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
  • [21] Total synthesis of (±)-O-methyl PD 116740
    Hauser, FM
    Dorsch, WA
    Mal, D
    ORGANIC LETTERS, 2002, 4 (13) : 2237 - 2239
  • [22] SYNTHESIS AND HYBRIDIZATION STUDIES ON 2 COMPLEMENTARY NONA(2'-O-METHYL)RIBONUCLEOTIDES
    INOUE, H
    HAYASE, Y
    IMURA, A
    IWAI, S
    MIURA, K
    OHTSUKA, E
    NUCLEIC ACIDS RESEARCH, 1987, 15 (15) : 6131 - 6148
  • [23] Synthesis of oligoribonucleotides containing pyrimidine 2′-O-[(hydroxyalkoxy)methyl]ribonucleosides
    Bobkov, Georgii V.
    Brilliantov, Kirill V.
    Mikhailov, Sergey N.
    Rozenski, Jef
    Van Aerschot, Arthur
    Herdewijn, Piet
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2006, 71 (06) : 804 - 819
  • [24] APPROACHES TO THE SYNTHESIS OF CANDELABRONE SYNTHESIS OF (+/-)-MARGOCILIN O-METHYL ETHER
    BURNELL, RH
    GIRARD, M
    SYNTHETIC COMMUNICATIONS, 1990, 20 (16) : 2469 - 2472
  • [25] Synthesis of O-methyl epi-heliannuol E
    Sabui, SK
    Venkateswaran, RV
    TETRAHEDRON, 2003, 59 (42) : 8375 - 8381
  • [26] TOTAL SYNTHESIS OF (+/-)-DIMETHYL SECOLOGANOSIDE O-METHYL ETHER
    CHANG, NC
    DAY, HM
    LU, WF
    JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17): : 4083 - 4088
  • [27] SYNTHESIS AND PROPERTIES OF AN INITIATION CODON ANALOG CONSISTING OF 2'-O-METHYL NUCLEOTIDES
    HIRAO, I
    OKUBO, M
    ISHIKAWA, M
    MIURA, K
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1990, 9 (08): : 1113 - 1122
  • [28] TOTAL SYNTHESIS OF (+/-)-GIGANTINE AND ITS O-METHYL ETHER
    CHOUDHURY, AM
    CHEMISTRY & INDUSTRY, 1971, (21) : 578 - +
  • [29] PHOTOSENSITIVE PROTECTION OF CARBOXYL GROUP AND SYNTHESIS OF 3 O-METHYL DERIVATIVES OF GIBBERELLIN A3
    SEREBRYAKOV, EP
    SUSLOVA, LM
    KUCHEROV, VF
    TETRAHEDRON, 1978, 34 (03) : 345 - 351
  • [30] 2′,3′-O-phosphonoalkylidene derivatives of ribonucleosides:: Synthesis and reactivity
    Endová, M
    Masojídková, M
    Budesinsky, M
    Rosenberg, I
    TETRAHEDRON, 1998, 54 (37) : 11151 - 11186