(3S,5R,7R)-5-O-(4-methoxybenzyl)-7-O-tert-butyldimethylsilyl-1-(4-tert-butyldimethylsilyloxyphenyl)icosane-3,5,7-triol | 1025446-84-7

• 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: (3S,5R,7R)-5-O-(4-methoxybenzyl)-7-O-tert-butyldimethylsilyl-1-(4-tert-butyldimethylsilyloxyphenyl)icosane-3,5,7-triol
• 英文别名: (3S,5R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-1-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-5-[(4-methoxyphenyl)methoxy]icosan-3-ol
• CAS: 1025446-84-7
• 化学式: C₄₆H₈₂O₅Si₂
• 分子量: 771.325
• InChiKey: BDYZLPWVDAKDLA-JJKLPUCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.83
• 重原子数：
  53
• 可旋转键数：
  29
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,5R,7R)-5-O-(4-methoxybenzyl)-7-O-tert-butyldimethylsilyl-1-(4-tert-butyldimethylsilyloxyphenyl)icosane-3,5,7-triol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以95%的产率得到(5S,7R)-5-O-(4-methoxybenzyl)-7-(tert-butyldimethylsilyloxy)-1-(4-tert-butyldimethylsilyloxyphenyl)icosan-3-one
  参考文献：
  名称：

  A Carbohydrate-Based Approach for the Total Synthesis of Aculeatin D and 6-epi-Aculeatin D

  摘要：

  A concise approach for the total synthesis of aculeatin D and 6-epi-aculeatin D employing differentially protected anti,anti-1,3,5-triol alkyne prepared from alpha-D-glucoheptonic-gamma-lactone derivative is documented. Phenol protecting group manipulation for selective O-debenzylation during the hydrogenation of the diyne intermediate and one-pot phenolic oxidation with concomitant spiroketalization highlight the accomplished total synthesis.

  DOI：

  10.1021/jo800026n
• 作为产物：
  描述：

  tert-butyl-[4-[(3R,5R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-5-[(4-methoxyphenyl)methoxy]-3-phenylmethoxyicosa-1,9-diynyl]phenoxy]-dimethylsilane 在 镍 氢气 作用下， 以 乙醇 为溶剂， 55.0 ℃ 、137.9 kPa 条件下， 反应 18.0h， 以88%的产率得到(3S,5R,7R)-5-O-(4-methoxybenzyl)-7-O-tert-butyldimethylsilyl-1-(4-tert-butyldimethylsilyloxyphenyl)icosane-3,5,7-triol
  参考文献：
  名称：

  A Carbohydrate-Based Approach for the Total Synthesis of Aculeatin D and 6-epi-Aculeatin D

  摘要：

  A concise approach for the total synthesis of aculeatin D and 6-epi-aculeatin D employing differentially protected anti,anti-1,3,5-triol alkyne prepared from alpha-D-glucoheptonic-gamma-lactone derivative is documented. Phenol protecting group manipulation for selective O-debenzylation during the hydrogenation of the diyne intermediate and one-pot phenolic oxidation with concomitant spiroketalization highlight the accomplished total synthesis.

  DOI：

  10.1021/jo800026n

文献信息

• A Carbohydrate-Based Approach for the Total Synthesis of Aculeatin D and 6-<i>epi</i>-Aculeatin D
  作者：C. V. Ramana、Burgula Srinivas

  DOI：10.1021/jo800026n

  日期：2008.5.1

  A concise approach for the total synthesis of aculeatin D and 6-epi-aculeatin D employing differentially protected anti,anti-1,3,5-triol alkyne prepared from alpha-D-glucoheptonic-gamma-lactone derivative is documented. Phenol protecting group manipulation for selective O-debenzylation during the hydrogenation of the diyne intermediate and one-pot phenolic oxidation with concomitant spiroketalization highlight the accomplished total synthesis.