4-C-allyl-1-S-acetyl-2,4-dideoxy-3-O-mesyl-6-O-methoxymethyl-1-sulfanyl-α,β-D-arabino-hexopyranoside | 677301-75-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-C-allyl-1-S-acetyl-2,4-dideoxy-3-O-mesyl-6-O-methoxymethyl-1-sulfanyl-α,β-D-arabino-hexopyranoside
• CAS: 677301-75-6
• 化学式: C₁₄H₂₄O₇S₂
• 分子量: 368.472
• InChiKey: ZNUFZGVFZQVYGM-OANWKOAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  23.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-C-allyl-1-S-acetyl-2,4-dideoxy-3-O-mesyl-6-O-methoxymethyl-1-sulfanyl-α,β-D-arabino-hexopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以50%的产率得到(2S,3S)-1-methoxymethyloxy-3-vinyl-5-hexen-2-ol
  参考文献：
  名称：

  Synthesis of a Ring Fragment of 9 ,11 -Thiathromboxane A₂. Procedure for Bond C¹-C²Cleavage in Monosaccharides by an Example of D-Glucose 2-Deoxy-3-mesyl Derivative

  摘要：

  4-C-Allyl-1-S-acetyl-2,4-dideoxy-3-O-mesyl-6-O-methoxymethyl-1-sulfanyl-alpha, beta-D-arabinohexo-pyranoside treated with (Me3Si)(2)NNa in benzene at room temperature affords a bicyclic product resulting from intramolecular cyclization, and at treatment with a system MeONa-MeOH at heating suffers fragmentation furnishing (2S,3S)-1-methoxymethyloxy-3-vinyl-5-hexen-2-ol.

  DOI：

  10.1023/b:rujo.0000003161.60198.ec
• 作为产物：
  描述：

  4-C-allyl-1,6-anhydro-2,4-dideoxy-3-O-medyl-β-D-arabino-hexopyranose 在 三氟化硼乙醚 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-C-allyl-1-S-acetyl-2,4-dideoxy-3-O-mesyl-6-O-methoxymethyl-1-sulfanyl-α,β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Synthesis of a Ring Fragment of 9 ,11 -Thiathromboxane A₂. Procedure for Bond C¹-C²Cleavage in Monosaccharides by an Example of D-Glucose 2-Deoxy-3-mesyl Derivative

  摘要：

  4-C-Allyl-1-S-acetyl-2,4-dideoxy-3-O-mesyl-6-O-methoxymethyl-1-sulfanyl-alpha, beta-D-arabinohexo-pyranoside treated with (Me3Si)(2)NNa in benzene at room temperature affords a bicyclic product resulting from intramolecular cyclization, and at treatment with a system MeONa-MeOH at heating suffers fragmentation furnishing (2S,3S)-1-methoxymethyloxy-3-vinyl-5-hexen-2-ol.

  DOI：

  10.1023/b:rujo.0000003161.60198.ec