methyl (4S)-4,5-epothiopentanoate | 270569-23-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (4S)-4,5-epothiopentanoate
• 英文别名: methyl 3-[(2R)-thiiran-2-yl]propanoate
• CAS: 270569-23-8
• 化学式: C₆H₁₀O₂S
• 分子量: 146.21
• InChiKey: HRXCSGHQCJOYOQ-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (4S)-4,5-epothiopentanoate 在 盐酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 (4R)-hydroxymethyl-4-thiobutyro-1,4-lactone
  参考文献：
  名称：

  Two approaches to the enantioselective synthesis of (4R)-(−)-4-hydroxymethyl-4-thiobutyro-1,4-lactone

  摘要：

  Enantiomerically pure (4R)-4-hydroxymethyl-4-thiobutyro-1,4-lactone [(5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone (12)] and derivatives were synthesized by two enantiospecific sequences employing D-ribono-1,4-lactone (1) and L-glutamic acid (6) as chiral templates. The key step in the first approach was the SmI2-promoted 2,3-deoxygenation of a 4-thio-L-lyxono-1,4-lactone derivative, prepared from 1. The other strategy, which starts from 6, involves the (5S)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone (8) as chiral precursor. This was converted into a 4,5-thiirane derivative via the corresponding 4,5-epoxide. Regioselective opening of the thiirane ring by acetate followed by O-deacetylation gave 12 (40% overall yield from 8). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00568-6
• 作为产物：
  描述：

  methyl (S)-3-(oxiran-2-yl)propanoate 在 硫脲 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以83%的产率得到methyl (4S)-4,5-epothiopentanoate
  参考文献：
  名称：

  Two approaches to the enantioselective synthesis of (4R)-(−)-4-hydroxymethyl-4-thiobutyro-1,4-lactone

  摘要：

  Enantiomerically pure (4R)-4-hydroxymethyl-4-thiobutyro-1,4-lactone [(5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone (12)] and derivatives were synthesized by two enantiospecific sequences employing D-ribono-1,4-lactone (1) and L-glutamic acid (6) as chiral templates. The key step in the first approach was the SmI2-promoted 2,3-deoxygenation of a 4-thio-L-lyxono-1,4-lactone derivative, prepared from 1. The other strategy, which starts from 6, involves the (5S)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone (8) as chiral precursor. This was converted into a 4,5-thiirane derivative via the corresponding 4,5-epoxide. Regioselective opening of the thiirane ring by acetate followed by O-deacetylation gave 12 (40% overall yield from 8). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00568-6

文献信息

• Two approaches to the enantioselective synthesis of (4R)-(−)-4-hydroxymethyl-4-thiobutyro-1,4-lactone
  作者：Patricia A Zunszain、Oscar Varela

  DOI：10.1016/s0957-4166(99)00568-6

  日期：2000.2

  Enantiomerically pure (4R)-4-hydroxymethyl-4-thiobutyro-1,4-lactone [(5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone (12)] and derivatives were synthesized by two enantiospecific sequences employing D-ribono-1,4-lactone (1) and L-glutamic acid (6) as chiral templates. The key step in the first approach was the SmI2-promoted 2,3-deoxygenation of a 4-thio-L-lyxono-1,4-lactone derivative, prepared from 1. The other strategy, which starts from 6, involves the (5S)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone (8) as chiral precursor. This was converted into a 4,5-thiirane derivative via the corresponding 4,5-epoxide. Regioselective opening of the thiirane ring by acetate followed by O-deacetylation gave 12 (40% overall yield from 8). (C) 2000 Elsevier Science Ltd. All rights reserved.