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2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride-oxy-l-xylitol (N-benzyl-l-XYLNAc).

ABSTRACT: X-ray crystallography defines the relative configuration at the three-stereogenic centres in the title compound N-benzyl-l-XYLNAc, C(14)H(20)N(2)O(3). The five-membered pyrrolidine ring adopts an envelope conformation with the N atom lying out of the plane of the other four atoms. In the crystal structure, inter-molecular O-H?O, N-H?O and O-H?N hydrogen bonds link the mol-ecules into chains along [100]. The carbonyl group O atom acts as an acceptor for a bifurcated hydrogen bond. The absolute configuration is determined by the use of l-glucuronolactone as the starting material for the synthesis.

SUBMITTER: Jenkinson SF 

PROVIDER: S-EPMC2979175 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature

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2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride-oxy-l-xylitol (N-benzyl-l-XYLNAc).

Jenkinson Sarah F SF   Crabtree Elizabeth V EV   Glawar Andreas F G AF   Butters Terry D TD   Fleet George W J GW   Watkin David J DJ  

Acta crystallographica. Section E, Structure reports online 20100424 Pt 5

X-ray crystallography defines the relative configuration at the three-stereogenic centres in the title compound N-benzyl-l-XYLNAc, C(14)H(20)N(2)O(3). The five-membered pyrrolidine ring adopts an envelope conformation with the N atom lying out of the plane of the other four atoms. In the crystal structure, inter-molecular O-H⋯O, N-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules into chains along [100]. The carbonyl group O atom acts as an acceptor for a bifurcated hydrogen bond. The absolute co  ...[more]

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