7-Azido-N,N-diethyl-4,5-O-isopropyl-idene-4-C-methyl-3,6-anhydro-7-de-oxy-d-glycero-d-manno-heptonamide.

Jenkinson SF, Wang C, Pino-González M-S, Fleet GWJ, Watkin DJ

The reaction of 5-azido-5-de-oxy-2,3-O-isopropyl-idene-2-C-methyl-d-ribose with N,N-diethyl-2-(dimethyl-sulfuranyl-idene)acetamide gave the title compound, C(15)H(26)N(4)O(5), as the major product arising from initial formation of an epoxide which was subsequently opened by intra-molecular attack of the free 4-hydroxyl group. X-ray crystallography confirmed the relative stereochemistry of the title compound and the absolute configuration was determined by the use of d-ribose as the starting material. The crystal structure contains chains of mol-ecules running parallel to the a axis, being linked by weak bifurcated O-H⋯(N,N) hydrogen bonds.