A practical synthesis of L-FMAU from L-arabinose

被引:45
作者
Du, JF [1 ]
Choi, Y [1 ]
Lee, K [1 ]
Chun, BK [1 ]
Hong, JH [1 ]
Chu, CK [1 ]
机构
[1] Univ Georgia, Coll Pharm, Dept Pharmaceut & Biomed Sci, Ctr Drug Discovery, Athens, GA 30602 USA
来源
NUCLEOSIDES & NUCLEOTIDES | 1999年 / 18卷 / 02期
关键词
D O I
10.1080/15257779908043066
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
A practical synthesis of 2'-deoxy-2'-fluoro-5-methyl-beta-L-arabinofuranosyl uracil (14, L-FMAU) was developed from L-arabinose. L-Arabinose was converted to L-ribose 5, which was used for the synthesis of bromosugar 12 via 2,3,5-O-tribenzoyl-1-O-acetyl-beta-L-ribofuranose 8, which was subjected to condensation with silylated thymine and the resulting protected L-FMAU 13 was deprotected to afford L-FMAU in 14 steps in 8 % overall yield.
引用
收藏
页码:187 / 195
页数:9
相关论文
共 23 条
[1]  
ABE Y, 1980, CHEM PHARM BULL, V28, P1324
[2]   A NEW SYNTHESIS OF D-ERYTHROSE DERIVATIVES FROM D-ARABINOSE [J].
BALLOU, CE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (01) :165-166
[3]   BMS-200475, a novel carbocyclic 2'-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro [J].
Bisacchi, GS ;
Chao, ST ;
Bachard, C ;
Daris, JP ;
Innaimo, S ;
Jacobs, GA ;
Kocy, O ;
Lapointe, P ;
Martel, A ;
Merchant, Z ;
Slusarchyk, WA ;
Sundeen, JE ;
Young, MG ;
Colonno, R ;
Zahler, R .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (02) :127-132
[4]   A STEREOCONTROLLED SYNTHESIS OF 1,3,5-TRI-O-BENZOYL-ALPHA-D-RIBOFURANOSE [J].
BRODFUEHRER, PR ;
SAPINO, C ;
HOWELL, HG .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (14) :2597-2598
[5]   Triethylamine poly(hydrogen fluorides) in the synthesis of a fluorinated nucleoside glycon [J].
Chou, TS ;
Becke, LM ;
OToole, JC ;
Carr, MA ;
Parker, BE .
TETRAHEDRON LETTERS, 1996, 37 (01) :17-20
[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]   A PRELIMINARY TRIAL OF LAMIVUDINE FOR CHRONIC HEPATITIS-B INFECTION [J].
DIENSTAG, JL ;
PERRILLO, RP ;
SCHIFF, ER ;
BARTHOLOMEW, M ;
VICARY, C ;
RUBIN, M .
NEW ENGLAND JOURNAL OF MEDICINE, 1995, 333 (25) :1657-1661
[8]   LONG-TERM REMISSION OF CHRONIC HEPATITIS-B AFTER ALPHA-INTERFERON THERAPY [J].
KORENMAN, J ;
BAKER, B ;
WAGGONER, J ;
EVERHART, JE ;
DIBISCEGLIE, AM ;
HOOFNAGLE, JH .
ANNALS OF INTERNAL MEDICINE, 1991, 114 (08) :629-634
[9]  
Koszalka G. W., 1996, Antiviral Research, V30, pA43
[10]   Structure-activity relationships of 1-(2-deoxy-2-fluoro-beta-L-arabinofuranosyl)pyrimidine nucleosides as anti-hepatitis B virus agents [J].
Ma, TW ;
Pai, SB ;
Zhu, YL ;
Lin, JS ;
Shanmuganathan, K ;
Du, JF ;
Wang, CG ;
Kim, H ;
Newton, MG ;
Cheng, YC ;
Chu, CK .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (14) :2835-2843