Synthesis of L- and D-β-3′-deoxy-3′,3′-difluoronucleosides

被引:20
作者
Xu, XH
Qiu, XL
Zhang, XG
Qing, FL
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[2] Donghua Univ, Inst Biol Sci & Biotechnol, Shanghai 201620, Peoples R China
关键词
D O I
10.1021/jo052652h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Both (L)- and D-beta-3'-deoxy-3',3'-difluoronucleosides were synthesized starting from the key intermediate difluorohomoallyl alcohol 11. Deoxo-Fluor was accidentally found to be efficient in reversing the hydroxyl configuration of 34, and the desired product 41 was provided in good yield.
引用
收藏
页码:2820 / 2824
页数:5
相关论文
共 41 条
[1]   Facile cleavage of carbohydrate benzyl ethers and benzylidene acetals using the NaBrO3/Na2S2O4 reagent under two-phase conditions [J].
Adinolfi, M ;
Barone, G ;
Guariniello, L ;
Iadonisi, A .
TETRAHEDRON LETTERS, 1999, 40 (48) :8439-8441
[2]   SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].
AGROFOGLIO, L ;
SUHAS, E ;
FARESE, A ;
CONDOM, R ;
CHALLAND, SR ;
EARL, RA ;
GUEDJ, R .
TETRAHEDRON, 1994, 50 (36) :10611-10670
[3]  
[Anonymous], 1991, Fluorine in Bioorganic Chemistry
[4]  
Banks R.E., 1994, ORGANOFLUORINE CHEM
[5]  
BANKS RE, 1979, ORGANOFLURINE CHEM T
[6]   FLUORINE SUBSTITUTED ANALOGS OF NUCLEOSIDES AND NUCLEOTIDES [J].
BERGSTROM, D ;
ROMO, E ;
SHUM, P .
NUCLEOSIDES & NUCLEOTIDES, 1987, 6 (1-2) :53-63
[7]   3',3'-DIFLUORO-3'-DEOXYTHYMIDINE - COMPARISON OF ANTI-HIV ACTIVITY TO 3'-FLUORO-3'-DEOXYTHYMIDINE [J].
BERGSTROM, DE ;
MOTT, AW ;
DECLERCQ, E ;
BALZARINI, J ;
SWARTLING, DJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (18) :3369-3372
[8]  
BERGSTROM DE, 1988, FLUORINE CONTAINING, P259
[9]   Practical synthesis of a potent hepatitis C virus RNA replication inhibitor [J].
Bio, MM ;
Xu, F ;
Waters, M ;
Williams, JM ;
Savary, KA ;
Cowden, CJ ;
Yang, CH ;
Buck, E ;
Song, ZGJ ;
Tschaen, DM ;
Volante, RP ;
Reamer, RA ;
Grabowski, EJJ .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (19) :6257-6266
[10]   SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES [J].
BORTHWICK, AD ;
BIGGADIKE, K .
TETRAHEDRON, 1992, 48 (04) :571-623