PHENYLSULFENYL D-RIBOFURANOSIDES AS EFFICIENT RIBOSYL DONORS - APPLICATION TO THE SYNTHESIS OF [1'-C-13]-(DEOXY)NUCLEOSIDES

被引：37

作者：

CHANTELOUP, L ^{[1
]}

BEAU, JM ^{[1
]}

机构：

[1] UNIV ORLEANS,CNRS,BIOCHIM STRUCT LAB,BP 6759,F-45067 ORLEANS 2,FRANCE

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 37期

关键词：

ANOMERIC SULFOXIDES; SILYLATED NUCLEOBASES; 1'-C-13]-NUCLEOSIDES; 2'-DEOXYNUCLEOSIDES;

D O I：

10.1016/S0040-4039(00)79089-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Readily available phenylsulfenyl 2,3,5-tri-O-benzoyl-beta-D-ribofuranoside glycosylates silylated nucleobases in a fast, high-yielding and stereoselective reaction promoted by trimethylsilyl trifluoromethanesulfonate. The method has been applied to the synthesis of [1'-C-13] labelled nucleosides further transformed to building blocks ready for oligodeoxynucleotide construction.

引用

页码：5347 / 5350

页数：4

共 15 条

[1] 2,3,5-TRI-O-BENZYL-D-RIBOSYL AND -L-ARABINOSYL BROMIDES [J].

BARKER, R ;

FLETCHER, HG .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (11) :4605-&

[2] SYNTHESIS OF 1,2-TRANS-RELATED 1-THIOGLYCOSIDE ESTERS [J].

FERRIER, RJ ;

FURNEAUX, RH .

CARBOHYDRATE RESEARCH, 1976, 52 (DEC) :63-68

[3] GLYCOSYLATION OF UNREACTIVE SUBSTRATES [J].

KAHNE, D ;

WALKER, S ;

CHENG, Y ;

VANENGEN, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6881-6882

[4] (C-13)-SUBSTITUTED ERYTHRONUCLEOSIDES - SYNTHESIS AND CONFORMATIONAL-ANALYSIS BY H-1 AND C-13 NMR-SPECTROSCOPY [J].

KLINE, PC ;

SERIANNI, AS .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1772-1777

[5] C-13-ENRICHED RIBONUCLEOSIDES - SYNTHESIS AND APPLICATION OF C-13-H-1 AND C-13-C-13 SPIN-COUPLING CONSTANTS TO ASSESS FURANOSE AND N-GLYCOSIDE BOND CONFORMATIONS [J].

KLINE, PC ;

SERIANNI, AS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7373-7381

[6] NUCLEOSIDE SYNTHESIS FROM THIOGLYCOSIDES [J].

KNAPP, S ;

SHIEH, WC .

TETRAHEDRON LETTERS, 1991, 32 (30) :3627-3630

[7] THE CHARACTERIZATION OF ABASIC SITES IN DNA HETERODUPLEXES BY SITE SPECIFIC LABELING WITH C-13 [J].

MANOHARAN, M ;

RANSOM, SC ;

MAZUMDER, A ;

GERLT, JA ;

WILDE, JA ;

WITHKA, JA ;

BOLTON, PH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1620-1622

[8] COEXISTENCE OF CONFORMATIONS IN A DNA HETERODUPLEX REVEALED BY SITE SPECIFIC LABELING WITH C-13-LABELED NUCLEOTIDES [J].

MANOHARAN, M ;

GERLT, JA ;

WILDE, JA ;

WITHKA, JM ;

BOLTON, PH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7217-7219

[9] APPLICATION OF 4-DIMENSIONAL HETERONUCLEAR NMR TO THE STRUCTURE DETERMINATION OF A UNIFORMLY C-13 LABELED RNA [J].

NIKONOWICZ, EP ;

PARDI, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (03) :1082-1083

[10] EINE NEUE, EINFACHE SYNTHESE DES 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSIDES [J].

RECONDO, EF ;

RINDERKNECHT, H .

HELVETICA CHIMICA ACTA, 1959, 42 (04) :1171-1173

← 1 2 →