MDPSCL2:: A new protecting group for chemoselective synthesis of 2′-0-alkylated guanosines

被引：10

作者：

Chow, S

Wen, K

Sanghvi, YS

Theodorakis, EA

机构：

[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

[2] ISIS Pharmaceut Inc, Carlsbad Res Ctr, Carlsbad, CA USA

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2003年 / 22卷 / 5-8期

关键词：

D O I：

10.1081/NCN-120021959

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An improved strategy for the synthesis of 2'-O-methyl-guanosine (6) and 2'-MOE-guanosine (8) is reported. The regioselectivity of the alkylation was attained using a novel silicon-based protecting group, methylene-bis (diiso-propyl-silylchloride) (MDPSCl2, 2). The alkylation proceeded in a chemoselective manner using NaHMDS as the base and MeCl or MOE-Br as the appropriate electrophiles.

引用

收藏

页码：583 / 587

页数：5

相关论文

共 23 条

[1] THE EVALUATION OF 2'-SUBSTITUTED AND 6'-SUBSTITUTED CARBOCYCLIC NUCLEOSIDES AS BUILDING-BLOCKS FOR ANTISENSE OLIGONUCLEOTIDES [J].

ALTMANN, KH ;

BEVIERRE, MO ;

DEMESMAEKER, A ;

MOSER, HE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (05) :431-436

[2] Improved synthetic approaches toward 2′-O-methyl-adenosine and guanosine and their N-acyl derivatives [J].

Beigelman, L ;

Haeberli, P ;

Sweedler, D ;

Karpeisky, A .

TETRAHEDRON, 2000, 56 (08) :1047-1056

[3]

BEIGELMAN L, 1999, Patent No. 5962575

[4] SIMPLIFIED AND COST-EFFECTIVE SYNTHESES OF FULLY PROTECTED PHOSPHORAMIDITE MONOMERS SUITABLE FOR THE ASSEMBLY OF OLIGO(2'-O-ALLYLRIBONUCLEOTIDES) [J].

BEIJER, B ;

GROTLI, M ;

DOUGLAS, ME ;

SPROAT, BS .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1994, 13 (09) :1905-1927

[5] EFFICIENT SYNTHESIS OF 2'-O-ALKYL RIBONUCLEOSIDES USING TRICHLOROACETIMIDATE D-RIBOFURANOSIDES AS RIBOSYL DONORS [J].

CHANTELOUP, L ;

THUONG, NT .

TETRAHEDRON LETTERS, 1994, 35 (06) :877-880

[6]

COOK PD, 1999, Patent No. 5861493

[7] Potential roles of antisense technology in cancer chemotherapy [J].

Crooke, ST .

ONCOGENE, 2000, 19 (56) :6651-6659

[8]

CROOKE ST, 2001, ANTISENSE DRUG TECHN

[9] Functional genomics and target validation approaches using antisense oligonucleotide technology [J].

Dean, NM .

CURRENT OPINION IN BIOTECHNOLOGY, 2001, 12 (06) :622-625

[10] Antisense oligonucleotides: An evolving technology for the modulation of gene expression in human disease [J].

Green, DW ;

Roh, H ;

Pippin, J ;

Drebin, JA .

JOURNAL OF THE AMERICAN COLLEGE OF SURGEONS, 2000, 191 (01) :93-105