(3S,5S,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-oxo-13-tetradecene-3,5,9,11-tetrol | 171524-10-0

• 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: (3S,5S,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-oxo-13-tetradecene-3,5,9,11-tetrol
• 英文别名: 3-[(4R,6S)-2,2-dimethyl-6-(2-phenylmethoxyethyl)-1,3-dioxan-4-yl]-1-[(4R,6R)-2,2-dimethyl-6-prop-2-enyl-1,3-dioxan-4-yl]propan-1-one
• CAS: 171524-10-0
• 化学式: C₂₇H₄₀O₆
• 分子量: 460.611
• InChiKey: CAPMVMIEVNFGMW-AGDMDRQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,5S,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-oxo-13-tetradecene-3,5,9,11-tetrol 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-13-tetradecene-3,5,8,9,11-pentol
  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：

  (2S,4R)-2-(N-Benzylamino)-4-<oxy>-6-hepten-1-ol 在 咪唑 、 盐酸 、 sodium hydroxide 、 四氧化锇 、 四丁基氯化铵 、 碘 、 叔丁基锂 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 N-甲基吗啉氧化物 、 三苯基膦 、 sodium sulfite 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 氯仿 、 水 、 甲苯 、 叔丁醇 、 苯 为溶剂， 反应 20.24h， 生成 (3S,5S,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-oxo-13-tetradecene-3,5,9,11-tetrol
  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

• 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.