PUMMERER REARRANGEMENT OF SELENIUM-CONTAINING URACIL NUCLEOSIDES

被引：11

作者：

HARAGUCHI, K ^{[1
]}

SAITO, S ^{[1
]}

TANAKA, H ^{[1
]}

MIYASAKA, T ^{[1
]}

机构：

[1] SHOWA UNIV,SCH PHARMACEUT SCI,HATANODAI 1-5-8,SHINAGAWA KU,TOKYO 142,JAPAN

来源：

NUCLEOSIDES & NUCLEOTIDES | 1992年 / 11卷 / 2-4期

关键词：

D O I：

10.1080/07328319208021720

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：

Pummerer-type rearrangement of uracil nucleosides having a phenylseleno group in the 2'-, 3'-, and 5'-positions took place upon oxidation with MCPBA in CH2Cl2 followed by treatment with acid anhydrides to yield alpha-acyloxyselenides.

引用

页码：483 / 493

页数：11

共 19 条

[1] A HIGHLY STEREOSELECTIVE GLYCOSYLATION OF 2-(PHENYLSELENENYL)-2,3-DIDEOXYRIBOSE DERIVATIVE WITH THYMINE - SYNTHESIS OF 3'-DEOXY-2',3'-DIDEHYDROTHYMIDINE AND 3'-DEOXYTHYMIDINE [J].

CHU, CK ;

BABU, JR ;

BEACH, JW ;

AHN, SK ;

HUANG, HQ ;

JEONG, LS ;

LEE, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1418-1420

[2] SELENIUM NUCLEOPHILES FOR THE PREPARATION OF ANTIVIRAL NUCLEOSIDES [J].

COSFORD, NDP ;

SCHINAZI, RF .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2161-2165

[3] A PUMMERER-TYPE REARRANGEMENT OF SELENIDES [J].

GALAMBOS, G ;

SIMONIDESZ, V .

TETRAHEDRON LETTERS, 1982, 23 (42) :4371-4372

[4]

HARAGUCHI K, 1989, SYNTHESIS-STUTTGART, P434

[5] CLEAVAGE OF CYCLIC ETHERS INCLUDING OXETANE AND OXOLANE WITH A HIGHLY NUCLEOPHILIC SPECIES OF PHENYLSELENIDE ANION [J].

HARAGUCHI, K ;

TANAKA, H ;

HAYAKAWA, H ;

MIYASAKA, T .

CHEMISTRY LETTERS, 1988, (06) :931-934

[6] PREPARATION AND REACTIONS OF 2'-VINYL AND 3'-VINYL BROMIDES OF URACIL NUCLEOSIDES - VERSATILE SYNTHONS FOR ANTI-HIV AGENTS [J].

HARAGUCHI, K ;

ITOH, Y ;

TANAKA, H ;

MIYASAKA, T .

TETRAHEDRON LETTERS, 1991, 32 (28) :3391-3394

[7] NUCLEOSIDIC ENOL ESTERS - A VERSATILE TOOL FOR THE SYNTHESIS OF 3'-CARBON-SUBSTITUTED NUCLEOSIDES [J].

HARAGUCHI, K ;

TANAKA, H ;

ITOH, Y ;

MIYASAKA, T .

TETRAHEDRON LETTERS, 1991, 32 (06) :777-780

[8]

HARAGUCHI K, 1991, IN PRESS J ORG CHEM, V56

[9] 4',5'-UNSATURATED 5'-HALOGENATED NUCLEOSIDES - MECHANISM-BASED AND COMPETITIVE INHIBITORS OF S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE [J].

JARVI, ET ;

MCCARTHY, JR ;

MEHDI, S ;

MATTHEWS, DP ;

EDWARDS, ML ;

PRAKASH, NJ ;

BOWLIN, TL ;

SUNKARA, PS ;

BEY, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :647-656

[10]

LIOTTA D, 1977, TETRAHEDRON LETT, P4365

← 1 2 →