td. All rights reserved.