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(S)-3-Dimethyl-amino-2-{(4S,5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxy-propanoic acid.

ABSTRACT: The Kiliani reaction on 1-de-oxy-(N,N-dimethyl-amino)-d-fructose, itself readily available from reaction of dimethyl-amine and d-glucose, proceeded to give access to the title ?-sugar amino acid, C(15)H(27)NO(7). X-ray crystallography determined the stereochemistry at the newly formed chiral center. There are two mol-ecules in the asymmetric unit; they are related by a pseudo-twofold rotation axis and have very similar geometries, differing only in the conformation of one of the acetonide rings. All the acetonide rings adopt envelope conformations; the flap atom is oxygen in three of the rings, but carbon in one of them. There are two strong hydrogen bonds between the two independent mol-ecules, and further weak hydrogen bonds link the mol-ecules to form infinite chains running parallel to the a axis.

SUBMITTER: Jenkinson SF 

PROVIDER: S-EPMC2915345 | biostudies-literature | 2007 Dec

REPOSITORIES: biostudies-literature

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(S)-3-Dimethyl-amino-2-{(4S,5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxy-propanoic acid.

Jenkinson Sarah F SF   Hotchkiss David J DJ   Cowley Andrew R AR   Fleet George W J GW   Watkin David J DJ  

Acta crystallographica. Section E, Structure reports online 20071218 Pt 1

The Kiliani reaction on 1-de-oxy-(N,N-dimethyl-amino)-d-fructose, itself readily available from reaction of dimethyl-amine and d-glucose, proceeded to give access to the title β-sugar amino acid, C(15)H(27)NO(7). X-ray crystallography determined the stereochemistry at the newly formed chiral center. There are two mol-ecules in the asymmetric unit; they are related by a pseudo-twofold rotation axis and have very similar geometries, differing only in the conformation of one of the acetonide rings.  ...[more]

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