[(2S,3R,4R,5R)-5-(6-Amino-purin-9-yl)-2-hydroxymethyl-4-methoxy-tetrahydro-furan-3-yl]-acetic acid methyl ester | 221537-21-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: [(2S,3R,4R,5R)-5-(6-Amino-purin-9-yl)-2-hydroxymethyl-4-methoxy-tetrahydro-furan-3-yl]-acetic acid methyl ester
• 英文别名: methyl 2-[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-yl]acetate
• CAS: 221537-21-9
• 化学式: C₁₄H₁₉N₅O₅
• 分子量: 337.335
• InChiKey: WQTJUWDLEFVVPN-FQFVAWICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4R,5R)-5-(6-Amino-purin-9-yl)-2-hydroxymethyl-4-methoxy-tetrahydro-furan-3-yl]-acetic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 ((2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-{6-[1-methyl-pyrrolidin-(2Z)-ylideneamino]-purin-9-yl}-tetrahydro-furan-3-yl)-acetic acid pentafluorophenyl ester
  参考文献：
  名称：

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

  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.

  DOI：

  10.1016/s0040-4039(99)00147-1
• 作为产物：
  描述：

  2'-methyl-adenosine 在 palladium on activated charcoal 吡啶 、 chromium(VI) oxide 、 四丁基氟化铵 、 氢气 、 乙酸酐 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 118.0h， 生成 [(2S,3R,4R,5R)-5-(6-Amino-purin-9-yl)-2-hydroxymethyl-4-methoxy-tetrahydro-furan-3-yl]-acetic acid methyl ester
  参考文献：
  名称：

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

  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.

  DOI：

  10.1016/s0040-4039(99)00147-1

文献信息

• An expeditious synthesis of 3′-α-carboxymethyl-2′-O-methyl ribonucleosides
  作者：Peter von Matt、Thomas Lochmann、Rudolf Kesselring、Karl-Heinz Altmann

  DOI：10.1016/s0040-4039(99)00147-1

  日期：1999.3

  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.