Methyl 5-O-benzoyl-3-C<(benzoyloxy)methyl>-2,3-dideoxy-β-D-erythro-pentofuranose | 69827-96-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 5-O-benzoyl-3-C<(benzoyloxy)methyl>-2,3-dideoxy-β-D-erythro-pentofuranose
• 英文别名: Methyl 5-O-benzoyl-3-C[(benzoyloxy)methyl]-2,3-dideoxy-β-D-erythro-pentofuranose；[(2S,3R,5R)-2-(benzoyloxymethyl)-5-methoxyoxolan-3-yl]methyl benzoate
• CAS: 69827-96-9
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: NAIPEKPVGYMXQQ-GUDVDZBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲醇 、 [(1S,2S,3S)-3-羟基-1,2-环丁烷二基]二(亚甲基)二苯甲酸酯 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 Methyl 5-O-benzoyl-3-C<(benzoyloxy)methyl>-2,3-dideoxy-β-D-erythro-pentofuranose 、 Methyl 5-O-benzoyl-3-C<(benzoyloxy)methyl>-2,3-dideoxy-α-D-erythro-pentofuranose
  参考文献：
  名称：

  A Novel Approach toward the Synthesis of Chiral 2,3-Dideoxy Nucleosides and Their Carbocyclic Analogs

  摘要：

  Photochemical ring-expansion of chiral 2(S),3(R)-bis[(benzoyloxy) methyl] cyclobutanone (3) in the presence of alcohols and acidic N-H functional groups gives anomeric mixtures of acetals and N-amino acetals, respectively, with retention of stereochemistry of the ring substituents. In the presence of purine and 6-chloropurine the corresponding protected nucleosides are-obtained. The photoadduct with 6-chloropurine is converted to the known medicinally active deprotected adenine nucleoside with methanolic ammonia. One-carbon homologation of ketone 3 with diazomethane produces the corresponding optically pure cyclopentanone 8 with retention of stereochemistry. This ketone is converted to the optically pure cyclopentylamine 10 in two steps. Racemic amine 10 has been used as a key intermediate in the preparation of carbocyclic nucleosides.

  DOI：

  10.1021/jo00087a029

文献信息

• A novel approach towards 2,3-dideoxyriboside synthesis
  作者：Edward Lee-Ruff、Jiang Ji-Long、Wan Wei-Qin

  DOI：10.1016/s0040-4039(00)60562-2

  日期：1993.1

  A short synthesis of 2,3-dideoxy-3(S)-C-hydroxymethyl ribosides is described. The key step involves a photochemical ring-expansion of a chiral cyclobutanone which occurs stereospecifically.
• US5473063A
  申请人：——

  公开号：US5473063A

  公开（公告）日：1995-12-05
• US6121431A
  申请人：——

  公开号：US6121431A

  公开（公告）日：2000-09-19
• A Novel Approach toward the Synthesis of Chiral 2,3-Dideoxy Nucleosides and Their Carbocyclic Analogs
  作者：Edward Lee-Ruff、Wei-Qin Wan、Ji-Long Jiang

  DOI：10.1021/jo00087a029

  日期：1994.4

  Photochemical ring-expansion of chiral 2(S),3(R)-bis[(benzoyloxy) methyl] cyclobutanone (3) in the presence of alcohols and acidic N-H functional groups gives anomeric mixtures of acetals and N-amino acetals, respectively, with retention of stereochemistry of the ring substituents. In the presence of purine and 6-chloropurine the corresponding protected nucleosides are-obtained. The photoadduct with 6-chloropurine is converted to the known medicinally active deprotected adenine nucleoside with methanolic ammonia. One-carbon homologation of ketone 3 with diazomethane produces the corresponding optically pure cyclopentanone 8 with retention of stereochemistry. This ketone is converted to the optically pure cyclopentylamine 10 in two steps. Racemic amine 10 has been used as a key intermediate in the preparation of carbocyclic nucleosides.