(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester | 870192-69-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester
• CAS: 870192-69-1
• 化学式: C₂₅H₃₃NO₇
• 分子量: 459.54
• InChiKey: HNINCXOZGFEQCR-ZZTDLJEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  33.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  114.32
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 palladium on activated charcoal 咪唑 、 sodium hypochlorite 、 氢气 、 sodium hexamethyldisilazane 、 碳酸氢钠 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 乙二胺 、 三乙胺 、 N,N-二甲基甲酰胺 、 焦碳酸二乙酯 、 三氟乙酸 、 potassium bromide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.59h， 生成 (3S,6S,9S,12R,13R)-3-Benzyloxymethyl-6-((R)-1-hydroxy-ethyl)-9-isopropyl-12-methyl-13-((S)-1-methyl-pentadecyl)-1-oxa-4,7,10-triaza-cyclotridecane-2,5,8,11-tetraone
  参考文献：
  名称：

  Synthesis of [13]-membered macrocyclic stevastelins via a transesterification reaction as the key step: total synthesis of stevastelin C3

  摘要：

  A new synthesis of stevastelin C3 (3), a [13]-membered ring component of the stevastelin family, whose structure was recently revised, is reported. Initially, a macrolactonization approach was attempted to generate the [13]-membered macrolactone but this met with failure, so a translactonization reaction was tried to obtain the targeted stevastelin C3 (3) from the corresponding [15]-membered ring counterpart. Unfortunately, this strategy did not prove successful, and, consequently, we opted to undertake a transesterification reaction from 23, as a means to accommodate the requisite aminoacid moiety at the correct position, to obtain 24. From 24, and through intermediates 25-28, the acyclic precursor of the [13]-membered ring macrolactone, compound 30, was efficiently prepared. By utilizing the synthetic course developed by Chida, we took 30 forward and completed the total synthesis of stevastelin C3 (3). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.037
• 作为产物：
  描述：

  (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-diisopropoxy-2,4-dimethyl-pentyl ester 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以95%的产率得到(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester
  参考文献：
  名称：

  Synthesis of [13]-membered macrocyclic stevastelins via a transesterification reaction as the key step: total synthesis of stevastelin C3

  摘要：

  A new synthesis of stevastelin C3 (3), a [13]-membered ring component of the stevastelin family, whose structure was recently revised, is reported. Initially, a macrolactonization approach was attempted to generate the [13]-membered macrolactone but this met with failure, so a translactonization reaction was tried to obtain the targeted stevastelin C3 (3) from the corresponding [15]-membered ring counterpart. Unfortunately, this strategy did not prove successful, and, consequently, we opted to undertake a transesterification reaction from 23, as a means to accommodate the requisite aminoacid moiety at the correct position, to obtain 24. From 24, and through intermediates 25-28, the acyclic precursor of the [13]-membered ring macrolactone, compound 30, was efficiently prepared. By utilizing the synthetic course developed by Chida, we took 30 forward and completed the total synthesis of stevastelin C3 (3). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.037