The synthesis and solvolysis of some fully acetylated glycopyranosylulose chlorides

27Citations
Citations of this article
5Readers
Mendeley users who have this article in their library.
Get full text

Abstract

Several partially acetylated aldopyranosyl chlorides with an unprotected hydroxyl group at C-2 have been synthesised and some have been oxidised with ruthenium tetraoxide. In this way, fully acetylated pyranosylulose chlorides having the α-D-arabino-hexo, α-D-lyxo-hexo, and β-L-erythro-pento structures have been prepared. Their rates of methanolysis have been determined. Key intermediates in the synthetic sequences were the per-O-acetyl-2-O-trichloroacetylglycopyranosyl chlorides, of which the α- and β-D-galacto, α- and β-L-arabino, and α and β-D-xylo compounds were hitherto unknown. The β-D-xylo derivative exists in the conformation in which all the ring substituents are axially disposed, whereas the α-L-arabino compound is a rare example of an acylated pentopyranosyl chloride that adopts, preponderantly, a chair conformation that places the halogen in an equatorial orientation. © 1973.

Cite

CITATION STYLE

APA

Collins, P. M., Overend, W. G., & Rayner, B. A. (1973). The synthesis and solvolysis of some fully acetylated glycopyranosylulose chlorides. Carbohydrate Research, 31(1), 1–16. https://doi.org/10.1016/S0008-6215(00)82312-5

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free