ethyl 4-O-acetyl-1,5-anhydro-2,3-dideoxy-DL-5-thio-hex-2-enopyranouronate | 1112147-59-7

• 英文名称: ethyl 4-O-acetyl-1,5-anhydro-2,3-dideoxy-DL-5-thio-hex-2-enopyranouronate
• 英文别名: ethyl 3-acetyloxy-3,6-dihydro-2H-thiopyran-2-carboxylate
• CAS: 1112147-59-7
• 化学式: C₁₀H₁₄O₄S
• 分子量: 230.285
• InChiKey: GQVFTCQABDJSBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-O-acetyl-1,5-anhydro-2,3-dideoxy-DL-5-thio-hex-2-enopyranouronate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到1,5-anhydro-2,3-dideoxy-5-thio-DL-threo-hex-2-enitol
  参考文献：
  名称：

  Synthesis of methyl 4,6-O-benzylidene-2,3-dideoxy-5-thio-β-dl-threo-hex-2-enopyranoside via hetero-Diels–Alder reaction and unusual stabilities of 1,5-anhydro-4,6-O-benzylidene 2,3-dideoxy-5-thio-dl-threo-hex-2-enitol

  摘要：

  The title compound was prepared via hetero-Diels-Alder reaction of 1-acetoxy-1,3-butadiene and thioaldehyde, followed by Pummerer rearrangement. Different from the corresponding sugar and 5a-carba sugar, C-inside isomer of 1,5-anhydro-4,6-O-benzylidene-2,3-dideoxy-5-thio-DL-thero-hex-2-enitol was found to be thermodynamically more stable than the corresponding O-inside one and these thermodynamic stabilities were corroborated by ab initio calculations. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.025
• 作为产物：
  描述：

  1-乙酰氧基-1,3-丁二烯 、 ethyl thioxoacetate 在 三乙胺 、 碳酸氢钠 作用下， 以 甲醇 、 甲苯 、 水 为溶剂， 反应 0.5h， 以10.5 g的产率得到ethyl 4-O-acetyl-1,5-anhydro-2,3-dideoxy-DL-5-thio-hex-2-enopyranouronate
  参考文献：
  名称：

  Synthesis of methyl 4,6-O-benzylidene-2,3-dideoxy-5-thio-β-dl-threo-hex-2-enopyranoside via hetero-Diels–Alder reaction and unusual stabilities of 1,5-anhydro-4,6-O-benzylidene 2,3-dideoxy-5-thio-dl-threo-hex-2-enitol

  摘要：

  The title compound was prepared via hetero-Diels-Alder reaction of 1-acetoxy-1,3-butadiene and thioaldehyde, followed by Pummerer rearrangement. Different from the corresponding sugar and 5a-carba sugar, C-inside isomer of 1,5-anhydro-4,6-O-benzylidene-2,3-dideoxy-5-thio-DL-thero-hex-2-enitol was found to be thermodynamically more stable than the corresponding O-inside one and these thermodynamic stabilities were corroborated by ab initio calculations. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.025