Convenient synthesis of C-aza-2,3-dideoxynucleosides

被引:33
作者
Momotake, A
Togo, H
Yokoyama, M
机构
[1] Chiba Univ, Fac Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan
[2] Chiba Univ, Grad Sch Sci & Technol, Inage Ku, Chiba 2638522, Japan
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 09期
关键词
D O I
10.1039/a900689c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-Aryl-1,2,3,4-tetradeoxy-1,4-imino-D-pentitols 5 and 9f are easily synthesized from N-Boc-L-pyroglutamate I ria a successive procedure involving regioselective ring-opening, recyclization with dehydration, stereoselective reduction, and reduction of the ester group. Their structures are determined mainly by X-ray crystallography and NMR measurements. Their bioassay is also described.
引用
收藏
页码:1193 / 1200
页数:8
相关论文
共 29 条
[1]   SYNTHESIS OF AN AZATHYMIDINE AND ITS INCORPORATION INTO OLIGONUCLEOTIDES [J].
ALTMANN, KH ;
FREIER, SM ;
PIELES, U ;
WINKLER, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (15-16) :1654-1657
[2]  
BALZARINI J, 1988, MOL PHARMACOL, V33, P243
[3]   ANTI-HIV-1 ACTIVITY OF 2',3'-DIDEOXYNUCLEOSIDE ANALOGS - STRUCTURE-ACTIVITY RELATIONSHIP [J].
DECLERCQ, E ;
VANAERSCHOT, A ;
HERDEWIJN, P ;
BABA, M ;
PAUWELS, R ;
BALZARINI, J .
NUCLEOSIDES & NUCLEOTIDES, 1989, 8 (5-6) :659-671
[4]   Unusually strong binding of a designed transition-state analog to a base-excision DNA repair protein [J].
Deng, L ;
Scharer, OD ;
Verdine, GL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) :7865-7866
[5]   DIASTEREOSELECTIVE SYNTHESIS OF CHIRAL SECONDARY-AMINES WITH 2 CHIRAL CENTERS DIRECTLY ATTACHED TO THE NITROGEN ATOM [J].
ELEVELD, MB ;
HOGEVEEN, H ;
SCHUDDE, EP .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3635-3642
[6]   REGIOSELECTIVE NUCLEOPHILIC-ATTACK ON N-BOC-PYROGLUTAMATE ETHYL-ESTER [J].
EZQUERRA, J ;
DEMENDOZA, J ;
PEDREGAL, C ;
RAMIREZ, C .
TETRAHEDRON LETTERS, 1992, 33 (38) :5589-5590
[7]   A MILD 2-STEP METHOD FOR THE HYDROLYSIS METHANOLYSIS OF SECONDARY AMIDES AND LACTAMS [J].
FLYNN, DL ;
ZELLE, RE ;
GRIECO, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (14) :2424-2426
[8]   Synthesis of transition state inhibitors for N-riboside hydrolases and transferases [J].
Furneaux, RH ;
Limberg, G ;
Tyler, PC ;
Schramm, VL .
TETRAHEDRON, 1997, 53 (08) :2915-2930
[9]   LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].
GEMAL, AL ;
LUCHE, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459
[10]   A NEW CLASS OF C-NUCLEOSIDE ANALOGS - 1-(S)-ARYL-1,4-DIDEOXY-1,4-IMINO-D-RIBITOLS, TRANSITION-STATE ANALOG INHIBITORS OF NUCLEOSIDE HYDROLASE [J].
HORENSTEIN, BA ;
ZABINSKI, RF ;
SCHRAMM, VL .
TETRAHEDRON LETTERS, 1993, 34 (45) :7213-7216