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6-Azido-3-O-benzyl-6-de-oxy-N,N-diethyl-1,2-O-isopropyl-idene-d-glycero-?-d-gluco-heptofuran-uronamide.

ABSTRACT: Reaction of 3-O-benzyl-1,2-O-isopropyl-idene-?-xylo-pentodialdo-1,4-furan-ose with N,N-diethyl-2-(dimethyl-sulfuranil-idene)acetamide gave stereoselectively an ep-oxy-amide, which was regioselectively opened by NaN(3) in dimethyl formamide to give the title compound, C(21)H(30)N(4)O(6). X-ray crystallography confirmed the relative stereochemistry of the title compound and the absolute configuration was determined by the use of d-glucose as the starting material. There are two mol-ecules in the asymmetric unit (Z' = 2). The crystal structure consists of two types of chains of O-H?O hydrogen-bonded mol-ecules running parallel to the b axis, with each mol-ecule acting as a donor and acceptor of one hydrogen bond.

SUBMITTER: Jenkinson SF 

PROVIDER: S-EPMC3050294 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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6-Azido-3-O-benzyl-6-de-oxy-N,N-diethyl-1,2-O-isopropyl-idene-d-glycero-α-d-gluco-heptofuran-uronamide.

Jenkinson S F SF   Oña N N   Romero A A   Fleet G W J GW   Thompson A L AL   Pino-González M S MS  

Acta crystallographica. Section E, Structure reports online 20101204 Pt 1

Reaction of 3-O-benzyl-1,2-O-isopropyl-idene-α-xylo-pentodialdo-1,4-furan-ose with N,N-diethyl-2-(dimethyl-sulfuranil-idene)acetamide gave stereoselectively an ep-oxy-amide, which was regioselectively opened by NaN(3) in dimethyl formamide to give the title compound, C(21)H(30)N(4)O(6). X-ray crystallography confirmed the relative stereochemistry of the title compound and the absolute configuration was determined by the use of d-glucose as the starting material. There are two mol-ecules in the a  ...[more]

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