ENZYMATIC-SYNTHESIS OF OPTICALLY-ACTIVE (S)-(+)-2-HYDROXYMETHYL-3,4-DIHYDRO-2H-PYRAN AND (S)-(+)-2-ACETOXYMETHYL-3,4-DIHYDRO-2H-PYRAN

被引:13
|
作者
KANG, SK
JEON, JH
YAMAGUCHI, T
HONG, RK
KO, BS
机构
[1] Department of Chemistry, Sung Kyun Kwan University, Suwon, 440-746, Natural Science Campus
关键词
D O I
10.1016/0957-4166(94)00361-E
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Porcine pancreas lipase(PPL)-catalyzed acetylation of(+/-)-2-hydroxymethyl-3,4-dihydro-2H-pyran with vinyl acetate in organic solvent afforded (S)-(+)-2-acetoxymethyl-3,4-dihydro-2H-pyran. Alternatively, (+/-)-2-acetoxymethyl-3,4-dihydro-2H-pyran was resolved via hydrolysis catalyzed by PPL in acetone-phosphate buffer system to afford (S)-(+)-2-hydroxymethyl-3,4-dihydro-2H-pyran with high enantiomeric purity.
引用
收藏
页码:97 / 100
页数:4
相关论文
共 50 条
  • [31] CERIC AMMONIUM-NITRATE CATALYZED PROTECTION OF ALCOHOLS BY 3,4-DIHYDRO-2H-PYRAN
    MAITY, G
    ROY, SC
    SYNTHETIC COMMUNICATIONS, 1993, 23 (12) : 1667 - 1671
  • [32] On the Nucleophilic Reactions of 5-Trifluoroacetyl-3,4-dihydro-2H-pyranZur nucleophilen Reaktion von 5-Trifluoracetyl-3,4-dihydro-2H-pyran
    Shizheng Zhu
    Guolin Xu
    Chaoyue Qin
    Qianli Chu
    Yong Xu
    Monatshefte für Chemie / Chemical Monthly, 1999, 130 : 671 - 680
  • [33] ELABORATION OF 3,4-DIHYDRO-2H-PYRAN VIA ETA-2-(3-OXACYCLOHEXYNE) ZIRCONOCENE
    HARRIS, MCJ
    WHITBY, RJ
    BLAGG, J
    SYNLETT, 1993, (09) : 705 - 707
  • [34] Measurements for the dissociation conditions of methane hydrate in the presence of 2,5-dihydrofuran and 3,4-dihydro-2H-pyran
    Cheng, Chih-Tien
    Chen, Li-Jen
    Lin, Shiang-Tai
    Tang, Muoi
    Chen, Po-Chun
    Chen, Yan-Ping
    FLUID PHASE EQUILIBRIA, 2013, 338 : 114 - 118
  • [35] A STUDY OF SENSITIZED PHOTOOXYGENATION OF 3, 4-DIHYDRO-2H-PYRAN
    CAO, Y
    CHEN, JX
    ZHANG, BW
    MING, YF
    ACTA CHIMICA SINICA, 1985, 43 (08) : 761 - 766
  • [36] Directly linked C-disaccharides: Structures of two 3,4-dihydro-2H-pyran derivatives
    Ianelli, S
    Nardelli, M
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 : 2853 - 2857
  • [37] THE THERMAL UNIMOLECULAR DECOMPOSITION OF 3,4-DIHYDRO-2H-PYRAN BEHIND REFLECTED SHOCK-WAVES
    SAITO, K
    ADACHI, K
    WATANABE, M
    SHIMOFUJI, K
    IMAMURA, A
    CHEMICAL PHYSICS LETTERS, 1990, 165 (05) : 383 - 385
  • [38] Control of reactivity of novolac resins:: the use of 3,4-dihydro-2H-pyran as a labile protecting group
    Bateman, SA
    Caulfield, MJ
    Munton, JR
    Solomon, DH
    POLYMER, 2001, 42 (15) : 6339 - 6345
  • [39] NEW SYNTHETIC ROUTES TO SPIROACETALS - THE 3,4-DIHYDRO-2H-PYRAN APPROACH TO (+/-)-TALAROMYCIN-B
    KOCIENSKI, P
    YEATES, C
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (09): : 1879 - 1883
  • [40] ADDITION-REARRANGEMENT REACTIONS OF N-(ARYLSULFONYLOXY)AMINES AND 3,4-DIHYDRO-2H-PYRAN
    HOFFMAN, RV
    SALVADOR, JM
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08): : 1375 - 1380