Oligonucleotide synthesis. Part 21. Synthesis of ribooligonucleotides using the 4-methoxybenzyl group as a new protecting group for the 2'-hydroxyl group

H Takaku, K Kamaike, H Tsuchiya

Index: Takaku, Hiroshi; Kamaike, Kazuo; Tsuchiya, Hiromichi Journal of Organic Chemistry, 1984 , vol. 49, # 1 p. 51 - 56

Full Text: HTML

Citation Number: 47

Abstract

The 4-methoxybenzyl group was introduced to protect the 2'-hydroxyl group of uridine, cytidine, and N?-benzoylguanosine by treatment of 2', 3 '-0-(dibutylstannylene) uridine or NaH-treated nucleosides with 4-methoxybenzyl bromide. The 2'-0-(4methoxybenzyl) nucleosides can be used as useful starting materials for the synthesis of 3', 5 '-linked ribooligonucleotides. The 4-methoxybenzyl group wm removed rapidly from the ...

Related Articles:

Mild, versatile, and chemoselective indium (III) triflate-catalyzed deprotection of acetonides under microwave heating conditions

[Golden, Kathryn C.; Gregg, Brian T.; Quinn, John F. Tetrahedron Letters, 2010 , vol. 51, # 31 p. 4010 - 4013]

Simple method for fast deprotection of nucleosides by triethylamine-catalyzed methanolysis of acetates in aqueous medium

[Meier, Lidiane; Monteiro, Gustavo C.; Baldissera, Rodrigo A.M.; Sa, Marcus Mandolesi Journal of the Brazilian Chemical Society, 2010 , vol. 21, # 5 p. 859 - 866]

A catalytic method for chemoselective detritylation of 5′-tritylated nucleosides under mild and heterogeneous conditions using silica sulfuric acid as a recyclable …

[Khalafi-Nezhad, Ali; Parhami, Abolfath; Soltani Rad, Mohammad Navid; Zolfigol, Mohammad Ali; Zare, Abdolkarim Tetrahedron Letters, 2007 , vol. 48, # 30 p. 5219 - 5222]

Highly efficient synthesis of 2′, 3′-didehydro-2′, 3′-dideoxy-β-nucleosides through a sulfur-mediated reductive 2′, 3′-trans-elimination. From …

[Robles, Rafael; Rodriguez, Concepcion; Alvarez De Cienfuegos, Luis; Mota, Antonio J. Tetrahedron Asymmetry, 2004 , vol. 15, # 5 p. 831 - 838]

Methoxyethoxymethyl group for the protection of uracil residue in oligoribonucleotide synthesis

[Takaku, Hiroshi; Ueda, Souichi; Ito, Tsunehiko Tetrahedron Letters, 1983 , vol. 24, # 48 p. 5363 - 5366]

More Articles...