Methyl 3-deoxy-3-(1,3-dithian-2-yl)-α-D-arabino-pentofuranoside | 142890-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 3-deoxy-3-(1,3-dithian-2-yl)-α-D-arabino-pentofuranoside
• 英文别名: (2S,3S,4S,5S)-4-(1,3-dithian-2-yl)-5-(hydroxymethyl)-2-methoxyoxolan-3-ol
• CAS: 142890-39-9
• 化学式: C₁₀H₁₈O₄S₂
• 分子量: 266.383
• InChiKey: RCGHQURHWIZKAE-HXFLIBJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 3-deoxy-3-(1,3-dithian-2-yl)-α-D-arabino-pentofuranoside 在 三氟化硼乙醚 、 sodium hydride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 9.0h， 生成 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：

  1,3-二噻烷 、 methyl 2,3-anhydro-α-D-lyxofuranoside 在 正丁基锂 作用下， 生成 Methyl 2-deoxy-2-(1,3-dithian-2-yl)-α-D-xylo-pentofuranoside 、 Methyl 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