[(2R,3R)-3-((1R,2R,3S,4R,5R,6R,7R)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol | 177766-85-7

• 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,3R)-3-((1R,2R,3S,4R,5R,6R,7R)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol
• 英文别名: [(2R,3R)-3-[(2R,3R,4S,5R,6R,7R,8R)-4,6,8-trimethyl-9-phenylmethoxy-3,5,7-tris(triethylsilyloxy)nonan-2-yl]oxiran-2-yl]methanol
• CAS: 177766-85-7
• 化学式: C₄₀H₇₈O₆Si₃
• 分子量: 739.312
• InChiKey: ZKCXWYDIXUYUBK-RVMLVGHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.68
• 重原子数：
  49
• 可旋转键数：
  27
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R,3R)-3-((1R,2R,3S,4R,5R,6R,7R)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol 在 Pd-BaSO₄ 草酰氯 、 四丁基氟化铵 、 水 、 氢气 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 (E)-(S)-4-((4S,5R,6R)-6-{(S)-1-[(4R,5R,6R)-6-((R)-2-Hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-2-methyl-pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Tandem synthesis of polypropionate chains–highly stereoselective synthesis of the ansa chain of streptovaricin U and protostreptovaricins based on stereospecific methylation of γ,δ-epoxy acrylates by trimethylaluminium

  摘要：

  The highly stereoselective synthesis of the ansa chain segment 23 of streptovaricin U and protostreptovaricins (I and II) is achieved by stereospecific methylation of gamma,delta-epoxy acrylates with trimethylaluminium.

  DOI：

  10.1039/cc9960001027
• 作为产物：
  描述：

  (E)-(4R,5R,6S,7S,8R,9R,10R)-11-Benzyloxy-4,6,8,10-tetramethyl-5,7,9-tris-triethylsilanyloxy-undec-2-enoic acid ethyl ester 在 二异丁基氢化铝 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 [(2R,3R)-3-((1R,2R,3S,4R,5R,6R,7R)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol
  参考文献：
  名称：

  Tandem synthesis of polypropionate chains–highly stereoselective synthesis of the ansa chain of streptovaricin U and protostreptovaricins based on stereospecific methylation of γ,δ-epoxy acrylates by trimethylaluminium

  摘要：

  The highly stereoselective synthesis of the ansa chain segment 23 of streptovaricin U and protostreptovaricins (I and II) is achieved by stereospecific methylation of gamma,delta-epoxy acrylates with trimethylaluminium.

  DOI：

  10.1039/cc9960001027

文献信息

• Highly stereoselective epoxidation of a 4-methyl-5-(triethylsilyl)oxyallyl alcohol system with m-chloroperoxybenzoic acid
  作者：Kimiyuki Maruyama、Masato Ueda、Shinobu Sasaki、Yasuhiro Iwata、Masahiro Miyazawa、Masaaki Miyashita

  DOI：10.1016/s0040-4039(98)00804-1

  日期：1998.6

  Epoxidation of 4-methyl-5-(triethylsilyl)oxyallyl alcohol system with m-chloroperoxybenzoic acid (MCPBA) has been found to occur highly stereoselectively and in high yields from the opposite side of the C5 triethylsiloxy group regardless of the stereochemistry of an adjacent methyl group.

  与4-甲基-5-（三乙基甲硅烷）氧烯丙基醇体系的环氧化米氯过氧苯甲酸（MCPBA）已经发现，发生立体选择性的高度和从C的相对侧高的产率5三乙基甲硅烷基而不管相邻的立体化学的甲基。
• Tandem synthesis of polypropionate chains–highly stereoselective synthesis of the ansa chain of streptovaricin U and protostreptovaricins based on stereospecific methylation of γ,δ-epoxy acrylates by trimethylaluminium
  作者：Masaaki Miyashita、Tomonori Shiratani、Katsumi Kawamine、Susumi Hatakeyama、Hiroshi Irie

  DOI：10.1039/cc9960001027

  日期：——

  The highly stereoselective synthesis of the ansa chain segment 23 of streptovaricin U and protostreptovaricins (I and II) is achieved by stereospecific methylation of gamma,delta-epoxy acrylates with trimethylaluminium.