Convenient Synthesis of 1α,25-Dihydroxyvitamin D3from Vitamin D2

Autor:	Minokazu Takahashi, Yasumasa Sakakibara
Rok vydání:	1994
Předmět:	Vitamin chemistry.chemical_compound Hydrolysis chemistry 1α 25 dihydroxyvitamin d3 Organic chemistry Butane Alcohol General Chemistry
Zdroj:	Bulletin of the Chemical Society of Japan. 67:2494-2499
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.67.2494
Popis:	(1S,6R)-1-Acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclovitamin D2 (7) was synthesized from vitamin D2 by five steps. The new compound 7 was ozonized regioselectively and subsequently reduced, leading to (7E)-(1S,3S,5R,6R)-1-acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclo-9,10-seco-23,24-dinor-7,10(19)-choladien-22-ol (11). The alcohol 11 obtained as a key intermediate was tosylated, iodinated, and coupled with 2-methyl-4-phenylsulfonyl-2-(tetrahydropyranyloxy)butane to give (1S,6R)-1-hydroxy-6-(1,3-benzodithiol-2-yloxy)-23-phenylsulfonyl-25-tetrahydropyranyloxy-3,5-cyclovitamin D3 (16). By desulfonylation and hydrolysis of the compound 16 1α,25-dihydoxyvitamin D3 was obtained selectively.
Databáze:	OpenAIRE
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