(2S,4E,6S,7R)-tert-butyl 7-{[tert-butyl(diphenyl)silyl]oxy}-2,4,6-trimethyloct-4-enoate | 1044263-58-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,4E,6S,7R)-tert-butyl 7-{[tert-butyl(diphenyl)silyl]oxy}-2,4,6-trimethyloct-4-enoate
• CAS: 1044263-58-2
• 化学式: C₃₁H₄₆O₃Si
• 分子量: 494.79
• InChiKey: UXPNKTKYQTZNMT-NRPIHIQOSA-N

反应信息

• 作为反应物：
  描述：

  (2S,4E,6S,7R)-tert-butyl 7-{[tert-butyl(diphenyl)silyl]oxy}-2,4,6-trimethyloct-4-enoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以82%的产率得到(2S,4E,6S,7R)-tert-butyl 7-hydroxy-2,4,6-trimethyloct-4-enoate
  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：

  (2S,4E,6S,7R)-7-{[tert-butyl(diphenyl)silyl]oxy}-2,4,6-trimethyloct-4-enoyl chloride 、 叔丁醇 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以0.242 g的产率得到(2S,4E,6S,7R)-tert-butyl 7-{[tert-butyl(diphenyl)silyl]oxy}-2,4,6-trimethyloct-4-enoate
  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