N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-L-serine (1R,2S)-1-[(1S)-2-[(1,1-dimethylethyl)dimethylsilyl]oxy-1-methylethyl]-2-methylhexadecyl ester | 870192-75-9

• 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: N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-L-serine (1R,2S)-1-[(1S)-2-[(1,1-dimethylethyl)dimethylsilyl]oxy-1-methylethyl]-2-methylhexadecyl ester
• 英文别名: [(2S,3R,4S)-1-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethyloctadecan-3-yl] (2S)-2-[[(2S,3R)-3-hydroxy-2-[[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]butanoyl]amino]-3-phenylmethoxypropanoate
• CAS: 870192-75-9
• 化学式: C₅₀H₉₁N₃O₉Si
• 分子量: 906.373
• InChiKey: GJLZIQFHDCHIJR-FKXPPKDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  63
• 可旋转键数：
  35
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  162
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-L-serine (1R,2S)-1-[(1S)-2-[(1,1-dimethylethyl)dimethylsilyl]oxy-1-methylethyl]-2-methylhexadecyl ester 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以90%的产率得到N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-L-serine (1R,2S)-1-[(1S)-2-hydroxy-1-methylethyl]-2-methylhexadecyl 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：

  N-(tert-butoxycarbonyl)valine-O-benzyl-L-threonine benzyl ester 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-L-serine (1R,2S)-1-[(1S)-2-[(1,1-dimethylethyl)dimethylsilyl]oxy-1-methylethyl]-2-methylhexadecyl ester
  参考文献：
  名称：

  Stevastelins 的全合成：Stevastelin B 和 B3 的结构确认，以及 Stevastelin C3 的结构修正

  摘要：

  描述了 stevastelin B、B3、C3 和 stevastelin C3 的 5-脱氧衍生物、从 L-quebrachitol 开始的新型环状缩酚和氨基酸的全合成。将两个甲基立体选择性地引入 L-栎醇，然后通过 Baeyer-Villiger 反应对环己烷环进行区域选择性裂解，有效地提供了甜菊素的脂肪酸部分。肽的引入和随后的大环内酰胺化产生了stevastelin B。Stevastelin C3 和B3 也通过类似的方式合成。合成 stevastelins 与天然化合物的直接比较表明，合成 stevastelins B 和 B3 与天然产物相同，证实了所提出的结构。然而，发现合成的 stevastelin C3 与天然产物不同。为了阐明 stevastelin C3 的结构，进行了天然产物的降解，以表明天然产物可能是所提出结构的 5-脱氧衍生物。因此，制备了脂肪酸部分的5-脱氧衍生物并将其转化为大环。合成的

  DOI：

  10.1246/bcsj.79.921

文献信息

• Total Synthesis of Stevastelins: Structure Confirmation of Stevastelins B and B3, and Structure Revision of Stevastelin C3
  作者：Kazuo Kurosawa、Keigo Matsuura、Toshihiko Nagase、Noritaka Chida

  DOI：10.1246/bcsj.79.921

  日期：2006.6

  peptide and subsequent macrolactamization gave stevastelin B. Stevastelins C3 and B3 were also synthesized by a similar way. The direct comparison of synthetic stevastelins with natural compounds revealed that the synthetic stevastelins B and B3 are identical to the natural products, confirming the proposed structures. However, the synthetic stevastelin C3 was found to not be identical with the natural

  描述了 stevastelin B、B3、C3 和 stevastelin C3 的 5-脱氧衍生物、从 L-quebrachitol 开始的新型环状缩酚和氨基酸的全合成。将两个甲基立体选择性地引入 L-栎醇，然后通过 Baeyer-Villiger 反应对环己烷环进行区域选择性裂解，有效地提供了甜菊素的脂肪酸部分。肽的引入和随后的大环内酰胺化产生了stevastelin B。Stevastelin C3 和B3 也通过类似的方式合成。合成 stevastelins 与天然化合物的直接比较表明，合成 stevastelins B 和 B3 与天然产物相同，证实了所提出的结构。然而，发现合成的 stevastelin C3 与天然产物不同。为了阐明 stevastelin C3 的结构，进行了天然产物的降解，以表明天然产物可能是所提出结构的 5-脱氧衍生物。因此，制备了脂肪酸部分的5-脱氧衍生物并将其转化为大环。合成的
• 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.