Reaction of 4,6-O-benzylideneglycals with benzoic acid, triphenyl-phosphine, and diethyl azodicarboxylate and of the products with sodium methoxide. X-Ray structure of 1-O-benzoyl-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranose, C21H22O6

Autor:	Jill Trotter, Bruce E. Davison, Kim Henrick, Robert W. Irvine, R. D. Guthrie
Rok vydání:	1981
Předmět:	Diethyl azodicarboxylate chemistry.chemical_compound Chemistry X-ray Organic chemistry Orthorhombic crystal system Triphenylphosphine Sodium methoxide Medicinal chemistry Derivative (chemistry) Phosphine Benzoic acid
Zdroj:	J. Chem. Soc., Perkin Trans. 2. :468-472
ISSN:	1364-5471 0300-9580
DOI:	10.1039/p29810000468
Popis:	Reaction of 4,6-O-benzylidene-D-allal with benzoic acid, triphenylphosphine, and diethyl azodicarboxylate gave a mixture of 1-O-benzoyl-4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranose (3) as the major product together with its β-anomer (4) and 3-O-benzoyl-4,6-O-benzylidene-D-glucal (5). Debenzoylation led to a mixture of the 4,6-O-benzylidene-D-glucal, 4,6-O-benzylidene-2-deoxy-3-O-methyl-D-arabino- and -D-ribo-hexopyranose. The structure of the arabino-isomer (6) was established by X-ray analysis of its 1-O-benzoyl derivative. Crystals are orthorhombic, space group P212121, a= 21.789(2), b= 14.772(3), c= 5.925(2)A. The structure was solved by direct methods and refined to R 0.095.
Databáze:	OpenAIRE
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