(2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one | 851592-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one
• CAS: 851592-80-8
• 化学式: C₂₈H₃₈O₄Si
• 分子量: 466.693
• InChiKey: XNZYYILBAVFJFK-AEAGWUPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以94%的产率得到(2S,3R,4R,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-ol
  参考文献：
  名称：

  Enantioselective Synthesis of the C18−C25 Segment of Lasonolide A by an Oxonia-Cope Prins Cascade

  摘要：

  A 2-oxonia-Cope Prins cascade was developed that led to a facile and stereoselective synthesis of the C18-C25 segment of lasonolide A. The strategy nicely handles the introduction of the quaternary center in the tetrahydropyran ring, and all of the stereogenic centers in the product arise from a single stereocenter introduced in a catalytic enantioselective reaction.

  DOI：

  10.1021/ol050270s
• 作为产物：
  描述：

  Acetic acid 1-{(S)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyloxy}-2-(5-methyl-6H-[1,3]dioxin-4-yl)-ethyl ester 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到(2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one
  参考文献：
  名称：

  Enantioselective Synthesis of the C18−C25 Segment of Lasonolide A by an Oxonia-Cope Prins Cascade

  摘要：

  A 2-oxonia-Cope Prins cascade was developed that led to a facile and stereoselective synthesis of the C18-C25 segment of lasonolide A. The strategy nicely handles the introduction of the quaternary center in the tetrahydropyran ring, and all of the stereogenic centers in the product arise from a single stereocenter introduced in a catalytic enantioselective reaction.

  DOI：

  10.1021/ol050270s