THE ALPHA AND BETA 1,3,4,6-TETRAACETYL-D-GLUCOPYRANOSES AND THEIR CHLOROACETYL DERIVATIVES
- 1 November 1953
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 31 (11), 1040-1047
- https://doi.org/10.1139/v53-136
Abstract
Reaction of 3,4,6-triacetyl-β-D-glucopyranosyl chloride with silver acetate in acetic acid gave 1,3,4,6-tetraacetyl-α-D-glucopyranose, m.p. 97–98 °C., [α]D + 145° (chloroform). 3,4,6,-Triacetyl-α-D-glucopyrartosyl chloride, m.p. 93–94 °C., [α]D + 185° (chloroform), prepared from the β-anomer by isomerization in acetone, with silver acetate in acetic acid gave 1,3,4,6-tetraacetyl-β-D-glucopyranose, m.p. 137–138 °C., [α]D + 26° (chloroform). The structures of these glucose tetraacetates were established by the interconversion of chloroacetyl derivatives.Keywords
This publication has 8 references indexed in Scilit:
- THE MECHANISMS OF GLUCOSE PENTAACETATE ANOMERIZATION AND LEVOGLUCOSAN FORMATIONCanadian Journal of Chemistry, 1952
- The Acid-catalyzed Anomerization of the D-Glucose Pentaacetates. A Kinetic Thermodynamic and Mechanistic Study1Journal of the American Chemical Society, 1951
- Mechanisms for the formation of acetylglycosides and orthoesters from acetylglycosyl halidesJournal of Research of the National Bureau of Standards, 1949
- The Role of Neighboring Groups in Replacement Reactions. XIII.1 General Theory of Neighboring Groups and ReactivityJournal of the American Chemical Society, 1948
- Glucoside und β‐1,3,4,6‐Tetraacetyl‐glucose aus Triacetyl‐glucosan‐αβHelvetica Chimica Acta, 1948
- Versuche zur Herstellung von 3,4-Diacetyl-d-chinovosan-??1,2? ??1,5?Helvetica Chimica Acta, 1947
- 2,3,4-Triacetyl-α-methylglucopyranoside-6-nitrate and 3,4,6-Triacetyl-β-methylglucopy-ranoside-2-nitrateJournal of the American Chemical Society, 1944
- A NOTE ON THE ACTION OF SILVER SALTS OF ORGANIC ACIDS ON BROMOACETYL SUGARS. A NEW FORM OF TETRAACETYL l-RHAMNOSEPublished by Elsevier ,1939