(R)-4-[(2R,4R,6R)-6-((2R,6S)-6-Allyl-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 917017-62-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-4-[(2R,4R,6R)-6-((2R,6S)-6-Allyl-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4R)-4-[(2R,4R,6R)-4-[tert-butyl(diphenyl)silyl]oxy-6-[[(2R,6S)-4-methylidene-6-prop-2-enyloxan-2-yl]methyl]oxan-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 917017-62-0
• 化学式: C₄₁H₅₉NO₆Si
• 分子量: 690.008
• InChiKey: ZMJCYFLPHBHWMI-UVJUMCFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.92
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-4-[(2R,4R,6R)-6-((2R,6S)-6-Allyl-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 1,2-二溴四氯乙烷 、 四丁基氟化铵 、 碳酸氢钠 、 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.5h， 生成 tert-butyl (4R)-4-[(E)-2-[(1R,6E,9R,11R,12R,13S,16Z,19S,23R,25R,27R,31S)-27-[tert-butyl(diphenyl)silyl]oxy-12,31-dimethyl-21-methylidene-15-oxo-4,10,14,29,30-pentaoxa-32-azapentacyclo[23.3.1.12,5.19,13.119,23]dotriaconta-2,5(32),6,16-tetraen-11-yl]prop-1-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of the Phorboxazole A Macrolide by Ring-Closing Metathesis

  摘要：

  Described is a regio- and stereoselective ring-closing metathesis (RCM) to form the C2-C3 alkene of the macrolide-containing domain of phorboxazole A. This work demonstrates a dramatic effect of reaction solvent on RCM product (E/Z)-selectivity. This process offers an alternative assembly of the macrolide-containing domain of phorboxazole A, one of the most potent anticancer agents known.

  DOI：

  10.1021/ol0619922
• 作为产物：
  描述：

  (R)-4-{(2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(2R,6R)-4-methylene-6-(2-oxo-ethyl)-tetrahydro-pyran-2-ylmethyl]-tetrahydro-pyran-2-yl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 、 甲基三苯基溴化膦 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以131 mg的产率得到(R)-4-[(2R,4R,6R)-6-((2R,6S)-6-Allyl-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of the Phorboxazole A Macrolide by Ring-Closing Metathesis

  摘要：

  Described is a regio- and stereoselective ring-closing metathesis (RCM) to form the C2-C3 alkene of the macrolide-containing domain of phorboxazole A. This work demonstrates a dramatic effect of reaction solvent on RCM product (E/Z)-selectivity. This process offers an alternative assembly of the macrolide-containing domain of phorboxazole A, one of the most potent anticancer agents known.

  DOI：

  10.1021/ol0619922