EFFICIENT SYNTHESIS OF 2'-O-ALKYL RIBONUCLEOSIDES USING TRICHLOROACETIMIDATE D-RIBOFURANOSIDES AS RIBOSYL DONORS

被引：23

作者：

CHANTELOUP, L ^{[1
]}

THUONG, NT ^{[1
]}

机构：

[1] CTR BIOPHYS MOLEC,CNRS,F-45071 ORLEANS 2,FRANCE

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 06期

关键词：

O-RIBOSYL-TRICHLOROACETIMIDATES; SILYLATED NUCLEOBASES; 2'-O-ALKYL RIBONUCLEOSIDES;

D O I：

10.1016/S0040-4039(00)75987-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trichloroacetimidate-2-O-alkyl-3, 5-O-TIPS-beta-D-ribofuranoside glycosylates silylated nucleobases in a fast high-yielding and stereoselective reaction promoted by trimethylsilyl trifluoromethanesulfonate. This method has been applied to the synthesis of 2'-O-alkyl ribonucleosides further transformed to building blocks ready for oligo(2'-O-alkyl)ribonucleotide construction.

引用

页码：877 / 880

页数：4

共 20 条

[1] SYNTHESIS OF 2',3'-DIFFERENTIATED RIBONUCLEOSIDES VIA GLYCOSYLATION REACTIONS WITH 2-O-ME OR 2-O-TBDMS RIBOFURANOSE DERIVATIVES .1. PYRIMIDINE SERIES
CHAVIS, C
DUMONT, F
WIGHTMAN, RH
ZIEGLER, JC
IMBACH, JL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (02) : 202 - 206
[2] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES
COREY, EJ
VENKATESWARLU, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) : 6190 - +
[3] 2'-O-METHYL, 2'-O-ETHYL OLIGORIBONUCLEOTIDES AND PHOSPHOROTHIOATE OLIGODEOXYRIBONUCLEOTIDES AS INHIBITORS OF THE INVITRO U7 SNRNP-DEPENDENT MESSENGER-RNA PROCESSING EVENT
COTTEN, M
OBERHAUSER, B
BRUNAR, H
HOLZNER, A
ISSAKIDES, G
NOE, CR
SCHAFFNER, G
WAGNER, E
BIRNSTIEL, ML
[J]. NUCLEIC ACIDS RESEARCH, 1991, 19 (10) : 2629 - 2635
[4] THE ALLYLOXYCARBONYL GROUP FOR ALCOHOL PROTECTION - QUANTITATIVE REMOVAL OR TRANSFORMATION INTO ALLYL PROTECTING GROUP VIA PI-ALLYL COMPLEXES OF PALLADIUM
GUIBE, F
SAINTMLEUX, Y
[J]. TETRAHEDRON LETTERS, 1981, 22 (37) : 3591 - 3594
[5] THE METHYLATION OF RIBONUCLEOSIDES BY TRIMETHYL PHOSPHATE OR DIMETHYL SULFATE IN THE PRESENCE OF BORIC-ACID
HISANAGA, Y
TANABE, T
YAMAUCHI, K
KINOSHITA, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (05) : 1569 - 1570
[6] SYNTHESIS AND HYBRIDIZATION STUDIES ON 2 COMPLEMENTARY NONA(2'-O-METHYL)RIBONUCLEOTIDES
INOUE, H
HAYASE, Y
IMURA, A
IWAI, S
MIURA, K
OHTSUKA, E
[J]. NUCLEIC ACIDS RESEARCH, 1987, 15 (15) : 6131 - 6148
[7] INOUE H, 1985, NUCLEIC ACIDS RES S, V16, P165
[8] LAMOND LA, 1993, FEBS LETT, V325, P123
[9] MARKIEWICZ WT, 1979, J CHEM RES-S, P24
[10] MARKIEWICZ WT, 1979, J CHEM RES MINIPRINT, P181

← 1 2 →