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]   STRUCTURAL VARIATIONS IN 3,4-DIHYDRO-2H-PYRAN KETALS - ACYL AND ARYL WARFARIN DERIVATIVES [J].
RUGGIERO, G ;
THAGGARD, AL ;
VALENTE, EJ ;
EGGLESTON, DS .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1990, 46 :629-637
[32]   On the Nucleophilic Reactions of 5-Trifluoroacetyl-3,4-dihydro-2H-pyranZur nucleophilen Reaktion von 5-Trifluoracetyl-3,4-dihydro-2H-pyran [J].
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 [J].
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 [J].
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 [J].
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 [J].
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 [J].
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 [J].
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 [J].
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 [J].
HOFFMAN, RV ;
SALVADOR, JM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08) :1375-1380