An industrial process for synthesizing lodenosine (FddA)

被引:10
作者
Izawa, K
Takamatsu, S
Katayama , S
Hirose, N
Kozai, S
Maruyama, T
机构
[1] Ajinomoto Co Inc, AminoSci Labs, Kawasaki Ku, Kawasaki, Kanagawa 2108681, Japan
[2] Tokushima Bunri Univ, Fac Pharmaceut Sci, Yamashiro, Tokushima, Japan
关键词
anti-HIV; nucleosides; lodenosine; fluorination; radical reduction;
D O I
10.1081/NCN-120021951
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
Two industrial synthetic approaches to Lodenosine (1, FddA, 9-(2,3-dideoxy-2-fluoro-p-D-threo-pentofuranosyl) adenine) via a purine riboside or a purine 3'-deoxyriboside are described. Several novel applications of deoxygenation and fluorination methods are compared considering reaction yields, economy, safety and environmental concerns.
引用
收藏
页码:507 / 517
页数:11
相关论文
共 28 条
[1]  
BENNUASKALMOWSKI B, 1994, B SOC CHIM BELG, V103, P453
[2]   A FACILE CONVERSION OF PRIMARY OR SECONDARY ALCOHOLS WITH N-PERFLUOROBUTANESULFONYL FLUORIDE/1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE INTO THEIR CORRESPONDING FLUORIDES [J].
BENNUASKALMOWSKI, B ;
VORBRUGGEN, H .
TETRAHEDRON LETTERS, 1995, 36 (15) :2611-2614
[3]  
BILLICH A, 1999, CURRENT OPINION ANTI, V1, P179
[4]   PROGRESS OF THE BARTON-MCCOMBIE METHODOLOGY - FROM TIN HYDRIDES TO SILANES [J].
CHATGILIALOGLU, C ;
FERRERI, C .
RESEARCH ON CHEMICAL INTERMEDIATES, 1993, 19 (08) :755-775
[5]   2'-fluoro-2',3'-dideoxyarabinosyladenine (F-ddA): Activity against drug-resistant human immunodeficiency virus strains and clades A-E [J].
Driscoll, JS ;
Mayers, DL ;
Bader, JP ;
Weislow, OS ;
Johns, DG ;
Buckheit, RW .
ANTIVIRAL CHEMISTRY & CHEMOTHERAPY, 1997, 8 (02) :107-111
[6]  
Graul A., 1998, Drugs of the Future, V23, P1176, DOI 10.1358/dof.1998.023.11.474025
[7]   NUCLEIC-ACID RELATED-COMPOUNDS .49. REGIOSPECIFIC AND STEREOSELECTIVE CONVERSION OF RIBONUCLEOSIDES TO 3'-DEOXYNUCLEOSIDES - A HIGH-YIELD 3-STAGE SYNTHESIS OF CORDYCEPIN FROM ADENOSINE [J].
HANSSKE, F ;
ROBINS, MJ .
TETRAHEDRON LETTERS, 1985, 26 (36) :4295-4298
[8]   SYNTHESIS AND ANTI-HIV ACTIVITY OF VARIOUS 2'-SUBSTITUTED AND 3'-SUBSTITUTED 2',3'-DIDEOXYADENOSINES - A STRUCTURE ACTIVITY ANALYSIS [J].
HERDEWIJN, P ;
PAUWELS, R ;
BABA, M ;
BALZARINI, J ;
DECLERCQ, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (11) :2131-2137
[9]   (2R,3S,5S)-2-acetoxy-3-fluoro-5-(p-toluoyloxymethyl)tetrahydrofuran:: a key intermediate for the practical synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (FddA) [J].
Jin, FQ ;
Wang, DJ ;
Confalone, PN ;
Pierce, ME ;
Wang, Z ;
Xu, GY ;
Choudhury, A ;
Nguyen, D .
TETRAHEDRON LETTERS, 2001, 42 (29) :4787-4789
[10]   2',3'-DIDEOXY-2'-FLUORO-ARA-A - AN ACID-STABLE PURINE NUCLEOSIDE ACTIVE AGAINST HUMAN-IMMUNODEFICIENCY-VIRUS (HIV) [J].
MARQUEZ, VE ;
TSENG, CKH ;
KELLEY, JA ;
MITSUYA, H ;
BRODER, S ;
ROTH, JS ;
DRISCOLL, JS .
BIOCHEMICAL PHARMACOLOGY, 1987, 36 (17) :2719-2722