3R-(tert-butoxycarbonyl)-amino-3-(4-methoxyphenyl)-2S-propane-1-(tert-butyl dimethylsiloxy)-2-ol | 635313-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3R-(tert-butoxycarbonyl)-amino-3-(4-methoxyphenyl)-2S-propane-1-(tert-butyl dimethylsiloxy)-2-ol
• 英文别名: tert-butyl N-[(1R,2S)-3-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-1-(4-methoxyphenyl)propyl]carbamate
• CAS: 635313-42-7
• 化学式: C₂₁H₃₇NO₅Si
• 分子量: 411.614
• InChiKey: XKHBLVNSFCBQSN-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3R-(tert-butoxycarbonyl)-amino-3-(4-methoxyphenyl)-2S-propane-1-(tert-butyl dimethylsiloxy)-2-ol 在 lithium hydroxide 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 28.0h， 生成 (2R,3R)-(tert-butoxycarbonylamino)-3-(p-methoxyphenyl)-1,2-propanediol
  参考文献：
  名称：

  Stereoselective Synthesis of (−)-Cytoxazone and (+)-5-Epi-cytoxazone

  摘要：

  A novel, stereo selective synthesis of (-)-cytoxazone la and stereo-selective synthesis of (+)-5-epi-cytoxazone 1b were achieved via stereoselective Grignard addition of vinylmagnesium bromide on N-Boc aldehyde obtained from p-hydroxy-D-phenylglycine 2 followed by cyclization of N-Boc alcohol 6, ozonolysis and reduction to get (+)-5-epi-cytoxazone. Compound 6 underwent mitsunobu conditions, deprotection of ester followed by cyclization of N-Boc alcohol to get (-)-cytoxazone.

  DOI：

  10.1081/scc-120022181
• 作为产物：
  描述：

  (R)-methyl 2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate 在 咪唑 、 sodium tetrahydroborate 、 草酰氯 、 potassium carbonate 、 臭氧 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 3R-(tert-butoxycarbonyl)-amino-3-(4-methoxyphenyl)-2S-propane-1-(tert-butyl dimethylsiloxy)-2-ol
  参考文献：
  名称：

  Stereoselective Synthesis of (−)-Cytoxazone and (+)-5-Epi-cytoxazone

  摘要：

  A novel, stereo selective synthesis of (-)-cytoxazone la and stereo-selective synthesis of (+)-5-epi-cytoxazone 1b were achieved via stereoselective Grignard addition of vinylmagnesium bromide on N-Boc aldehyde obtained from p-hydroxy-D-phenylglycine 2 followed by cyclization of N-Boc alcohol 6, ozonolysis and reduction to get (+)-5-epi-cytoxazone. Compound 6 underwent mitsunobu conditions, deprotection of ester followed by cyclization of N-Boc alcohol to get (-)-cytoxazone.

  DOI：

  10.1081/scc-120022181

文献信息

• Stereoselective Synthesis of (−)-Cytoxazone and (+)-5-Epi-cytoxazone
  作者：A. Ravi Kumar、G. Bhaskar、A. Madhan、B. Venkateswara Rao

  DOI：10.1081/scc-120022181

  日期：2003.1.8

  A novel, stereo selective synthesis of (-)-cytoxazone la and stereo-selective synthesis of (+)-5-epi-cytoxazone 1b were achieved via stereoselective Grignard addition of vinylmagnesium bromide on N-Boc aldehyde obtained from p-hydroxy-D-phenylglycine 2 followed by cyclization of N-Boc alcohol 6, ozonolysis and reduction to get (+)-5-epi-cytoxazone. Compound 6 underwent mitsunobu conditions, deprotection of ester followed by cyclization of N-Boc alcohol to get (-)-cytoxazone.