(1S,2'S,5'S)-1-[5'-(tert-butyldiphenylsilanyloxymethyl)-2',5'-dihydrofuran-2'-yl]ethyl phenylselenocarbonate | 861902-81-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1S,2'S,5'S)-1-[5'-(tert-butyldiphenylsilanyloxymethyl)-2',5'-dihydrofuran-2'-yl]ethyl phenylselenocarbonate
• 英文别名: [(1S)-1-[(2S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,5-dihydrofuran-2-yl]ethyl] phenylselanylformate
• CAS: 861902-81-0
• 化学式: C₃₀H₃₄O₄SeSi
• 分子量: 565.643
• InChiKey: JUVCYKFDIXLUEA-QONNDPFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2'S,5'S)-1-[5'-(tert-butyldiphenylsilanyloxymethyl)-2',5'-dihydrofuran-2'-yl]ethyl phenylselenocarbonate 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 四丁基氟化铵 、 水 、 三正丁基氢锡 、 三乙胺 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 25.67h， 生成 (2S,3S,4S)-2-allyl-3-hydroxy-4-methyl-4-butanolide
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3S,4S)-3-hydroxy-4-methyl-2-tetradecyl-4-butanolide starting from 2,5-anhydro-d-mannitol

  摘要：

  A novel approach to natural beta-hydroxy-gamma-lactone 2 from 2,5-anhydro-D-mannitol (1) is described. The key reactions in this synthesis include stereoselective methylation of aldehyde 3 with lithium dimethylcuprate, an intramolecular radical cyclization of seleno carbonate 11 and an intermolecular cross-metathes is of 3-allyl-4-hydroxy-gamma-lactone 16 with 1-tridecene. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.059
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 吡啶 、 咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (1S,2'S,5'S)-1-[5'-(tert-butyldiphenylsilanyloxymethyl)-2',5'-dihydrofuran-2'-yl]ethyl phenylselenocarbonate
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3S,4S)-3-hydroxy-4-methyl-2-tetradecyl-4-butanolide starting from 2,5-anhydro-d-mannitol

  摘要：

  A novel approach to natural beta-hydroxy-gamma-lactone 2 from 2,5-anhydro-D-mannitol (1) is described. The key reactions in this synthesis include stereoselective methylation of aldehyde 3 with lithium dimethylcuprate, an intramolecular radical cyclization of seleno carbonate 11 and an intermolecular cross-metathes is of 3-allyl-4-hydroxy-gamma-lactone 16 with 1-tridecene. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.059

文献信息

• Stereoselective synthesis of (2R,3S,4S)-3-hydroxy-4-methyl-2-tetradecyl-4-butanolide starting from 2,5-anhydro-d-mannitol
  作者：Shunya Takahashi、Narihito Ogawa、Nobuo Sakairi、Tadashi Nakata

  DOI：10.1016/j.tet.2005.04.059

  日期：2005.7

  A novel approach to natural beta-hydroxy-gamma-lactone 2 from 2,5-anhydro-D-mannitol (1) is described. The key reactions in this synthesis include stereoselective methylation of aldehyde 3 with lithium dimethylcuprate, an intramolecular radical cyclization of seleno carbonate 11 and an intermolecular cross-metathes is of 3-allyl-4-hydroxy-gamma-lactone 16 with 1-tridecene. (c) 2005 Elsevier Ltd. All rights reserved.