(3S,5S)-7-(Benzyloxy)-3,5-dihydroxy-3,5-O-isopropylideneheptanal | 171524-05-3

• 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)-7-(Benzyloxy)-3,5-dihydroxy-3,5-O-isopropylideneheptanal
• 英文别名: 2-[(4S,6S)-2,2-dimethyl-6-(2-phenylmethoxyethyl)-1,3-dioxan-4-yl]acetaldehyde
• CAS: 171524-05-3
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: JOTKQOONLDHJNF-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,5S)-7-(Benzyloxy)-3,5-dihydroxy-3,5-O-isopropylideneheptanal 在 sodium tetrahydroborate 、 三丁基膦 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 24.0h， 生成 (3S,5S)-7-(Benzyloxy)-3,5-O-isopropylidene-1-(phenylthio)heptane-3,5-diol
  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：

  2-{(4R,6S)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-1,3-dioxan-4-yl}ethanol 在 sodium periodate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 生成 (3S,5S)-7-(Benzyloxy)-3,5-dihydroxy-3,5-O-isopropylideneheptanal
  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.