An expeditious synthesis of 3′-α-carboxymethyl-2′-O-methyl ribonucleosides

被引：13

作者：

von Matt, P

Lochmann, T

Kesselring, R

Altmann, KH

机构：

[1] Novartis Pharmaceut, Summit, NJ 07901 USA

[2] Novartis Pharma AG, CH-4002 Basel, Switzerland

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(99)00147-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3'-alpha-Carboxymethyl-2'-O-methyl ribonucleosides, which are important building blocks for the construction of high affinity amide modified antisense oligonucleotides, have been synthesized from the corresponding 2'-O-methyl ribonucleosides via catalytic hydrogenation of their 3'-deoxy 3'-methoxycarbonyl-methylidene derivatives. Reduction of the olefinic double bond proceeds in good to excellent yields and with alpha/beta-product ratios > 9/1. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1873 / 1876

页数：4

共 50 条

[41] Synthesis of a complete series of O-methyl analogues of naringenin and apigenin
Bull. Korean Chem. Soc., 2007, 12 (2527-2530): : 2527 - 2530
[42] 2'(3')-O-L-(O-METHYL-3-PHENYLLACTYL)ADENOSINE - POTENTIAL ANALOG OF 2'(3')-O-AMINOACYL RIBONUCLEOSIDES
ZEMLICKA, J
OWENS, J
BIOCHIMICA ET BIOPHYSICA ACTA, 1976, 442 (01) : 71 - 75
[43] Synthesis, optical and electrochemical properties of substituted 2-cinnamoyl-1, 3-indandione O-methyl ethers
Malina, Ilze
Kampars, Valdis
Turovska, Baiba
JOURNAL OF MOLECULAR STRUCTURE, 2016, 1115 : 241 - 249
[44] Nucleotides LXIV[1]:: Synthesis, hybridization and enzymatic degradation studies of 2′-O-methyl-oligoribonucleotides and 2′-O-methyl/deoxy gapmers
Cramer, H
Pfleiderer, W
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2000, 19 (10-12) : 1765 - 1777
[45] Synthesis of 2′-C-methyl-4′-thio ribonucleosides
Dukhan, D
Bosc, E
Peyronnet, J
Storer, R
Gosselin, G
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2005, 24 (5-7) : 577 - 580
[46] CHEMICAL SYNTHESIS OF 2'-O-BENZYL AND 3'-O-BENZYL ETHERS OF RIBONUCLEOSIDES
CHRISTEN.LF
BROOM, AD
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1971, (NSEP): : 25 - &
[47] SYNTHESIS OF 2],5]-O-PROTECTED RIBONUCLEOSIDES
SMRT, J
HOLY, A
TETRAHEDRON LETTERS, 1967, (11) : 981 - &
[48] An Efficient Synthesis of O-Methyl Protected Emodin Aldehyde and Emodin Nitrile
Tarek A. Salama
Bernd Lackner
Heinz Falk
Monatshefte für Chemie / Chemical Monthly, 2003, 134 : 1113 - 1119
[49] Synthesis and biological activity of phosphonoacetate- and thiophosphonoacetate-modified 2′-O-methyl oligoribonucleotides
Threlfall, Richard N.
Torres, Adrian G.
Krivenko, Angelika
Gait, Michael J.
Caruthers, Marvin H.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (04) : 746 - 754
[50] EFFICIENT STEREOSELECTIVE SYNTHESIS OF (+/-)-SWEROSIDE AND (+/-)-SECOLOGANIN AGLUCONE O-METHYL ETHERS
HUTCHINSON, CR
MATTES, KC
NAKANE, M
PARTRIDGE, JJ
USKOKOVIC, MR
HELVETICA CHIMICA ACTA, 1978, 61 (04) : 1221 - 1225

← 1 2 3 4 5 →