(6S,10R)-6-[(R)-Methoxymethoxy-((S)-4-trimethylsilanyloxy-3,6-dihydro-2H-thiopyran-3-yl)-methyl]-10-[(S)-methoxymethoxy-((R)-4-trimethylsilanyloxy-3,6-dihydro-2H-thiopyran-3-yl)-methyl]-1,4-dioxa-8-thia-spiro[4.5]decane | 898826-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (6S,10R)-6-[(R)-Methoxymethoxy-((S)-4-trimethylsilanyloxy-3,6-dihydro-2H-thiopyran-3-yl)-methyl]-10-[(S)-methoxymethoxy-((R)-4-trimethylsilanyloxy-3,6-dihydro-2H-thiopyran-3-yl)-methyl]-1,4-dioxa-8-thia-spiro[4.5]decane
• CAS: 898826-05-6
• 化学式: C₂₉H₅₂O₈S₃Si₂
• 分子量: 681.096
• InChiKey: KSPZNTNEZPINHZ-JDAMOXFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (6S,10R)-6-[(R)-Methoxymethoxy-((S)-4-trimethylsilanyloxy-3,6-dihydro-2H-thiopyran-3-yl)-methyl]-10-[(S)-methoxymethoxy-((R)-4-trimethylsilanyloxy-3,6-dihydro-2H-thiopyran-3-yl)-methyl]-1,4-dioxa-8-thia-spiro[4.5]decane 在 氢氟酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以93%的产率得到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：

  C₂₃H₃₆O₈S₃ 、 三甲基氯硅烷 在 lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以17%的产率得到(6S,10R)-6-[(R)-Methoxymethoxy-((S)-4-trimethylsilanyloxy-3,6-dihydro-2H-thiopyran-3-yl)-methyl]-10-[(S)-methoxymethoxy-((R)-4-trimethylsilanyloxy-3,6-dihydro-2H-thiopyran-3-yl)-methyl]-1,4-dioxa-8-thia-spiro[4.5]decane
  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