A New Protocol for Selective Cleavage of Acyl Protecting Groups in 2′-O-Modified 3′,5′-O-(Tetraisopropyldisiloxane-1,3-diyl)ribonucleosides

被引：7

作者：

Drenichev, M. S. ^{[1
]}

Kulikova, I. V. ^{[1
]}

Bobkov, G. V. ^{[1
]}

Tararov, V. I. ^{[1
]}

Mikhailov, S. N. ^{[1
]}

机构：

[1] Russian Acad Sci, VA Engelhardt Mol Biol Inst, Moscow 119991, Russia

来源：

SYNTHESIS-STUTTGART | 2010年 / 22期

基金：

俄罗斯基础研究基金会;

关键词：

nucleosides; blocking group stability; tetraisopropyl-disiloxane-1; 3-diyl; protecting group; N-deacylation; O-deacylation; ACID RELATED-COMPOUNDS; DISACCHARIDE NUCLEOSIDES; OLIGONUCLEOTIDE SYNTHESIS; TETRAISOPROPYLDISILOXANE-1,3-DIYL GROUP; NUCLEASE RESISTANCE; EFFICIENT SYNTHESIS; RNA; OLIGORIBONUCLEOTIDES; POLY(ADP-RIBOSE); RIBONUCLEOSIDES;

D O I：

10.1055/s-0030-1258270

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stability of tetraisopropyldisiloxane-1,3-diyl (TIPDS) protection in nucleosides in ammonia/amine solutions in methanol and ethanol was studied. In ammonia-methanol at ambient temperature significant partial cleavage of TIPDS was observed. When ethanol was used instead of methanol this undesired side reaction was completely inhibited. It was found that commercially available 8 M methylamine-ethanol solution is the reagent of choice for selective deacylation of N- or/and O-acyl protected nucleosides without notable cleavage of 3',5'-TIPDS group. Several examples of the developed protocol for the preparation 2'-O-modified nucleosides with overall high yields are presented.

引用

页码：3827 / 3834

页数：8

共 37 条

[1] Phosphoramidite building blocks for efficient incorporation of 2′-O-aminoethoxy(and propoxy)methyl nucleosides into oligonucleotides [J].

Bobkov, Georgii V. ;

Mikhailov, Sergey N. ;

Van Aerschot, Arthur ;

Herdewijn, Piet .

TETRAHEDRON, 2008, 64 (27) :6238-6251

[2] Synthesis of oligoribonucleotides containing pyrimidine 2′-O-[(hydroxyalkoxy)methyl]ribonucleosides [J].

Bobkov, Georgii V. ;

Brilliantov, Kirill V. ;

Mikhailov, Sergey N. ;

Rozenski, Jef ;

Van Aerschot, Arthur ;

Herdewijn, Piet .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2006, 71 (06) :804-819

[3] MDPSCL2:: A new protecting group for chemoselective synthesis of 2′-0-alkylated guanosines [J].

Chow, S ;

Wen, K ;

Sanghvi, YS ;

Theodorakis, EA .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2003, 22 (5-8) :583-587

[4] Assessment of 4-nitrogenated benzyloxymethyl groups for 2′-hydroxyl protection in solid-phase RNA synthesis [J].

Cieslak, Jacek ;

Kauffman, Jon S. ;

Kolodziejski, Michelle J. ;

Lloyd, John R. ;

Beaucage, Serge L. .

ORGANIC LETTERS, 2007, 9 (04) :671-674

[5]

Cuenoud B, 1998, ANGEW CHEM INT EDIT, V37, P1288, DOI 10.1002/(SICI)1521-3773(19980518)37:9<1288::AID-ANIE1288>3.0.CO

[6]

2-U

[7]

Curtin Nicola J., 2005, Expert Reviews in Molecular Medicine, V7, P1, DOI 10.1017/S146239940500904X

[8] Disaccharide nucleosides as an important group of natural compounds [J].

Efimtseva, E. V. ;

Kulikova, I. V. ;

Mikhailov, S. N. .

MOLECULAR BIOLOGY, 2009, 43 (02) :301-312

[9] Disaccharide nucleosides and their incorporation into oligonucleotides [J].

Efimtseva, Ekaterina V. ;

Kulikova, Irina V. ;

Mikhailov, Sergey N. .

CURRENT ORGANIC CHEMISTRY, 2007, 11 (04) :337-354

[10]

Efimtseva EV, 2004, USP KHIM+, V73, P435

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