Benzoic acid (2R,3S)-5-(tert-butyl-diphenyl-silanyloxy)-2-[(2'-methoxymethoxymethyl-[2,4']bioxazolyl-4-carbonyl)-amino]-3-methyl-pentyl ester | 477332-10-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid (2R,3S)-5-(tert-butyl-diphenyl-silanyloxy)-2-[(2'-methoxymethoxymethyl-[2,4']bioxazolyl-4-carbonyl)-amino]-3-methyl-pentyl ester
• 英文别名: [(2R,3S)-5-[tert-butyl(diphenyl)silyl]oxy-2-[[2-[2-(methoxymethoxymethyl)-1,3-oxazol-4-yl]-1,3-oxazole-4-carbonyl]amino]-3-methylpentyl] benzoate
• CAS: 477332-10-8
• 化学式: C₃₉H₄₅N₃O₈Si
• 分子量: 711.887
• InChiKey: IPBGWZKMZPUQGC-IUDBTDONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  51
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3S)-5-(tert-butyl-diphenyl-silanyloxy)-2-[(2'-methoxymethoxymethyl-[2,4']bioxazolyl-4-carbonyl)-amino]-3-methyl-pentyl ester 在 2,6-二甲基吡啶 、 甲醇 、 dibromotetrachloroethane 、 四丁基氟化铵 、 potassium carbonate 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-3-(2''-Methoxymethoxymethyl-[2,4';2',4'']teroxazol-4-yl)-butan-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of a C1C19 fragment of ulapualide A

  摘要：

  The stereocontrolled synthesis of a C1-C19 fragment of ulapualide A has been accomplished. The C3 hydroxyl-bearing stereocenter was established by Jacobsen's hydrolytic kinetic resolution (HKR) of a terminal epoxide. while the C9 methyl stereocenter was introduced through an asymmetric crotylation using chiral organosilane (S)-7. Union of the C1-C6 and the C7-C19 fragments by a Kishi-Nozaki coupling, followed by oxidation and conjugate addition of hydride completed the preparation of the fragment. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01553-8
• 作为产物：
  描述：

  Benzoic acid (2R,3S)-2-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentyl ester 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Benzoic acid (2R,3S)-5-(tert-butyl-diphenyl-silanyloxy)-2-[(2'-methoxymethoxymethyl-[2,4']bioxazolyl-4-carbonyl)-amino]-3-methyl-pentyl ester
  参考文献：
  名称：

  Asymmetric synthesis of a C1C19 fragment of ulapualide A

  摘要：

  The stereocontrolled synthesis of a C1-C19 fragment of ulapualide A has been accomplished. The C3 hydroxyl-bearing stereocenter was established by Jacobsen's hydrolytic kinetic resolution (HKR) of a terminal epoxide. while the C9 methyl stereocenter was introduced through an asymmetric crotylation using chiral organosilane (S)-7. Union of the C1-C6 and the C7-C19 fragments by a Kishi-Nozaki coupling, followed by oxidation and conjugate addition of hydride completed the preparation of the fragment. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01553-8