(2E,4S,5R)-5'-(tert-butyl(diphenyl)silyloxy)-2,4-dimethyl-2-hexen-1-ol | 1044263-54-8

• 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: (2E,4S,5R)-5'-(tert-butyl(diphenyl)silyloxy)-2,4-dimethyl-2-hexen-1-ol
• 英文别名: (E,4S,5R)-5-[tert-butyl(diphenyl)silyl]oxy-2,4-dimethylhex-2-en-1-ol
• CAS: 1044263-54-8
• 化学式: C₂₄H₃₄O₂Si
• 分子量: 382.618
• InChiKey: FLPXUECOLAMHDU-KUIMBALTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4S,5R)-5'-(tert-butyl(diphenyl)silyloxy)-2,4-dimethyl-2-hexen-1-ol 在 甲基三苯氧基碘磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (2E,4S,5R)-5'-(tert-butyl(diphenyl)silyloxy)-2,4-dimethyl-1-iodo-2-hexene
  参考文献：
  名称：

  Concise route to defined stereoisomers of the hydroxy acid of the chondramides

  摘要：

  The use of Kobayashi vinylogous aldol reaction in the reaction with acetaldehyde led to anti-aldol product 11. After reductive removal of the chiral auxiliary, the primary alcohol was converted to the allyliodide 14. This compound could be engaged in an Evans alkylation reaction, leading eventually to hydroxy acid 19. Inclusion of a Mitsunobu inversion reaction on the sequence starting with ent-11 led to hydroxy ester 30, featuring a 6,7-syn-configuration. These hydroxy acids should help to elucidate the correct stereostructure of the chondramide depsipeptides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.109
• 作为产物：
  描述：

  (4S,4'S,5'R,2'E)-3-[5'-(tert-butyl(diphenyl)silyloxy)-2',4'-dimethyl-2'-hexenoyl]-4-isopropyl-1,3-oxazolidin-2-one 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以89%的产率得到(2E,4S,5R)-5'-(tert-butyl(diphenyl)silyloxy)-2,4-dimethyl-2-hexen-1-ol
  参考文献：
  名称：

  Concise route to defined stereoisomers of the hydroxy acid of the chondramides

  摘要：

  The use of Kobayashi vinylogous aldol reaction in the reaction with acetaldehyde led to anti-aldol product 11. After reductive removal of the chiral auxiliary, the primary alcohol was converted to the allyliodide 14. This compound could be engaged in an Evans alkylation reaction, leading eventually to hydroxy acid 19. Inclusion of a Mitsunobu inversion reaction on the sequence starting with ent-11 led to hydroxy ester 30, featuring a 6,7-syn-configuration. These hydroxy acids should help to elucidate the correct stereostructure of the chondramide depsipeptides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.109