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翻訳と辞書　辞書検索 [ 開発暫定版 ] スポンサード リンク 3-Hydroxytetrahydrofuran ： ウィキペディア英語版 3-Hydroxytetrahydrofuran 3-Hydroxytetrahydrofuran (3-OH THF) is a colorless liquid with a normal boiling point of 179 °C and boiling at 88−89 °C at 17 mmHg, with density (1.087 g/cm3 at 19 °C). 3-OH THF is a useful pharmaceutical intermediate. The chiral (absolute configuration ''S'') version of this compound is an intermediate to launched retroviral drugs.〔Venkata Mandava, et al., “Preparation of fosamprenavir calcium” U.S. Pat. Appl., 20110224443 (2011)〕 == Synthesis == 3-Hydroxytetrahydrofuran was prepared in 1910 by Pariselle via cyclization and hydrolysis of 3,4-Dibromo-1-methoxybutane. Chiral 3-hydroxytetrahydrofuran (both (''S'') - and (''R'')-forms) has been synthesized in high enantiomeric purity from (''S'')- and (''R'')-1,2,4-butanetriol, respectively, obtained from chiral feedstocks. Thus, the chiral (''S'')-1,2,4-butanetriol intermediate was cyclized to chiral (''S'')-3-hydroxytetrahydrofuran in the presence of ''p''-toluenesulfonic acid (PTSA) catalyst at temperatures of 180−220 °C. Similarly, (''S'')-3-hydroxytetrahydrofuran was prepared in 95.8% optical purity from L-malic acid via an esterification-reduction-cyclodehydration sequence. 3-hydroxytetrahydrofuran has been synthesized via hydroboration of 2,3- and 2,5-dihydrofuran employing various borane reagents and chiral 3-hydroxytetrahydrofurans have also been prepared by catalytic asymmetric hydroboration of 2,3- and 2,5-dihydrofurans with a borane in the presence of a homogeneous chiral platinum complex, followed by oxidation.〔Anita Schnyder, et al., “Preparation of optically active 3-hydroxytetrahydrofurans by catalytic asymmetric hydroboration of dihydrofurans” Ger. Offen., 19807330 (1998)〕 Racemic 3-hydroxytetrahydrofuran may be prepared in analogous fashion from racemic butanetriol, employing PTSA catalyst for the dehydrocyclization. Alternatively, 1,2,4-butanetriol may be converted to 3-hydroxytetrahydrofuran by treating with ethylene carbonate, followed by pyrolysis of the resulting carbonate ester. 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「3-Hydroxytetrahydrofuran」の詳細全文を読む スポンサード リンク 翻訳と辞書 : 翻訳のためのインターネットリソース Copyright(C) kotoba.ne.jp 1997-2016. All Rights Reserved.