(2S,4R)-2-(N-Benzyl-N-methylamino)-4-<oxy>-6-hepten-1-ol | 130459-42-6

• 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: (2S,4R)-2-(N-Benzyl-N-methylamino)-4-<oxy>-6-hepten-1-ol
• 英文别名: (2S,4R)-2-[benzyl(methyl)amino]-4-[tert-butyl(dimethyl)silyl]oxyhept-6-en-1-ol
• CAS: 130459-42-6
• 化学式: C₂₁H₃₇NO₂Si
• 分子量: 363.616
• InChiKey: QLJBCTWUBDHIOZ-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4R)-2-(N-Benzyl-N-methylamino)-4-<oxy>-6-hepten-1-ol 在 sodium hydroxide 、 四丁基氯化铵 作用下， 以 氯仿 为溶剂， 反应 0.75h， 生成 (4R,6R)-4-<oxy>-6,7-epoxyheptene
  参考文献：
  名称：

  Synthetic Studies on the Polyene Macrolide Antibiotics. Development of syn- and anti-1,3-Diol Subunits and Assembly of the Polyacetate Region of Amphotericin B

  摘要：

  The synthesis of syn- and anti-1,3-diol subunits from thiol ester oxazoline 4 has been described. The key features of these synthetic sequences include the stereodivergent allylation of an asymmetric beta-amino aldehyde (7) and the stereospecific transformation of a vicinal amino alcohol to an epoxide. The resultant diasteromeric silyl-protected epoxy alcohols (10s and 10a) serve as convenient precursors to the isomeric diol aldehyde derivatives 13, 13-ent, and 16. One of these fragments, compound 13, has been exploited in a highly convergent synthesis of the C1-C13 polyacetate segment of amphotericin B.

  DOI：

  10.1021/jo00129a019
• 作为产物：
  描述：

  (2R,4'S)-N'-Benzyl-2-<oxy>-1-(4'-oxazolidinyl)-4-pentene 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 0.08h， 以95%的产率得到(2S,4R)-2-(N-Benzyl-N-methylamino)-4-<oxy>-6-hepten-1-ol
  参考文献：
  名称：

  Synthetic Studies on the Polyene Macrolide Antibiotics. Development of syn- and anti-1,3-Diol Subunits and Assembly of the Polyacetate Region of Amphotericin B

  摘要：

  The synthesis of syn- and anti-1,3-diol subunits from thiol ester oxazoline 4 has been described. The key features of these synthetic sequences include the stereodivergent allylation of an asymmetric beta-amino aldehyde (7) and the stereospecific transformation of a vicinal amino alcohol to an epoxide. The resultant diasteromeric silyl-protected epoxy alcohols (10s and 10a) serve as convenient precursors to the isomeric diol aldehyde derivatives 13, 13-ent, and 16. One of these fragments, compound 13, has been exploited in a highly convergent synthesis of the C1-C13 polyacetate segment of amphotericin B.

  DOI：

  10.1021/jo00129a019

文献信息

• Studies toward the application of oxazolineepoxide equivalency in 1,3-asymmetric induction
  作者：Kenneth R. Overly、J.Michael Willams、Glenn J. McGarvey

  DOI：10.1016/s0040-4039(00)97679-2

  日期：1990.1
• OVERLY, KENNETH R.;WILLIAMS, J. MICHAEL;MCGARVEY, GLENN J., TETRAHEDRON LETT., 31,(1990) N2, C. 4573-4576
  作者：OVERLY, KENNETH R.、WILLIAMS, J. MICHAEL、MCGARVEY, GLENN J.

  DOI：——

  日期：——
• Synthetic Studies on the Polyene Macrolide Antibiotics. Development of syn- and anti-1,3-Diol Subunits and Assembly of the Polyacetate Region of Amphotericin B
  作者：Glenn J. McGarvey、Jeffrey A. Mathys、Kenneth J. Wilson、Kenneth R. Overly、Paul T. Buonora、P. Grant Spoors

  DOI：10.1021/jo00129a019

  日期：1995.12

  The synthesis of syn- and anti-1,3-diol subunits from thiol ester oxazoline 4 has been described. The key features of these synthetic sequences include the stereodivergent allylation of an asymmetric beta-amino aldehyde (7) and the stereospecific transformation of a vicinal amino alcohol to an epoxide. The resultant diasteromeric silyl-protected epoxy alcohols (10s and 10a) serve as convenient precursors to the isomeric diol aldehyde derivatives 13, 13-ent, and 16. One of these fragments, compound 13, has been exploited in a highly convergent synthesis of the C1-C13 polyacetate segment of amphotericin B.