ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A synthesis of 1,2-cis-configurated, non-isosteric phosphonate analogues of aldose-1-phosphates is described. Treatment of 1-O-acyl-glycoses 1, 7, 13, and 19 with trialkyl phosphite in the presence of trimethylsilyl trifluoromethanesulfonate gave the 1,2-cis-configurated glycosylphosphonates 2, 4, 8, 10, 14, 16, 20, and 22 as the major anomers and the 1,2-trans-configurated glycosylphosphonates 3, 5, 9, 11, 15, 17, 21, and 23 as the minor anomers. The 1,2-cis-configurated phosphonates 4, 10, 16, and 22 were deprotected to give the (β-D-glucopyranosyl)phosphonate 6, the (β-D-mannopyranosyl)phosphonate 12, the (β-D-ribofuranosyl)phosphonate 18, and the (β-D-arabinofuranosyl)phosphonate 24, respectively, in high yields. The preferred formation of 1,2-cis-configurated phosphonates is explained by postulating an equilibrium between the anomeric phosphonium-salt intermediates (such as 25 and 26) and a stabilization of the cis-configurated salts through formation of a pentacoordinated species (such as 28).
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19860690105
