Can I read Formation and Equilibration of D-fructosides and 2-Thio-d-fructosides in Acidified Dimethyl Sulfoxide: Synthetic and Mechanistic Aspects on EtoBox?

Formation and Equilibration of D-fructosides and 2-Thio-d-fructosides in Acidified Dimethyl Sulfoxide: Synthetic and Mechanistic Aspects by Wayne Moody; Geoffrey N. Richards is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

What is Formation and Equilibration of D-fructosides and 2-Thio-d-fructosides in Acidified Dimethyl Sulfoxide: Synthetic and Mechanistic Aspects about?

A kinetic study of the reaction of ketoses and ketosides under catalysis with very dilute acid to produce the ketosyl carbonium ion is reported, and the subsequent reaction of this ion with alcohol and thiol nucleophiles has been studied. The relative reactivity of D-fructosides and 2-thio-D-fructosides is discussed, and some tentative conclusions have been reached on the mechanisms of their furanoside-pyranoside equilibration. The change in ring size in such systems probably proceeds via an anhydro-D-fructose intermediate, rather than an acyclic intermediate. The synthetic applications of the system have been explored, and it has been shown that both D-fructosides and 2-thio-D-fructosides may be synthesized in good yield. The D-fructofuranosides are best obtained from sucrose as the starting material, whereas the pyranosides are obtained from any readily available D-fructopyranoside (e.g., methyl /3) by use of the desired alcohol or thiol, only the p anomers being obtained. Three new 2-thio-D-fructosides are reported.

Who reads Formation and Equilibration of D-fructosides and 2-Thio-d-fructosides in Acidified Dimethyl Sulfoxide: Synthetic and Mechanistic Aspects?

Author

Wayne Moody; Geoffrey N. Richards

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1983

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)