New method for the preparation of 3'- and 2'-phosphoramidites of 2'- and 3'-difluoromethyleneuridine

被引：33

作者：

Serafinowski, PJ

Barnes, CL

机构：

[1] CRC Centre for Cancer Therapeutics, Institute of Cancer Research, Sutton, Surrey SM2 5NG

来源：

TETRAHEDRON | 1996年 / 52卷 / 23期

关键词：

D O I：

10.1016/0040-4020(96)00364-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The one step reaction of 2'- and 3'-keto derivatives of uridine 2a, 2b, 7a and 7b with bromodifluoromethyl[tris(dimethylamino)]phosphonium bromide (13) and zinc gives the corresponding 2'- and 3'-difluoromethylene nucleosides 3a, 3b, 8a and 8b in good yield. Removal of the silyl groups affords difluoromethylenated uridines 4a, 4b, 9a and 9b. Phosphitylation of 4a and 9a provides the target 2'- and 3'-phosphoramidites 5 and 10 for use in oligonucleotide synthesis. Copyright (C) 1996 Elsevier Science Ltd

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收藏

页码：7929 / 7938

页数：10

相关论文

共 22 条

[1] ADVANCES IN THE SYNTHESIS OF OLIGONUCLEOTIDES BY THE PHOSPHORAMIDITE APPROACH [J].

BEAUCAGE, SL ;

IYER, RP .

TETRAHEDRON, 1992, 48 (12) :2223-2311

[2]

BEIGELMAN L, 1995, NUCLEIC ACIDS RES, V23, P4434

[3]

CARUTHERS MH, 1987, METHOD ENZYMOL, V154, P287

[4] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[5] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[6] AN IMPROVED SYNTHESIS OF 3'-KETO-5'-O-TRITYLTHYMIDINE [J].

FROEHLICH, ML ;

SWARTLING, DJ ;

LIND, RE ;

MOTT, AW ;

BERGSTROM, DE .

NUCLEOSIDES & NUCLEOTIDES, 1989, 8 (08) :1529-1535

[7] NEW CATALYSTS AND PROCEDURES FOR THE DIMETHOXYTRITYLATION AND SELECTIVE SILYLATION OF RIBONUCLEOSIDES [J].

HAKIMELAHI, GH ;

PROBA, ZA ;

OGILVIE, KK .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (09) :1106-1113

[8] A CONVENIENT STRATEGY FOR REPLACEMENT OF THE ANOMERIC HYDROXYL GROUP BY DIFLUOROMETHYL FUNCTIONALITY IN CARBOHYDRATE-DERIVATIVES [J].

HOULTON, JS ;

MOTHERWELL, WB ;

ROSS, BC ;

TOZER, MJ ;

WILLIAMS, DJ ;

SLAWIN, AMZ .

TETRAHEDRON, 1993, 49 (36) :8087-8106

[9] TRANSFORMATION OF CARBONYL-COMPOUNDS INTO GEM-DIFLUORO COMPOUNDS WITH DIBROMODIFLUOROMETHANE ZINC REAGENT [J].

HU, CM ;

QING, FL ;

SHEN, CX .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (03) :335-338

[10] Nucleoside phosphonates. Development of synthetic methods and reagents [J].

Kers, A ;

Kers, I ;

Kraszewski, A ;

Sobkowski, M ;

Szabo, T ;

Thelin, M ;

Zain, R ;

Stawinski, J .

NUCLEOSIDES & NUCLEOTIDES, 1996, 15 (1-3) :361-378