Methyl 2,5-di-O-benzoyl-3-deoxy-3-(1,3-dithian-2-yl)-α-D-arabino-pentofuranoside | 142890-55-9

• 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 2,5-di-O-benzoyl-3-deoxy-3-(1,3-dithian-2-yl)-α-D-arabino-pentofuranoside
• CAS: 142890-55-9
• 化学式: C₂₄H₂₆O₆S₂
• 分子量: 474.599
• InChiKey: JPWACRWIOGZOLO-UGTOYMOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methyl 2,5-di-O-benzoyl-3-deoxy-3-(1,3-dithian-2-yl)-α-D-arabino-pentofuranoside 在 三氟化硼乙醚 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以80.8%的产率得到Methyl 2,5-di-O-benzoyl-3-deoxy-3-C-formyl-α-D-arabino-pentofuranoside
  参考文献：
  名称：

  Synthesis of derivatives of methyl 3-deoxy-3-C-formyl-α-d-arabino-pentofuranoside

  摘要：

  Methyl 2,3-anhydro-alpha-D-lyxofuranoside and some 5-substituted derivatives react with 2-lithio-1,3-dithiane and phenylthiomethyl-lithium at both positions of the epoxide ring. but mainly at C-3. The ratio of the adducts is affected by the nature of the 5-substituent. Appropriate desulphuration reactions of the dithioacetal and sulphide functions in the adducts gave derivatives of methyl 3-deoxy-3-C-formyl-alpha-D-arabino-pentofuranoside.

  DOI：

  10.1016/s0008-6215(00)90576-7
• 作为产物：
  描述：

  methyl 2,3-anhydro-α-D-lyxofuranoside 在 正丁基锂 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 9.5h， 生成 Methyl 2,5-di-O-benzoyl-3-deoxy-3-(1,3-dithian-2-yl)-α-D-arabino-pentofuranoside
  参考文献：
  名称：

  Synthesis of derivatives of methyl 3-deoxy-3-C-formyl-α-d-arabino-pentofuranoside

  摘要：

  Methyl 2,3-anhydro-alpha-D-lyxofuranoside and some 5-substituted derivatives react with 2-lithio-1,3-dithiane and phenylthiomethyl-lithium at both positions of the epoxide ring. but mainly at C-3. The ratio of the adducts is affected by the nature of the 5-substituent. Appropriate desulphuration reactions of the dithioacetal and sulphide functions in the adducts gave derivatives of methyl 3-deoxy-3-C-formyl-alpha-D-arabino-pentofuranoside.

  DOI：

  10.1016/s0008-6215(00)90576-7