methyl 2-[(3R,4S)-4-hydroxythian-3-yl]acetate | 139237-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: methyl 2-[(3R,4S)-4-hydroxythian-3-yl]acetate
• CAS: 139237-71-1
• 化学式: C₈H₁₄O₃S
• 分子量: 190.263
• InChiKey: STSQWWLKMXHPCI-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4-Oxo-tetrahydro-thiopyran-3-yl)-acetic acid ethyl ester 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 水 为溶剂， 反应 56.0h， 生成 methyl 2-[(3R,4S)-4-hydroxythian-3-yl]acetate
  参考文献：
  名称：

  面包酵母对映体对4-氧代-3-四氢硫代吡喃基乙酸酯的对映选择性还原及其在光学纯形式前列腺素中间体的合成中的应用

  摘要：

  Bakers' yeast reduction of 4-oxo-3-tetrahydrothiopyranylacetates proceeds with high enantioselectivity, leading to optically pure diastereomeric alcohols. The synthetic utility of the present reaction is demonstrated in an expedient synthesis of (-)-(1S,2S,3S,4R)-3,4-epoxy-2-hydroxyethylcyclopentan-1-ol, a useful prostaglandin intermediate, in optically pure form using the Ramberg-Baecklund reaction as a key step.

  DOI：

  10.1016/0040-4039(91)85038-7

文献信息

• Enantioselective reduction of 4-oxo-3-tetrahydrothiopyranyl-acetates with bakers' yeast and application to the synthesis of a prostaglandin intermediate in optically pure form
  作者：Tamotsu Fujisawa、Bingidimi I. Mobele、Makoto Shimizu

  DOI：10.1016/0040-4039(91)85038-7

  日期：1991.11

  Bakers' yeast reduction of 4-oxo-3-tetrahydrothiopyranylacetates proceeds with high enantioselectivity, leading to optically pure diastereomeric alcohols. The synthetic utility of the present reaction is demonstrated in an expedient synthesis of (-)-(1S,2S,3S,4R)-3,4-epoxy-2-hydroxyethylcyclopentan-1-ol, a useful prostaglandin intermediate, in optically pure form using the Ramberg-Baecklund reaction as a key step.