(S)-3-(Bis-benzyloxy-phosphoryloxy)-2-(tert-butyl-dimethyl-silanyloxy)-propionic acid allyl ester | 370867-57-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (S)-3-(Bis-benzyloxy-phosphoryloxy)-2-(tert-butyl-dimethyl-silanyloxy)-propionic acid allyl ester
• 英文别名: prop-2-enyl (2S)-3-bis(phenylmethoxy)phosphoryloxy-2-[tert-butyl(dimethyl)silyl]oxypropanoate
• CAS: 370867-57-5
• 化学式: C₂₆H₃₇O₇PSi
• 分子量: 520.635
• InChiKey: YQQHIDHCZZVLOR-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-3-(Bis-benzyloxy-phosphoryloxy)-2-(tert-butyl-dimethyl-silanyloxy)-propionic acid allyl ester 在 四(三苯基膦)钯 吗啉 、 氰基磷酸二乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 dibenzyl [(2S)-2-[tert-butyl(dimethyl)silyl]oxy-3-[[(3S,6S,9S,12S,15S,18S,19R)-9,15-dibenzyl-3-[(2S)-butan-2-yl]-6-[[4-[tert-butyl(dimethyl)silyl]oxyphenyl]methyl]-12-(3-hydroxypropyl)-7,19-dimethyl-2,5,8,11,14,17-hexaoxo-1-oxa-4,7,10,13,16-pentazacyclononadec-18-yl]amino]-3-oxopropyl] phosphate
  参考文献：
  名称：

  Synthetic studies of the cyclic depsipeptides bearing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit. Total synthesis of the proposed structure of micropeptin T-20

  摘要：

  The first total synthesis of a cyclic depsipeptide possessing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit was successfully IN achieved in a convergent manner by the oxidative construction of the Ahp unit at the later stage of the synthesis. This synthetic work provides data indicating that the structure of the target Ahp-depsipeptide, micropeptin T-20. should be re-examined. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.009
• 作为产物：
  描述：

  allyl (S)-2,3-dihydroxypropanoate 在 2,6-二甲基吡啶 、 四氮唑 、 cerium(III) chloride 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 13.5h， 生成 (S)-3-(Bis-benzyloxy-phosphoryloxy)-2-(tert-butyl-dimethyl-silanyloxy)-propionic acid allyl ester
  参考文献：
  名称：

  Synthetic studies of the cyclic depsipeptides bearing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit. Total synthesis of the proposed structure of micropeptin T-20

  摘要：

  The first total synthesis of a cyclic depsipeptide possessing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit was successfully IN achieved in a convergent manner by the oxidative construction of the Ahp unit at the later stage of the synthesis. This synthetic work provides data indicating that the structure of the target Ahp-depsipeptide, micropeptin T-20. should be re-examined. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.009

文献信息

• Synthetic studies of micropeptin T-20, a novel 3-amino-6-hydroxy-2-piperidone (Ahp)-containing cyclic depsipeptide
  作者：Fumiaki Yokokawa、Akiko Inaizumi、Takayuki Shioiri

  DOI：10.1016/s0040-4039(01)01136-4

  日期：2001.8

  The synthetic studies of micropeptin T-20 including the late installation of the Ahp (3 -amino- 6-hydroxy-2-piperidone) residue through oxidation and cyclization of a homoserine to the requisite hemiaminal are described. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthetic studies of the cyclic depsipeptides bearing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit. Total synthesis of the proposed structure of micropeptin T-20
  作者：Fumiaki Yokokawa、Akiko Inaizumi、Takayuki Shioiri

  DOI：10.1016/j.tet.2004.12.009

  日期：2005.2

  The first total synthesis of a cyclic depsipeptide possessing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit was successfully IN achieved in a convergent manner by the oxidative construction of the Ahp unit at the later stage of the synthesis. This synthetic work provides data indicating that the structure of the target Ahp-depsipeptide, micropeptin T-20. should be re-examined. (C) 2004 Elsevier Ltd. All rights reserved.