methyl 2,3-anhydro-5-O-trityl-α-D-ribofuranoside | 40147-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 2,3-anhydro-5-O-trityl-α-D-ribofuranoside
• 英文别名: (1R,2S,4R,5R)-2-methoxy-4-(trityloxymethyl)-3,6-dioxabicyclo[3.1.0]hexane
• CAS: 40147-69-1
• 化学式: C₂₅H₂₄O₄
• 分子量: 388.463
• InChiKey: IPTGADYNRWJWSJ-YCAMKHIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,3-anhydro-5-O-trityl-α-D-ribofuranoside 在 咪唑 、 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 、 magnesium 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 103.0h， 生成 methyl 3-O-(t-butyldimethylsilyl)-2-deoxy-2-C-(3-hydroxypropyl)-5-O-trityl-α-D-arabinofuranoside
  参考文献：
  名称：

  Reaction of 2-Deoxy-2-C-(3-bromoacetoxypropyl)-α-D-arabinofuranosides with Oligonucleotide¹

  摘要：

  Reaction of methyl 2-deoxy-2-C-(3-bromoacetoxypropyl)-alpha-D-arabinofuranosides, prepared from methyl 2,3-anhydro-alpha-D-ribofuranoside, with oligodeoxyribonucleotide (21mer) in acetonitrile-H2O (pH 7) and subsequent treatment with piperidine resulted in the cleavage of the nucleotide chain at the position G, A, and C.

  DOI：

  10.1080/15257779408013209
• 作为产物：
  描述：

  三苯基氯甲烷 、 2,3-anhydro-α-D-ribofuranoside de methyle 在 吡啶 作用下， 反应 24.0h， 以79%的产率得到methyl 2,3-anhydro-5-O-trityl-α-D-ribofuranoside
  参考文献：
  名称：

  Reaction of 2-Deoxy-2-C-(3-bromoacetoxypropyl)-α-D-arabinofuranosides with Oligonucleotide¹

  摘要：

  Reaction of methyl 2-deoxy-2-C-(3-bromoacetoxypropyl)-alpha-D-arabinofuranosides, prepared from methyl 2,3-anhydro-alpha-D-ribofuranoside, with oligodeoxyribonucleotide (21mer) in acetonitrile-H2O (pH 7) and subsequent treatment with piperidine resulted in the cleavage of the nucleotide chain at the position G, A, and C.

  DOI：

  10.1080/15257779408013209

文献信息

• Regioselective Introduction of 2-Propynyl Groups into the C-2 or C-3 Position of Furanoside Ring
  作者：Dai Kubota、Oyo Mitsunobu

  DOI：10.1246/cl.1997.517

  日期：1997.6

  The reaction of methyl 2,3-anhydro-α-D-ribofuranoside or methyl 2,3-anhydro-5,6-O-cyclohexylidene-α-D-allofuranoside with 2-propynyl metallic reagents exclusively gave the corresponding 2-C-(2-propynyl)-arabino-pentofuranosides and 2-C-(2-propynyl)-altro-hexofuranosides, respectively. In contrast, the β-anomers were selectively attacked at the position 3 to afford the corresponding 3-C-(2-propynyl)furanosides

  甲基 2,3-脱水-α-D-呋喃核糖苷或甲基 2,3-脱水-5,6-O-亚环己基-α-D-异呋喃糖苷与 2-丙炔基金属试剂反应完全得到相应的 2-C- (2-propynyl)-arabino-pentofuranosides 和 2-C-(2-propynyl)-altro-hexofuranosides 分别。相比之下，β-端基异构体在位置 3 处被选择性攻击以提供相应的 3-C-(2-丙炔基)呋喃糖苷。
• Reaction of 2-Deoxy-2-C-(3-bromoacetoxypropyl)-α-D-arabinofuranosides with Oligonucleotide¹
  作者：S. Mori、A. Katoh、H. Takenaka、H. Tanaka、H. Kaji、T. Samejima、O. Mitsunobu

  DOI：10.1080/15257779408013209

  日期：1994.12

  Reaction of methyl 2-deoxy-2-C-(3-bromoacetoxypropyl)-alpha-D-arabinofuranosides, prepared from methyl 2,3-anhydro-alpha-D-ribofuranoside, with oligodeoxyribonucleotide (21mer) in acetonitrile-H2O (pH 7) and subsequent treatment with piperidine resulted in the cleavage of the nucleotide chain at the position G, A, and C.