(1S,2'R,3'R,4'R,5'R)-1-[3',4'-bis(tert-butyldimethylsilanyloxy)-5'-trityloxymethyltetrahydrofuran-2'-yl]ethanol | 861902-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (1S,2'R,3'R,4'R,5'R)-1-[3',4'-bis(tert-butyldimethylsilanyloxy)-5'-trityloxymethyltetrahydrofuran-2'-yl]ethanol
• 英文别名: (1S)-1-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(trityloxymethyl)oxolan-2-yl]ethanol
• CAS: 861902-74-1
• 化学式: C₃₈H₅₆O₅Si₂
• 分子量: 649.031
• InChiKey: NZDQUQRUKKTYMA-RXFHZEGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.92
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2'R,3'R,4'R,5'R)-1-[3',4'-bis(tert-butyldimethylsilanyloxy)-5'-trityloxymethyltetrahydrofuran-2'-yl]ethanol 在 四丁基氟化铵 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 99.0h， 生成 (1'S,2S,5S)-2-(1'-methoxymethoxyethyl)-5-trityloxymethyl-2,5-dihydrofuran
  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：

  甲基锂 、 (2S,3R,4R,5R)-3,4-di-tert-butyldimethylsilyloxy-2-formyl-5-(1-trityloxymethyl)tetrahydrofuran 在 copper(l) iodide 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (1S,2'R,3'R,4'R,5'R)-1-[3',4'-bis(tert-butyldimethylsilanyloxy)-5'-trityloxymethyltetrahydrofuran-2'-yl]ethanol 、 (1R,2'R,3'R,4'R,5'R)-1-[3',4'-bis(tert-butyldimethylsilanyloxy)-5'-trityloxymethyltetrahydrofuran-2'-yl]ethanol
  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.