methyl (3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-4-(p-methoxybenzyloxy)hept-6-enoate | 916154-06-8

• 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: methyl (3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-4-(p-methoxybenzyloxy)hept-6-enoate
• 英文别名: methyl (3R,4R,5S)-3-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-4-[(4-methoxyphenyl)methoxy]hept-6-enoate
• CAS: 916154-06-8
• 化学式: C₂₂H₃₆O₆Si
• 分子量: 424.61
• InChiKey: NOEHBKXIIPTZGS-QKNQBKEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-4-(p-methoxybenzyloxy)hept-6-enoate 在 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 41.5h， 生成 (S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-(p-methoxybenzyloxy)hept-6-enoate
  参考文献：
  名称：

  The First Total Synthesis of Sporiolide A

  摘要：

  The first total synthesis of the natural cytotoxic agent sporiolide A has been accomplished from D-glucal in 16 steps with 6.1% overall yield. Carbohydrates were applied as the chiral templates to manipulate the absolute configuration during the synthesis. Pyridinium chlorochromate (PCC)-promoted transformation of the cyclic enol-ether to lactone, followed by Yamaguchi esterification and intramolecular ring closure metathesis, greatly facilitates synthesis of the target compound.

  DOI：

  10.1021/jo0615504
• 作为产物：
  描述：

  3-O-tert-butyldimethylsilyl-4-O-(4-methoxybenzyl)-D-glucal 在 草酰氯 、 silica gel 、 二甲基亚砜 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.5h， 生成 methyl (3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-4-(p-methoxybenzyloxy)hept-6-enoate
  参考文献：
  名称：

  The First Total Synthesis of Sporiolide A

  摘要：

  The first total synthesis of the natural cytotoxic agent sporiolide A has been accomplished from D-glucal in 16 steps with 6.1% overall yield. Carbohydrates were applied as the chiral templates to manipulate the absolute configuration during the synthesis. Pyridinium chlorochromate (PCC)-promoted transformation of the cyclic enol-ether to lactone, followed by Yamaguchi esterification and intramolecular ring closure metathesis, greatly facilitates synthesis of the target compound.

  DOI：

  10.1021/jo0615504

文献信息

• The First Total Synthesis of Sporiolide A
  作者：Yuguo Du、Qi Chen、Robert J. Linhardt

  DOI：10.1021/jo0615504

  日期：2006.10.1

  The first total synthesis of the natural cytotoxic agent sporiolide A has been accomplished from D-glucal in 16 steps with 6.1% overall yield. Carbohydrates were applied as the chiral templates to manipulate the absolute configuration during the synthesis. Pyridinium chlorochromate (PCC)-promoted transformation of the cyclic enol-ether to lactone, followed by Yamaguchi esterification and intramolecular ring closure metathesis, greatly facilitates synthesis of the target compound.