(2R,3R,4S,5S,6S)-1-Benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-2,4,6-trimethyl-heptane-3,5-diol | 207226-45-7

• 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: (2R,3R,4S,5S,6S)-1-Benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-2,4,6-trimethyl-heptane-3,5-diol
• 英文别名: (2R,3R,4S,5S,6S)-1-[tert-butyl(diphenyl)silyl]oxy-2,4,6-trimethyl-7-phenylmethoxyheptane-3,5-diol
• CAS: 207226-45-7
• 化学式: C₃₃H₄₆O₄Si
• 分子量: 534.811
• InChiKey: SKBVPTXCOZVIJI-OMIYMPEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S,6S)-1-Benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-2,4,6-trimethyl-heptane-3,5-diol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 Angstroem MS 、 camphor-10-sulfonic acid 、 氢气 、 magnesium 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 45.41h， 生成
  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：

  (2S,3S,4S)-1-Benzyloxy-4-((2S,3R)-3-hydroxymethyl-oxiranyl)-2-methyl-pentan-3-ol 在 咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.5h， 生成 (2R,3R,4S,5S,6S)-1-Benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-2,4,6-trimethyl-heptane-3,5-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

文献信息

• Synthesis of Stereopentad Subunits of Zincophorin and Rifamycin-S through Use of Chiral Allenyltin Reagents
  作者：James A. Marshall、Michael R. Palovich

  DOI：10.1021/jo980137w

  日期：1998.5.1

  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.