Synthesis of L-enantiomers of 4′-thioarabinofuranosyl pyrimidine nucleosides

被引：47

作者：

Satoh, H

Yoshimura, Y

Sakata, S

Miura, S

Machida, H

Matsuda, A

机构：

[1] Yamasa Corp, Div Biochem, Choshi, Chiba 288, Japan

[2] Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 060, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1998年 / 8卷 / 09期

关键词：

D O I：

10.1016/S0960-894X(98)00161-9

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

L-Enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides were synthesized from D-xylose. Methyl 2,3,5-tri-O-benzyl-D-xylofuranoside 6 was converted to the corresponding xylitol 7, which was treated with MsCl and then Na2S to give 1,4-anhydro-L-4-thioarabitol 8. As previously reported, Pummerer rearrangement of 8 followed by glycosylation with a silylated thymine and N4-acetylcytosine derivative and deprotection gave the corresponding alpha- and beta-L-4'-thioarabinofuranosyl pyrimidine nucleosides, (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：989 / 992

页数：4

相关论文

共 18 条

[1]

BRANALT J, 1994, J ORG CHEM, V59, P1783

[2] (-)-2'-DEOXY-3'-THIACYTIDINE IS A POTENT, HIGHLY SELECTIVE INHIBITOR OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 AND TYPE-2 REPLICATION INVITRO [J].

COATES, JAV ;

CAMMACK, N ;

JENKINSON, HJ ;

JOWETT, AJ ;

JOWETT, MI ;

PEARSON, BA ;

PENN, CR ;

ROUSE, PL ;

VINER, KC ;

CAMERON, JM .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (04) :733-739

[3] THE SEPARATED ENANTIOMERS OF 2'-DEOXY-3'-THIACYTIDINE (BCH-189) BOTH INHIBIT HUMAN-IMMUNODEFICIENCY-VIRUS REPLICATION INVITRO [J].

COATES, JAV ;

CAMMACK, N ;

JENKINSON, HJ ;

MUTTON, IM ;

PEARSON, BA ;

STORER, R ;

CAMERON, JM ;

PENN, CR .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (01) :202-205

[4] 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

[5] Structure-activity relationships of 2'-deoxy-2',2'-difluoro-L-erythro-pentofuranosyl nucleosides [J].

Kotra, LP ;

Xiang, YJ ;

Newton, MG ;

Schinazi, RF ;

Cheng, YC ;

Chu, CK .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (22) :3635-3644

[6] Cell kill kinetics of an antineoplastic nucleoside, 1-(2-deoxy-2-methylene-beta-D-erythro-pentofuranosyl)cytosine [J].

Ono, T ;

Fujii, A ;

Yamagami, K ;

Hosoya, M ;

Okumoto, T ;

Sakata, S ;

Matsuda, A ;

Sasaki, T .

BIOCHEMICAL PHARMACOLOGY, 1996, 52 (08) :1279-1285

[7] PREPARATION AND ANTITUMOR ACTIVITY OF 4'-THIO ANALOGS OF 2,2'-ANHYDRO-1-BETA-D-ARABINOFURANOSYLCYTOSINE [J].

OTOTANI, N ;

WHISTLER, RL .

JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (05) :535-537

[8] 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

[9] ACTIVITIES OF THE 4 OPTICAL ISOMERS OF 2',3'-DIDEOXY-3'-THIACYTIDINE (BCH-189) AGAINST HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 IN HUMAN-LYMPHOCYTES [J].

SCHINAZI, RF ;

CHU, CK ;

PECK, A ;

MCMILLAN, A ;

MATHIS, R ;

CANNON, D ;

JEONG, LS ;

BEACH, JW ;

CHOI, WB ;

YEOLA, S ;

LIOTTA, DC .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (03) :672-676

[10] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 2'-DEOXY-4'-THIOPYRIMIDINE NUCLEOSIDES [J].

SECRIST, JA ;

TIWARI, KN ;

RIORDAN, JM ;

MONTGOMERY, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) :2361-2366