The azidonitration of tri-O-acetyl-D-galactal
- 15 May 1979
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 57 (10) , 1244-1251
- https://doi.org/10.1139/v79-203
Abstract
Reaction of 3,4,6-tri-O-acetyl-D-galactal with excess ceric ammonium nitrate and sodium azide in acetonitrile produced 2-azido-1-nitrate addition products (53% .beta.-galacto, 22% .alpha.-galacto and 8% .alpha.-talo) and N-acetyl-3,4,6-tri-O-acetyl-2-acido-2-deoxy-.alpha.-D-galactopyranosylamine was formed, on hydrolysis, in 10% yield. The reaction product provides a convenient source of D-galactosamine and 3,4,6-tri-O-acetyl-2-acido-2-deoxy-.alpha.-D-galactopyranosyl halides. The crystalline .beta.-chloride is reported. The use of these glycosyl halides as reactants for the preparation of 2-acido-2-deoxy-.alpha. and -.beta.-D-galactopyranosides under conditions promoted by both mercuric cyanide and silver salts are reported.This publication has 3 references indexed in Scilit:
- A synthesis of 3-O-(2-Acetamido-2-deoxy-α-D-galactopyranosyl)-D-galactopyranose and 3-O-α-D-Galactopyranosyl-D-galactopyranoseAustralian Journal of Chemistry, 1978
- Synthesis of 2-amino-2-deoxy-D-talose and 2-amino-2-deoxy-D-galactoseCanadian Journal of Chemistry, 1968
- The synthesis of 2-amino-2-deoxyhexoses: D-glucosamine, D-mannosamine, D-galactosamine, and D-talosamineCanadian Journal of Chemistry, 1968