(S)-3-((R)-{(3R,4S,5R)-5-[(R)-((3S,4R)-4-Hydroxy-tetrahydro-thiopyran-3-yl)-methoxy-methyl]-4-methoxy-tetrahydro-thiopyran-3-yl}-methoxy-methyl)-tetrahydro-thiopyran-4-one | 898826-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (S)-3-((R)-{(3R,4S,5R)-5-[(R)-((3S,4R)-4-Hydroxy-tetrahydro-thiopyran-3-yl)-methoxy-methyl]-4-methoxy-tetrahydro-thiopyran-3-yl}-methoxy-methyl)-tetrahydro-thiopyran-4-one
• 英文别名: (3S)-3-[(R)-[(3R,4S,5R)-5-[(R)-[(3S,4R)-4-hydroxythian-3-yl]-methoxymethyl]-4-methoxythian-3-yl]-methoxymethyl]thian-4-one
• CAS: 898826-06-7
• 化学式: C₂₀H₃₄O₅S₃
• 分子量: 450.685
• InChiKey: IHNKCRHWXOMRRZ-KENULNKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-3-((R)-{(3R,4S,5R)-5-[(R)-((3S,4R)-4-Hydroxy-tetrahydro-thiopyran-3-yl)-methoxy-methyl]-4-methoxy-tetrahydro-thiopyran-3-yl}-methoxy-methyl)-tetrahydro-thiopyran-4-one 在 sodium hypophosphite 、 sodium acetate 、 镍 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 8.5h， 生成 (4R,5S,6S,7S,8R,9R,10S)-5,7,9-trimethoxy-4,6,8,10-tetramethyltridecane-3,11-dione
  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(hydroxy)methyl]-5-[(S)-(6R)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(hydroxy)methyl]tetrahydro-4H-thiopyran-4-one 在 amberlyst-15 、 potassium hydride 、 L-Selectride 、 二异丁基氢化铝 、 lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 、 甲苯 为溶剂， 反应 15.92h， 生成 (S)-3-((R)-{(3R,4S,5R)-5-[(R)-((3S,4R)-4-Hydroxy-tetrahydro-thiopyran-3-yl)-methoxy-methyl]-4-methoxy-tetrahydro-thiopyran-3-yl}-methoxy-methyl)-tetrahydro-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