Phosphorylation of N-glycosides derived from para-substituted aromatic amines

Abstract

New carbohydrate containing aminophosphoryl compounds were synthesized on the basis of glycosylamines. The reaction pathway suggested for addition of hydrophosphoryl compounds to N glycosides was confirmed.

Copper(I)-catalyzed hydrophosphination of styrenes

“…When the products were chromatographied on silica under nitrogen, a meaning loss of yield was observed (nearly 70% from the expected by NMR). 31 P assignments (d, ppm, H 3 PO 4 as reference): À41 (2) [32], À10.3 (3, isolated, see Supplementary material data) [25], þ31.7 (4, isolated, see Supplementary material data), þ18 (5) [33], þ26.8 (17, isolated, see Supplementary material data) [26], þ25.8 (PH 2 POOH) [17], À13.6 (Ph 2 P-PPh 2 ) [15]. For those experiments where iron or manganese catalysts were used, the mixture was passed through a pad of silica (AcOEt/ether (20 vol%) as eluent) after the reaction.…”