STEREOCONTROLLED SYNTHESES OF C-LINKED DEOXYRIBOSIDES OF 2-HYDROXYPYRIDINE AND 2-HYDROXYQUINOLINE

被引：26

作者：

SOLOMON, MS ^{[1
]}

HOPKINS, PB ^{[1
]}

机构：

[1] UNIV WASHINGTON,DEPT CHEM,SEATTLE,WA 98195

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 28期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)92690-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2'-Deoxy-C-ribosides 4 and 5 were prepared in optically active form by a route expected to be generally useful for the synthesis of the alpha- or beta-anomers of 2'-deoxy-C-ribosides. Key steps are the addition of an organometallic reagent to aldehyde 7, mesylation of the resulting alcohol, and stereospecific deprotection/cyclization to yield the 2'-deoxy-C-riboside (7 + 8 --> 9/10; 9 --> 11).

引用

收藏

页码：3297 / 3300

页数：4

相关论文

共 18 条

[1] SYNTHESIS AND BIOLOGICAL EVALUATION OF 3-CHLORO-4-(D-RIBOFURANOSYL)-PYRIDINE AND 3-(D-RIBOFURANOSYL)-2-PYRIDONE [J].

BELMANS, M ;

VRIJENS, I ;

ESMANS, EL ;

LEPOIVRE, JA ;

ALDERWEIRELDT, FC ;

WOTRING, LL ;

TOWNSEND, LB .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1987, 6 (1-2) :245-248

[2] DIRECT SUBSTITUTION OF 2-BENZENESULFONYL CYCLIC ETHERS USING ORGANOZINC REAGENTS [J].

BROWN, DS ;

LEY, SV .

TETRAHEDRON LETTERS, 1988, 29 (38) :4869-4872

[3]

Buchanan J.G., 1983, PROG CHEM ORG NATURA, V44, P243

[4] REGIOSELECTIVE ORTHO LITHIATION OF HALOPYRIDINES [J].

GRIBBLE, GW ;

SAULNIER, MG .

TETRAHEDRON LETTERS, 1980, 21 (43) :4137-4140

[5]

Hacksell U, 1985, Prog Med Chem, V22, P1, DOI 10.1016/S0079-6468(08)70228-5

[6]

JAMES SR, 1979, J CARB-NUCLEOS-NUCL, V6, P417

[7] DNA DYNAMICS FROM A SPIN PROBE - DEPENDENCE OF PROBE MOTION ON TETHER LENGTH [J].

KIRCHNER, JJ ;

HUSTEDT, EJ ;

ROBINSON, BH ;

HOPKINS, PB .

TETRAHEDRON LETTERS, 1990, 31 (05) :593-596

[8] NEW REACTION OF QUINOLINE - REGIOSELECTIVE METALATION OF FLUOROQUINOLINES [J].

MARSAIS, F ;

BOULEY, E ;

QUEGUINER, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 171 (03) :273-282

[9] A NEW APPROACH TO THE SYNTHESIS OF A PROTECTED 2-AMINOPURINE DERIVATIVE AND ITS INCORPORATION INTO OLIGODEOXYNUCLEOTIDES CONTAINING THE ECO-RI AND BAM-HI RECOGNITION SITES [J].

MCLAUGHLIN, LW ;

LEONG, T ;

BENSELER, F ;

PIEL, N .

NUCLEIC ACIDS RESEARCH, 1988, 16 (12) :5631-5644

[10] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28