Issue 4, 1969
From the journal:

Journal of the Chemical Society C: Organic

Unsaturated carbohydrates. Part IX. Synthesis of 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides from tri-O-acetyl-D-glucal

R. J. Ferrier  and  N. Prasad  

Abstract

Tri-O-acetyl-D-glucal undergoes complete reaction with alcohols in benzene solution in the presence of boron trifluoride to give 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosides. The α-anomers predominate (ca. 90%), and the method can be used to prepare the known crystalline ethyl α-glucoside easily and in greatly improved yield. Other alkyl glycosides have been prepared similarly, and the procedure has afforded means of obtaining the cholesteryl analogue and the disaccharide derivative 6-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose. Tri-O-acetyl-D-glucal again gave the 2,3-unsaturated glycosides on treatment with acetals in the presence of boron trifluoride; no evidence was obtained for the formation of branched-chain products produced by additions to the double bond.

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/J39690000570
Article type
Paper

J. Chem. Soc. C, 1969, 570-575

Permissions

Request permissions

Unsaturated carbohydrates. Part IX. Synthesis of 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides from tri-O-acetyl-D-glucal

R. J. Ferrier and N. Prasad, J. Chem. Soc. C, 1969, 570 DOI: 10.1039/J39690000570

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements