(2R,3S)-N-methoxy-N,2-dimethyl-5-phenylmethoxy-3-triethylsilyloxypentanamide | 157220-40-1

• 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: (2R,3S)-N-methoxy-N,2-dimethyl-5-phenylmethoxy-3-triethylsilyloxypentanamide
• CAS: 157220-40-1
• 化学式: C₂₁H₃₇NO₄Si
• 分子量: 395.615
• InChiKey: FZQXMVHOOVWJEQ-QUCCMNQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-N-methoxy-N,2-dimethyl-5-phenylmethoxy-3-triethylsilyloxypentanamide 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 potassium tert-butylate 、 二异丁基氢化铝 、 (-)-diethyl tartrate 作用下， 以 二氯甲烷 为溶剂， 生成 [3-((1S,2S)-4-Benzyloxy-1-methyl-2-triethylsilanyloxy-butyl)-oxiranyl]-methanol
  参考文献：
  名称：

  海洋来源的有效抗肿瘤物质Aplyronine A的合成研究：C21–C34段的立体合成

  摘要：

  丙烯醛A（1）的C21–C34片段2是一种有效的海洋来源抗肿瘤物质，是由酰亚胺11以25个步骤（总收率17％）对映选择性合成的。

  DOI：

  10.1016/0040-4039(94)88035-2
• 作为产物：
  描述：

  (4R,5S)-3-[(2R,3S)-3-hydroxy-2-methyl-5-phenylmethoxypentanoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one 在 咪唑 、 Me2AlN(Me)OMe 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3S)-N-methoxy-N,2-dimethyl-5-phenylmethoxy-3-triethylsilyloxypentanamide
  参考文献：
  名称：

  海洋来源的有效抗肿瘤物质Aplyronine A的合成研究：C21–C34段的立体合成

  摘要：

  丙烯醛A（1）的C21–C34片段2是一种有效的海洋来源抗肿瘤物质，是由酰亚胺11以25个步骤（总收率17％）对映选择性合成的。

  DOI：

  10.1016/0040-4039(94)88035-2

文献信息

• Studies of fragment assembly aldol reactions of chiral aldehydes and chiral methyl ketones: stereoselective synthesis of the C(13)–C(25) segment of scytophycin C
  作者：William R. Roush、Garrett J. Dilley

  DOI：10.1016/s0040-4039(99)00868-0

  日期：1999.7

  A highly stereoselective synthesis of the C(13)–C(25) fragment of scytophycin C is described, along with stereochemical studies of the key fragment assembly methyl ketone aldol reaction.

  描述了高度立体选择性合成胞藻霉素C的C（13）-C（25）片段，以及对关键片段组装甲基酮羟醛反应的立体化学研究。
• Aplyronine A, a Potent Antitumor Substance of Marine Origin, Aplyronines B and C, and Artificial Analogues:  Total Synthesis and Structure−Cytotoxicity Relationships
  作者：Hideo Kigoshi、Kiyotake Suenaga、Tsuyoshi Mutou、Takeshi Ishigaki、Toshiyuki Atsumi、Hiroyuki Ishiwata、Akira Sakakura、Takeshi Ogawa、Makoto Ojika、Kiyoyuki Yamada

  DOI：10.1021/jo9606113

  日期：1996.1.1

  The enantioselective total synthesis of aplyronine A (1), a potent antitumor substance of marine origin, was achieved by a convergent-approach Three segments 4, 5, and 6, corresponding to the C5-C11, C21-C27, and C28-C34 portions of aplyronine A (1), were prepared using:the Evans aldol reaction and the Sharpless epoxidation as key steps. The coupling reaction of 4 with iodide 7 followed by julia olefination with sulfone 8 gave the C5-C20 segment 9, while the julia coupling reaction between segments 5 and 6 provided the C21-C34 segment 10. Julia olefination between segments 9 and 10 and the subsequent four-carbon homologation reaction led to seco acid 83, which was converted into aplyronine A (1) by Yamaguchi lactonization followed by the introduction of two amino acids. The use of the [(3,4-dimethoxybenzyl)oxy]methyl group as a protecting group for the hydroxyl at C29 was crucial for this synthesis. The enantioselective synthesis of two natural congeners, aplyronines B (2) acid C (3), was also carried out using the intermediates for the synthesis of 1, which determined the absolute stereostructures of 2 and 3 unambiguously. To study the structure-cytotoxicity relationships of aplyronines, artificial analogues of 1 were synthesized and their cytotoxicities were evaluated: the trimethylserine moiety, two hydroxyl groups, and the side-chain portion in 1 turned out to be important in the potent cytotoxicity shown by 1. Biological studies with aplyronine A (1) showed that 1 inhibited polymerization of G-actin to F-actin and depolymerized F-actin to G-actin.