Total Syntheses of Carbohydrates, IV. 2-Deoxy-DL-, L- and D-erythro-pentoses and Related Sugars

Autor:	Sachiko Shioi, Mikio Shibuya, Gen Nakaminami, Yoko Sugiyama, Masazumi Nakagawa, Satoko Isemura
Rok vydání:	1972
Předmět:	chemistry.chemical_compound Potassium hydroxide Aqueous solution chemistry Yield (chemistry) Diastereomer Sodium azide Organic chemistry Stereoselectivity General Chemistry Borane Ion-exchange resin Medicinal chemistry
Zdroj:	Bulletin of the Chemical Society of Japan. 45:2624-2634
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.45.2624
Popis:	5-Bromo-2,5-dideoxy-threo-pentono-γ-lactone (III) could be obtained stereoselectively from 3-hydroxy-4-pentenoic acid (I) by the reaction with N-bromosuccinimide in water. On successive treatment with an aqueous potassium hydroxide and an acid type cation exchange resin, bromolactone (III) gave stereoselectively 2-deoxy-erythro-pentono-γ-lactone (IV). Reduction of IV by means of bis(1,2-dimethylpropyl)borane afforded 2-deoxy-erythro-pentose (V). 3-Hydroxy-4-pentenoic acid (I) could be optically resolved. The (+)-acid yielded 2-deoxy-D-erythro-pentose (D-V) and the (−)-acid could be converted to 2-deoxy-L-erythro-pentose (L-V). 2,5-Dideoxy-threo-pentose (VIII) and 5-bromo-2,5-dideoxy-threo-pentose (IX) were obtained from bromo-lactone (III). Diethyl mercaptal of IX gave azido-compound (XI) in a low yield by the reaction with sodium azide. The conformation of γ-lactones (III, IV, and VII) and the mechanistic aspects of stereoselective reactions are discussed.
Databáze:	OpenAIRE
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