(3S)-3-[(R)-hydroxy-[(6R,10S)-6-[(S)-hydroxy-[(3R)-4-oxothian-3-yl]methyl]-1,4-dioxa-8-thiaspiro[4.5]decan-10-yl]methyl]thian-4-one | 898826-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S)-3-[(R)-hydroxy-[(6R,10S)-6-[(S)-hydroxy-[(3R)-4-oxothian-3-yl]methyl]-1,4-dioxa-8-thiaspiro[4.5]decan-10-yl]methyl]thian-4-one
• CAS: 898826-00-1
• 化学式: C₁₉H₂₈O₆S₃
• 分子量: 448.626
• InChiKey: AGZDSONTLWZDGH-XNQOWJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  169
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3S)-3-[(R)-hydroxy-[(6R,10S)-6-[(S)-hydroxy-[(3R)-4-oxothian-3-yl]methyl]-1,4-dioxa-8-thiaspiro[4.5]decan-10-yl]methyl]thian-4-one 在 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 144.0h， 生成 C₂₃H₃₆O₈S₃
  参考文献：
  名称：

  Asymmetric Synthesis of Hexapropionate Synthons by Sequential Enantiotopic Group Selective Enolization of Meso Diketones

  摘要：

  Meso 1,9-diketones (six to seven stereocenters) are readily obtained by stepwise or simultaneous two-directional aldol reactions of tetrahydro-4H-thiopyran-4-one with a thiopyran-derived aldehyde or dialdehyde. Enantioselective enolizations of these diketones with the lithium amide from (R, R)-bis(1-phenylethyl) amine occur with simultaneous kinetic resolution to give the mono-TMS enol ethers in > 90% yields (BORSM) and > 95% ee. The products are applicable to polypropionate synthesis.

  DOI：

  10.1021/ol060802k
• 作为产物：
  描述：

  (6R,10S)-1,4-dioxa-8-thiaspiro[4.5]decane-6,10-dicarboxaldehyde 、 四氢噻喃-4-酮 在 氯代二环己基硼烷 、 三乙胺 、 双氧水 作用下， 以 二氯甲烷 、 甲醇 、 水 为溶剂， 反应 4.17h， 以50%的产率得到(3S)-3-[(R)-hydroxy-[(6R,10S)-6-[(S)-hydroxy-[(3R)-4-oxothian-3-yl]methyl]-1,4-dioxa-8-thiaspiro[4.5]decan-10-yl]methyl]thian-4-one
  参考文献：
  名称：

  Asymmetric Synthesis of Hexapropionate Synthons by Sequential Enantiotopic Group Selective Enolization of Meso Diketones

  摘要：

  Meso 1,9-diketones (six to seven stereocenters) are readily obtained by stepwise or simultaneous two-directional aldol reactions of tetrahydro-4H-thiopyran-4-one with a thiopyran-derived aldehyde or dialdehyde. Enantioselective enolizations of these diketones with the lithium amide from (R, R)-bis(1-phenylethyl) amine occur with simultaneous kinetic resolution to give the mono-TMS enol ethers in > 90% yields (BORSM) and > 95% ee. The products are applicable to polypropionate synthesis.

  DOI：

  10.1021/ol060802k