(2R,4S)-2,4-O-Isopropylidene-1-(phenylthio)-6-heptene-2-ol | 171598-92-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2R,4S)-2,4-O-Isopropylidene-1-(phenylthio)-6-heptene-2-ol
• 英文别名: (4R,6S)-2,2-dimethyl-4-(phenylsulfanylmethyl)-6-prop-2-enyl-1,3-dioxane
• CAS: 171598-92-8
• 化学式: C₁₆H₂₂O₂S
• 分子量: 278.415
• InChiKey: NQQRWRITLXPVDV-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4S)-2,4-O-Isopropylidene-1-(phenylthio)-6-heptene-2-ol 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 以90%的产率得到(2R,4S)-2,4-O-Isopropylidene-1-(phenylsulfinyl)-6-heptene-2-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
• 作为产物：
  描述：

  (2S,4'S)-2-(N-Benzylamino)-4-<oxy>-6-hepten-1-ol 在 盐酸 、 sodium hydroxide 、 四丁基氯化铵 、 二异丁基氢化铝 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 氯仿 、 水 、 叔丁醇 、 苯 为溶剂， 反应 3.49h， 生成 (2R,4S)-2,4-O-Isopropylidene-1-(phenylthio)-6-heptene-2-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

• 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.