Microwave-assisted selective 5′-O-trityl protection of inosine derivatives

被引：6

作者：

Casanova, Elena

Perez-Perez, Maria-Jesus

Kappe, C. Oliver

机构：

[1] Karl Franzens Univ Graz, CDLMC, A-8010 Graz, Austria

[2] Karl Franzens Univ Graz, Inst Chem, A-8010 Graz, Austria

[3] CSIC, Inst Quim Med, E-28006 Madrid, Spain

来源：

SYNLETT | 2007年 / 11期

关键词：

protecting groups; microwave synthesis; nucleosides; tritylether; medicinal chemistry;

D O I：

10.1055/s-2007-982532

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

The efficient microwave-assisted synthesis of 5'-O-trityl inosine derivatives is described. The reported protocol allows the protection of inosine derivatives in significantly higher yields and shorter reaction times than the standard thermal conditions. This procedure is particularly Suitable for modified inosines where the 5'-OH is sterically hindered (i.e. 8-bromoinosine).

引用

收藏

页码：1733 / 1735

页数：3

相关论文

共 15 条

[1]

5′-O-tritylinosine and analogues as allosteric inhibitors of human thymidine phosphorylase [J].

Casanova, Elena ;

Hernandez, Ana-Isabel ;

Priego, Eva-Maria ;

Liekens, Sandra ;

Camarasa, Maria-Jose ;

Balzarini, Jan ;

Perez-Perez, Maria-Jesus .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (18) :5562-5570

[2]

An efficient synthesis of cyclic IDP- and cyclic 8-bromo-IDP-carbocyclic-riboses using a modified hata condensation method to form an intramolecular pyrophosphate linkage as a key step. An entry to a general method for the chemical synthesis of cyclic ADP-ribose analogues [J].

Fukuoka, M ;

Shuto, S ;

Minakawa, N ;

Ueno, Y ;

Matsuda, A .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) :5238-5248

[3]

SYNTHESIS OF RNA CONTAINING INOSINE - ANALYSIS OF THE SEQUENCE REQUIREMENTS FOR THE 5' SPLICE SITE OF THE TETRAHYMENA GROUP-I INTRON [J].

GREEN, R ;

SZOSTAK, JW ;

BENNER, SA ;

RICH, A ;

USMAN, N .

NUCLEIC ACIDS RESEARCH, 1991, 19 (15) :4161-4166

[4]

NUCLEOTIDES .V. PURINE RIBONUCLEOSIDE 2',3'-CYCLIC CARBONATES . PREPARATION AND USE FOR SYNTHESIS OF 5'-MONOSUBSTITUTED NUCLEOSIDES [J].

HAMPTON, A ;

NICHOL, AW .

BIOCHEMISTRY, 1966, 5 (06) :2076-&

[5]

PURINE NUCLEOSIDES .7. DIRECT BROMINATION OF ADENOSINE DEOXYADENOSINE GUANOSINE + RELATED PURINE NUCLEOSIDES [J].

HOLMES, RE ;

ROBINS, RK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (06) :1242-&

[6]

Antiviral amphipathic oligo- and polyribonucleotides: Analogue development and biological studies [J].

Hyde, RM ;

Broom, AD ;

Buckheit, RW .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (10) :1878-1885

[7]

Controlled microwave heating in modern organic synthesis [J].

Kappe, CO .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6250-6284

[8]

Tetrabutylammonium bromide:: an efficient media for dimethoxytritylation of the 5′-hydroxyl function of nucleosides [J].

Khalafi-Nezhad, A ;

Mokhtari, B .

TETRAHEDRON LETTERS, 2004, 45 (36) :6737-6739

[9]

The nucleoside derivative 5′-O-trityl-inosine (KIN59) suppresses thymidine phosphorylase-triggered angiogenesis via a noncompetitive mechanism of action [J].

Liekens, S ;

Hernández, AI ;

Ribatti, D ;

De Clercq, E ;

Camarasa, MJ ;

Pérez-Pérez, MJ ;

Balzarini, J .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (28) :29598-29605

[10]

An improved synthesis of inosine 3′-phosphoramidite [J].

Matulic-Adamic, J ;

Beigelman, L .

SYNTHETIC COMMUNICATIONS, 2000, 30 (21) :3963-3969