ENZYMATIC RESOLUTION OF ALPHA-ACETOXYSULFIDES - A NEW APPROACH TO THE SYNTHESIS OF HOMOCHIRAL S,O-ACETALS

被引:23
作者
MILTON, J
BRAND, S
JONES, MF
RAYNER, CM
机构
[1] UNIV LEEDS,SCH CHEM,LEEDS LS2 9JT,W YORKSHIRE,ENGLAND
[2] GLAXO RES & DEV LTD,CHEM DEV,STEVENAGE SG1 2NY,HERTS,ENGLAND
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/0957-4166(95)00248-N
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A novel enzymatic resolution of alpha-acetoxysulfides using Pseudomonas fluorescens lipase is reported. Selectivity is highly dependent on the substrate and solvent, with enantiomeric excesses of >95% in some cases. We believe these are the first examples of enzymatic resolutions of an S,O-acetal.
引用
收藏
页码:1903 / 1906
页数:4
相关论文
共 42 条
[1]  
ARCHER NJ, 1994, SYNLETT, P617
[2]   SYNTHESIS OF ENANTIOMERICALLY PURE (2'R,5'S)-(-)-1-[2-(HYDROXYMETHYL)OXATHIOLAN-5-YL]CYTOSINE AS A POTENT ANTIVIRAL AGENT AGAINST HEPATITIS-B VIRUS (HBV) AND HUMAN-IMMUNODEFICIENCY-VIRUS (HIV) [J].
BEACH, JW ;
JEONG, LS ;
ALVES, AJ ;
POHL, D ;
KIM, HO ;
CHANG, CN ;
DOONG, SL ;
SCHINAZI, RF ;
CHENG, YC ;
CHU, CK .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2217-2219
[3]   A NOVEL CLASS OF 1,3-OXATHIOLANE NUCLEOSIDE ANALOGS HAVING POTENT ANTI-HIV ACTIVITY [J].
BELLEAU, B ;
BRASILI, L ;
CHAN, L ;
DIMARCO, MP ;
ZACHARIE, B ;
NGUYENBA, N ;
JENKINSON, HJ ;
COATES, JAV ;
CAMERON, JM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (08) :1723-1728
[4]   INSITU COMPLEXATION DIRECTS THE STEREOCHEMISTRY OF N-GLYCOSYLATION IN THE SYNTHESIS OF OXATHIOLANYL AND DIOXOLANYL NUCLEOSIDE ANALOGS [J].
CHOI, WB ;
WILSON, LJ ;
YEOLA, S ;
LIOTTA, DC ;
SCHINAZI, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9377-9379
[5]  
CHU C K, 1991, Journal of Organic Chemistry, V56, P6503, DOI 10.1021/jo00023a010
[6]   THE SEPARATED ENANTIOMERS OF 2'-DEOXY-3'-THIACYTIDINE (BCH-189) BOTH INHIBIT HUMAN-IMMUNODEFICIENCY-VIRUS REPLICATION INVITRO [J].
COATES, JAV ;
CAMMACK, N ;
JENKINSON, HJ ;
MUTTON, IM ;
PEARSON, BA ;
STORER, R ;
CAMERON, JM ;
PENN, CR .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (01) :202-205
[7]   ORGANOALKALI COMPOUNDS BY RADICAL-ANION INDUCED REDUCTIVE METALATION OF PHENYL THIOETHERS [J].
COHEN, T ;
BHUPATHY, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (04) :152-161
[8]   A STRUCTURAL BASIS FOR THE CHIRAL PREFERENCES OF LIPASES [J].
CYGLER, M ;
GROCHULSKI, P ;
KAZLAUSKAS, RJ ;
SCHRAG, JD ;
BOUTHILLIER, F ;
RUBIN, B ;
SERREQI, AN ;
GUPTA, AK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3180-3186
[9]  
DAVIES HG, 1990, CHEM LETT, P33
[10]  
DELUCCHI O, 1990, ORG REACTIONS, V40, P157