(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3R,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentyl ester | 870192-70-4

• 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,3R,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentyl ester
• 英文别名: [(2S,3R,4S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4-dimethylpentyl] (2S)-3-phenylmethoxy-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 870192-70-4
• 化学式: C₃₁H₄₇NO₇Si
• 分子量: 573.802
• InChiKey: CLRMOHDDPUZXAH-NQPYUKKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  40
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3R,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentyl ester 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 palladium on activated charcoal sodium hypochlorite 、 氢气 、 sodium hexamethyldisilazane 、 碳酸氢钠 、 乙二胺 、 potassium bromide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.84h， 生成 (S)-2-Amino-3-benzyloxy-propionic acid (1R,2S)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-hexadecyl 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
• 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 咪唑 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 生成 (S)-3-Benzyloxy-2-benzyloxycarbonylamino-propionic acid (2S,3R,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-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

文献信息

• Synthesis of [13]-membered macrocyclic stevastelins via a transesterification reaction as the key step: total synthesis of stevastelin C3
  作者：Francisco Sarabia、Miguel García-Castro、Samy Chammaa

  DOI：10.1016/j.tetlet.2005.09.037

  日期：2005.11

  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.