BETA-SELECTIVE SYNTHESIS OF 2'-DEOXYNUCLEOSIDES BY THE COUPLING OF 2-DEOXY-1-THIO-D-THREO-PENTOFURANOSIDES WITH SILYLATED THYMINE

被引：27

作者：

SUGIMURA, H

SUJINO, K

OSUMI, K

机构：

[1] The Noguchi Institute, 173, 1-8-1, Kaga, Itabashi-ku Tokyo

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 18期

关键词：

BETA-2'-DEOXYNUCLEOSIDE; 2-DEOXY-1-THIO-D-THREO-PENTOFURANOSIDE; SILYLATED THYMINE; N-BROMOSUCCINIMIDE;

D O I：

10.1016/S0040-4039(00)92229-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The coupling of the 3,5-O-isopropylidene derivative of phenyl 2-deoxy-1-thio-D-threo-pentofuranoside with silylated thymine in the presence of N-bromosuccinimide yielded 1-(2-deoxy-beta-D-threo-pentofuranosyl)thymine with highly anomeric selectivity.

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页码：2515 / 2516

页数：2

相关论文

共 17 条

[1] STEREOSELECTIVE SYNTHESIS OF ANOMERS OF 5-SUBSTITUTED 2'-DEOXYURIDINES [J].

AOYAMA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (06) :2073-2077

[2] TARGETS AND STRATEGIES FOR THE ANTIVIRAL CHEMOTHERAPY OF AIDS [J].

DECLERCQ, E .

TRENDS IN PHARMACOLOGICAL SCIENCES, 1990, 11 (05) :198-205

[3]

DECLERCQ E, 1989, J ANTIMICROB CHEMOTH, V23, P35

[4] NEW ACQUISITIONS IN THE DEVELOPMENT OF ANTI-HIV AGENTS [J].

DECLERCQ, E .

ANTIVIRAL RESEARCH, 1989, 12 (01) :1-19

[5]

DIANA GD, 1989, ANNU REP MED CHEM, V24, P129

[6] NUCLEOSIDES .16. FURTHER STUDIES OF ANHYDRONUCLEOSIDES [J].

FOX, JJ ;

MILLER, NC .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (04) :936-&

[7] NUCLEOSIDES .5. MONOMESYLATES OF 1-(2]-DEOXY-BETA-D-LYXOFURANOSYL)THYMINE [J].

HORWITZ, JP ;

CHUA, J ;

NOEL, M .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (07) :2076-&

[8] STEREOSELECTIVITY IN THE COUPLING REACTION BETWEEN 2-PHENYLTHIO-2,3-DIDEOXYRIBOSE AND SILYLATED PYRIMIDINE-BASES [J].

KAWAKAMI, H ;

EBATA, T ;

KOSEKI, K ;

MATSUSHITA, H ;

NAOI, Y ;

ITOH, K .

CHEMISTRY LETTERS, 1990, (08) :1459-1462

[9] THE SYNTHESIS OF 2'-DEOXYADENOSINE VIA STEREOSPECIFIC COUPLING REACTION [J].

KAWAKAMI, H ;

MATSUSHITA, H ;

NAOI, Y ;

ITOH, K ;

YOSHIKOSHI, H .

CHEMISTRY LETTERS, 1989, (02) :235-238

[10] IODONIUM PROMOTED REACTIONS OF DISARMED THIOGLYCOSIDES [J].

KONRADSSON, P ;

UDODONG, UE ;

FRASERREID, B .

TETRAHEDRON LETTERS, 1990, 31 (30) :4313-4316