Synthesis of 9-[2',3'-dideoxy-2',3'-bis-C-hydroxymethyl-alpha-L-threofuranosyl] adenine and its 4'-thio analog as potential antiviral agents

被引：13

作者：

Kikuchi, Y

Kurata, H

Nishiyama, S

Yamamura, S

Kato, K

机构：

[1] NIPPON KAYAKU CO LTD,PHARMACEUT GRP,RES LABS,KITA KU,TOKYO 115,JAPAN

[2] KEIO UNIV,FAC SCI & TECHNOL,DEPT CHEM,YOKOHAMA,KANAGAWA 223,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(97)01035-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiomerically pure synthesis or 9-[2',3'-dideoxy-2-'3'-bis-C-hydrosymethyl-alpha-L-threorunnosyl]adenine and its 4'-thio analog was achieved via coupling or silylated 6-chloropurine with 1-O-acetyfuranose derivative 17 and its 4'-thio analog 24, respectively, prepared from (+)-diethyl L-tartrate. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：4795 / 4798

页数：4

相关论文

共 17 条

[1] SYNTHESIS AND ANTIVIRAL ACTIVITY OF 3'-DEOXY-3'-C-HYDROXYMETHYL NUCLEOSIDES [J].

BAMFORD, MJ ;

COE, PL ;

WALKER, RT .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2494-2501

[2] ANTIVIRAL ACTIVITY SPECTRUM AND TARGET OF ACTION OF DIFFERENT CLASSES OF NUCLEOSIDE ANALOGS [J].

DECLERCQ, E .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1994, 13 (6-7) :1271-1295

[3] THE SYNTHESIS AND ANTIVIRAL ACTIVITY OF SOME 4'-THIO-2'-DEOXY NUCLEOSIDE ANALOGS [J].

DYSON, MR ;

COE, PL ;

WALKER, RT .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) :2782-2786

[4] AIDS-DRIVEN NUCLEOSIDE CHEMISTRY [J].

HURYN, DM ;

OKABE, M .

CHEMICAL REVIEWS, 1992, 92 (08) :1745-1768

[5] PHOTOCATALYZED ADDITION OF ALCOHOLS TO 5-SUBSTITUTED 2,5-DIHYDROFURAN-2-ONES - NOVEL SYNTHESIS OF (3'R)-2',3'-DIDEOXY-3'-HYDROXYMETHYL NUCLEOSIDES [J].

MANN, J ;

WEYMOUTHWILSON, AC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (21) :3141-3148

[6] SYNTHESIS AND ANTIVIRAL ACTIVITY OF ADENOSINE DEAMINASE-RESISTANT OXETANOCIN A DERIVATIVES - 2-HALOGENO-OXETANOCIN-A [J].

MASUDA, A ;

KITAGAWA, M ;

TANAKA, A ;

SAITO, S ;

SHIMADA, N ;

IKEDA, R ;

HOSHINO, H ;

DAIKOKU, T ;

NISHIYAMA, Y .

JOURNAL OF ANTIBIOTICS, 1993, 46 (06) :1034-1037

[7] TOTAL SYNTHESIS OF IONOPHORE ANTIBIOTIC X-14547A [J].

NICOLAOU, KC ;

PAPAHATJIS, DP ;

CLAREMON, DA ;

MAGOLDA, RL ;

DOLLE, RE .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1440-1456

[8]

NORWECK DW, 1989, TETRAHEDRON LETT, V30, P6263

[9] Synthesis and anti-herpes virus activity of 2'-deoxy-4'-thiopyrimidine nucleosides [J].

Rahim, SG ;

Trivedi, N ;

BogunovicBatchelor, MV ;

Hardy, GW ;

Mills, G ;

Selway, JWT ;

Snowden, W ;

Littler, E ;

Coe, PL ;

Basnak, I ;

Whale, RF ;

Walker, RT .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (03) :789-795

[10]

SANGHVI YS, 1994, SYNTHESIS-STUTTGART, P1163