Biocatalytic Preparation of (R) - (-) -4- (Phenylthio) -2-butanol and (R) - (-) -4- (Phenylsulfonyl) -2-butanol by the Sequential Use of Pichia farinosa and Rhodococcus rhodochrous

この論文にアクセスする

この論文をさがす

著者

抄録

Preparation of (<I>R</I>)-4-(phenylthio)-2-butanol and (<I>R</I>)-4-(phenylsulfonyl)-2-butanol has been established based on the sequential use of two biocatalysts. A <I>Pichia farinosa</I> IAM 4682 mediated reduction of 4-(phenylthio)-2-butanone afforded (<I>R</I>)-4-(phenylthio)-2-butanol (91%<I>e.e.</I>) in 90% yield. Contaminating (<I>S</I>)-enantiomer in the resulting product was selectively oxidized by <I>Rhodococcus rhodochrous</I> IFO15564 to leave pure (<I>R</I>)-enantiomer in 87% yield. From this product, highly enantiomerically pure (<I>R</I>)-4-(phenylsulfonyl)-2-butanol was obtained by hydrogen peroxide oxidation.

収録刊行物

  • Chemistry letters

    Chemistry letters 1996(3), 233-234, 1996-03-05

    The Chemical Society of Japan

参考文献:  37件中 1-37件 を表示

  • <no title>

    JACOBS H. K.

    Tetrahedron 48, 8891, 1992

    被引用文献1件

  • <no title>

    KOJIMA T.

    JP93, 111, 393

    被引用文献2件

  • <no title>

    KOJIMA T.

    JP93, 111, 392

    被引用文献2件

  • <no title>

    KOJIMA T.

    JP93, 117, 228

    被引用文献2件

  • <no title>

    TAKAGI N.

    JP95, 115, 992

    被引用文献2件

  • <no title>

    MIYAHARA O.

    JP92, 74, 161

    被引用文献2件

  • <no title>

    NAKATSUKA T.

    Chem. Soc., Chem. Commun. 1991, 662

    被引用文献1件

  • <no title>

    TAKEMURA T.

    Can. J. Chem. 68, 523, 1990

    被引用文献2件

  • <no title>

    FANTIN G.

    Tetrahedron : Asymmetry 2, 243, 1991

    被引用文献2件

  • <no title>

    FUJISAWA T.

    Tetrahedron Lett. 32, 399, 1991

    被引用文献4件

  • <no title>

    FUJISAWA T.

    Tetrahedron Lett. 32, 7055, 1991

    被引用文献2件

  • <no title>

    TAKABE K.

    Tetrahedron : Asymmetry 3, 1399, 1992

    被引用文献2件

  • <no title>

    AFONSO C. A. M.

    Tetrahedron 49, 4283, 1993

    被引用文献2件

  • <no title>

    NAKAMURA H.

    Tetrahedron Lett. 34, 8481, 1993

    被引用文献2件

  • <no title>

    SATO T.

    Biocatalysis 3, 1, 1990

    被引用文献2件

  • <no title>

    CSUK R.

    Chem. Rev. 91, 49, 1991

    被引用文献11件

  • <no title>

    GOPALAN A. S.

    Tetrahedron Lett. 31, 5575, 1990

    被引用文献2件

  • <no title>

    ROBIN S.

    Tetrahedron : Asymmetry 4, 239, 1993

    被引用文献2件

  • <no title>

    LIU H.

    J. Org. Chem. 60, 2023, 1995

    被引用文献2件

  • <no title>

    SUGAI T.

    Agric. Biol. Chem. 54, 1577, 1990

    被引用文献3件

  • <no title>

    SUGAI T.

    Tetrahedron 47, 7237, 1991

    被引用文献2件

  • <no title>

    MOCHIZUKI N.

    BioMed. Chem. 1, 71, 1993

    被引用文献3件

  • <no title>

    MIYAMOTO K.

    Biotechnol. Lett. 14, 363, 1992

    被引用文献2件

  • <no title>

    FANTIN G.

    Tetrahedron : Asymmetry 4, 1607, 1993

    被引用文献2件

  • <no title>

    FANTIN G.

    Tetrahedron Lett. 34, 883, 1993

    被引用文献3件

  • <no title>

    KOMETANI T.

    Chem. Lett. 1993, 2123

    被引用文献2件

  • <no title>

    FANTIN G.

    J. Org. Chem. 59, 924, 1994

    被引用文献2件

  • <no title>

    CARNELL A. J.

    Tetrahedron Lett. 35, 331, 1994

    被引用文献2件

  • <no title>

    NAKAMURA K.

    Tetrahedron Lett. 35, 4375, 1994

    被引用文献3件

  • <no title>

    DIETH S.

    Tetrahedron Lett. 36, 2243, 1995

    被引用文献2件

  • <no title>

    NAKAMURA K.

    Tetrahedron Lett. 36, 6263, 1995

    被引用文献3件

  • <no title>

    OHTA H.

    Chem. Lett. 1986, 581

    被引用文献2件

  • <no title>

    OHATA H.

    J. Org. Chem. 52, 2735, 1987

    被引用文献1件

  • <no title>

    ZELINSKI T.

    BioMed. Chem. 2, 421, 1994

    被引用文献2件

  • Microbial Asymmetric Reduction of (RS)-2-(4-Methoxyphenyl)-1,5-benzothiazepin-3,4(2H,5H)-dione, the Key Intermediate in the Synthesis of Diltiazem Hydrochloride

    MATSUNAE Hiroaki , DOUNO Hiroshi , YAMADA Shinichi , NISHIDA Takuo , OZAKI Yasuhiko , SHIBATANI Takeji , TOSA Tetsuya

    Journal of fermentation and bioengineering 79(1), 28-32, 1995-01-25

    参考文献18件 被引用文献7件

  • <no title>

    SERVI S.

    Synthesis 1990, 1-25

    DOI 被引用文献12件

  • <no title>

    SUGAI T.

    Tetrahedron 51, 11987, 1995

    DOI 被引用文献6件

各種コード

  • NII論文ID(NAID)
    10003739247
  • NII書誌ID(NCID)
    AA00603318
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    03667022
  • データ提供元
    CJP書誌  J-STAGE 
ページトップへ