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
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
收藏
页码:1873 / 1876
页数:4
相关论文
共 50 条
  • [41] Mapping 2′-O-methyl groups in ribosomal RNA
    Maden, BEH
    METHODS, 2001, 25 (03) : 374 - 382
  • [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] 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
  • [45] 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
  • [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 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
  • [48] SYNTHESIS OF 2],5]-O-PROTECTED RIBONUCLEOSIDES
    SMRT, J
    HOLY, A
    TETRAHEDRON LETTERS, 1967, (11) : 981 - &
  • [49] Aminoglycoside conjugated 2'-O-methyl oligoribonucleotides:: Solid phase synthesis and artificial nuclease activity
    Virta, Pasi
    CHEMISTRY OF NUCLEIC ACID COMPONENTS, 2008, 10 : 150 - 154
  • [50] Synthesis of 4′-C-aminoalkyl-2′-O-methyl modified RNA and their biological properties
    Koizumi, Kana
    Maeda, Yusuke
    Kano, Toshifumi
    Yoshida, Hisae
    Sakamoto, Taiichi
    Yamagishi, Kenji
    Ueno, Yoshihito
    BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (12) : 3521 - 3534