(3S,5R)-3-((S)-(methoxymethoxy)((R)-1,4-dioxa-8-thiaspiro[4.5]decan-6-yl)methyl)-5-((R)-(methoxymethoxy)((S)-1,4-dioxa-8-thiaspiro[4.5]decan-6-yl)methyl)tetrahydro-2H-thiopyran | 898826-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,5R)-3-((S)-(methoxymethoxy)((R)-1,4-dioxa-8-thiaspiro[4.5]decan-6-yl)methyl)-5-((R)-(methoxymethoxy)((S)-1,4-dioxa-8-thiaspiro[4.5]decan-6-yl)methyl)tetrahydro-2H-thiopyran
• CAS: 898826-12-5
• 化学式: C₂₅H₄₂O₈S₃
• 分子量: 566.802
• InChiKey: KEYPTSCPBGDWQN-WCXQMFAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (3S,5R)-3-((S)-(methoxymethoxy)((R)-1,4-dioxa-8-thiaspiro[4.5]decan-6-yl)methyl)-5-((R)-(methoxymethoxy)((S)-1,4-dioxa-8-thiaspiro[4.5]decan-6-yl)methyl)tetrahydro-2H-thiopyran 在 silica gel 、 三氯化铁 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以72%的产率得到(S)-3-((R)-hydroxy((3R,5S)-5-((S)-hydroxy((R)-4-oxotetrahydro-2H-thiopyran-3-yl)methyl)tetrahydro-2H-thiopyran-3-yl)methyl)tetrahydro-4H-thiopyran-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
• 作为产物：
  描述：

  (+/-)-(3S,5R)-3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(methoxymethoxy)methyl]-5-[(S)-(6R)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(methoxymethoxy)methyl]tetrahydro-4H-thiopyran-4-one 在 咪唑 、 sodium tetrahydroborate 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.25h， 生成 (3S,5R)-3-((S)-(methoxymethoxy)((R)-1,4-dioxa-8-thiaspiro[4.5]decan-6-yl)methyl)-5-((R)-(methoxymethoxy)((S)-1,4-dioxa-8-thiaspiro[4.5]decan-6-yl)methyl)tetrahydro-2H-thiopyran
  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