Efficient synthesis of 2-deoxy-L-erythro-pentose (2-deoxy-L-ribose) from L-arabinose

被引:23
作者
Chong, YH [1 ]
Chu, CK [1 ]
机构
[1] Univ Georgia, Coll Pharm, Ctr Drug Discovery, Dept Pharmaceut & Biomed Sci, Athens, GA 30602 USA
关键词
2-deoxy-L-erythro-pentose; 2-deoxy-L-ribose; L-nucleosides; L-arabinose; free-radical deoxygenation;
D O I
10.1016/S0008-6215(01)00329-9
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
An efficient and practical route for the large-scale synthesis of 2-deoxy-L-erythro-pentose (2-deoxy-L-ribose) starting from L-arabinose was developed using Barton-type free-radical deoxygenation reaction as a key step. The radical precursor. a phenoxythiocarbonyl ester, was prepared in situ. and the most efficient deoxygenation was achieved by slow addition of tributyltin hydride to the reaction mixture. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:397 / 402
页数:6
相关论文
共 30 条
[1]  
AGROFOGLIO LA, 1998, CHEM L NUCLEOSIDES, P285
[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]   Anti-human immunodeficiency and anti-hepatitis B virus activities of beta-L-2',3'-dideoxy purine nucleosides [J].
Bolon, PJ ;
Wang, PY ;
Chu, CK ;
Gosselin, G ;
Boudou, V ;
Pierra, C ;
Mathe, C ;
Imbach, JL ;
Faraj, A ;
Alaoui, MA ;
Sommadossi, JP ;
Pai, SB ;
Zhu, YL ;
Lin, JS ;
Cheng, YC ;
Schinazi, RF .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (14) :1657-1662
[4]  
CHANG CN, 1992, J BIOL CHEM, V267, P22414
[5]  
CHANG CN, 1992, J BIOL CHEM, V267, P13938
[6]   USE OF 2'-FLUORO-5-METHYL-BETA-L-ARABINOFURANOSYLURACIL AS A NOVEL ANTIVIRAL AGENT FOR HEPATITIS-B VIRUS AND EPSTEIN-BARR-VIRUS [J].
CHU, CK ;
MA, TW ;
SHANHMUGANATHAN, K ;
WANG, CG ;
XIANG, YJ ;
PAI, SB ;
YAO, GQ ;
SOMMADOSSI, JP ;
CHENG, YC .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1995, 39 (04) :979-981
[7]   DEOXY-SUGARS .5. A REINVESTIGATION OF THE GLYCAL METHOD FOR THE SYNTHESIS OF 2-DEOXY-D-RIBOSE AND 2-DEOXY-L-RIBOSE [J].
DERIAZ, RE ;
OVEREND, WG ;
STACEY, M ;
TEECE, EG ;
WIGGINS, LF .
JOURNAL OF THE CHEMICAL SOCIETY, 1949, (JUL) :1879-1883
[8]   A practical synthesis of L-FMAU from L-arabinose [J].
Du, JF ;
Choi, Y ;
Lee, K ;
Chun, BK ;
Hong, JH ;
Chu, CK .
NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (02) :187-195
[9]   THE ANTI-HEPATITIS-B VIRUS ACTIVITIES, CYTOTOXICITIES, AND ANABOLIC PROFILES OF THE (-) AND (+) ENANTIOMERS OF CIS-5-FLUORO-1-[2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]CYTOSINE [J].
FURMAN, PA ;
DAVIS, M ;
LIOTTA, DC ;
PAFF, M ;
FRICK, LW ;
NELSON, DJ ;
DORNSIFE, RE ;
WURSTER, JA ;
WILSON, LJ ;
FYFE, JA ;
TUTTLE, JV ;
MILLER, WH ;
CONDREAY, L ;
AVERETT, DR ;
SCHINAZI, RF ;
PAINTER, GR .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (12) :2686-2692
[10]  
GOSSELIN G, 1994, CR ACAD SCI III-VIE, V317, P85