(E)-(4S,5S,6R)-7-Benzyloxy-4,6-dimethyl-hept-2-ene-1,5-diol | 207226-62-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(4S,5S,6R)-7-Benzyloxy-4,6-dimethyl-hept-2-ene-1,5-diol
• 英文别名: (E,4S,5S,6R)-4,6-dimethyl-7-phenylmethoxyhept-2-ene-1,5-diol
• CAS: 207226-62-8
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: GPRTYQDDNOXWCJ-ICHHZDCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(4S,5S,6R)-7-Benzyloxy-4,6-dimethyl-hept-2-ene-1,5-diol 在 咪唑 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 75.5h， 生成 {(R)-2-[(4R,5R,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propoxy}-tert-butyl-diphenyl-silane
  参考文献：
  名称：

  Synthesis of Stereopentad Subunits of Zincophorin and Rifamycin-S through Use of Chiral Allenyltin Reagents

  摘要：

  The anti,anti adduct 3, from addition of the allenic stannane (P)-2 to the alpha-methyl-beta-OBn aldehyde (S)-1 promoted by SnCl4, was converted to the stereopentad 6 by a sequence involving reduction to the (E)-allylic alcohol with Red-Al, Sharpless asymmetric epoxidation, and addition of the higher-order methyl cyanocuprate to the derived epoxide 5. Stereopentad 6 was converted to the acetonide acetal 15, an intermediate in Danishefsky's synthesis of zincophorin. By a similar sequence, adduct ent-4 was converted, via diol 19, to stereopentad 22, an intermediate in Kishi's synthesis of rifamycin-S. An alternative route to diol 19 was achieved from the MOM-protected derivative 28 of epoxy diol 18.

  DOI：

  10.1021/jo980137w
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (4S,5S,6R)-7-benzyloxy-5-hydroxy-4,6-dimethyl-hept-2-ynyl ester 在 红铝 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以92%的产率得到(E)-(4S,5S,6R)-7-Benzyloxy-4,6-dimethyl-hept-2-ene-1,5-diol
  参考文献：
  名称：

  Synthesis of Stereopentad Subunits of Zincophorin and Rifamycin-S through Use of Chiral Allenyltin Reagents

  摘要：

  The anti,anti adduct 3, from addition of the allenic stannane (P)-2 to the alpha-methyl-beta-OBn aldehyde (S)-1 promoted by SnCl4, was converted to the stereopentad 6 by a sequence involving reduction to the (E)-allylic alcohol with Red-Al, Sharpless asymmetric epoxidation, and addition of the higher-order methyl cyanocuprate to the derived epoxide 5. Stereopentad 6 was converted to the acetonide acetal 15, an intermediate in Danishefsky's synthesis of zincophorin. By a similar sequence, adduct ent-4 was converted, via diol 19, to stereopentad 22, an intermediate in Kishi's synthesis of rifamycin-S. An alternative route to diol 19 was achieved from the MOM-protected derivative 28 of epoxy diol 18.

  DOI：

  10.1021/jo980137w