Reaction of acetyl- and alkylideneglycosylamines with diphenylphosphinous acid

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

“…The addi tion of Ph 2 POH to anilides of protected monosaccharides has been described by us earlier 13 and it was shown that the process of phosphorylation occurred slowly, heating for 24-27 h in the presence of pyridine as the catalyst has been required.…”

“…Their struc tures were confirmed by the data from NMR spectroscopy ( 1 H, 13 C, and 31 P) and elemental analysis. In the 31 P NMR spectra of the compounds synthesized, two signals with virtually the same integral intensities or one broad signal in the region δ 30 were recorded.…”

“…In the crystal of compound 3 with a chiral center C (13), only (S) enantiomer is present. The furyl fragment is cis with respect to the phenyl ring C(7)-C (12) and trans with re spect to the ring C(1)-C(6) (Fig.…”

“…Despite the presence of appropriate proton acceptor in molecule 3, the NH group is not involved in the hydrogen bonding. According to the analysis of the crystal package of 3, the strongest intermolecular contact apparently is the trifur cate bond joining the O(1) atom with the H (19), H (2), and H (13), the latter being the most acidic among H at oms of the CH groups. It can be suggested that the H atom of the NH fragment is shielded by bulky substituents, viz., the furyl and the phenyl rings, which considerably hinders approach to it by the neighboring molecule.…”

“…A solu tion of compound5a-d, 6a,b (1 mmol)and Ph 2 POH (1 mmol) in chloroform (5 mL) was kept for 3-4 h at 25 °C under argon followed by concentration in vacuo, the residue was chromato graphed.1 C Diphenylphosphoryl 1 deoxy 1 (p toluidino) 2,3,4 tri O acetyl D xylitol (6a), R f 0.2, [α] D -5.5. 31 P NMR, δ: 30.1 (52%), 33.5 (48%) 13. C NMR, δ: H], 3 J H,P = 11.6 Hz), 8.00 (m, C(2´)H, C(6´)H, [C(2´)H, C(6´)H], 3 J H,P = 11.6 Hz).…”