(3S,4R,5R)-3,4-syn-6-(Benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)hex-1-en-3-ol | 156568-08-0

• 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,4R,5R)-3,4-syn-6-(Benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)hex-1-en-3-ol
• 英文别名: (3S,4R,5R)-5-[tert-butyl(dimethyl)silyl]oxy-4-(methoxymethoxy)-6-phenylmethoxyhex-1-en-3-ol
• CAS: 156568-08-0
• 化学式: C₂₁H₃₆O₅Si
• 分子量: 396.599
• InChiKey: LUXNTECOKQMVEM-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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,4R,5R)-3,4-syn-6-(Benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)hex-1-en-3-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.0h， 以85%的产率得到(3S,4R,5R)-6-(Benzyloxy)-4-(methoxymethoxy)hex-1-ene-3,5-diol
  参考文献：
  名称：

  Studies Directed toward the Synthesis of (+)-Sesbanimide A: Construction of the AB-Ring System (A Formal Total Synthesis)

  摘要：

  Complete details of a study leading to the asymmetric synthesis of the AB-ring system of (+)-sesbanimide A (1), a potent cytotoxic agent belonging to the class of sesbania alkaloids, are described. Key features of the synthesis include (a) the stereoselective introduction of the C8 and C9 hydroxyl groups through the use of a diastereoselective catalytic osmylation of enantiomerically enriched alpha-alkoxy allylsilanes and (b) a chelation-controlled nucleophilic addition of a vinyl Grignard reagent to a syn alpha-alkoxy beta-(silyloxy) aldehyde for the introduction of the C7 stereocenter required for assembly of the B-ring.

  DOI：

  10.1021/jo00090a025
• 作为产物：
  描述：

  (E)-4-benzyloxy-2-butenal 在 palladium on activated charcoal 、 四氧化锇 咪唑 、 4-二甲氨基吡啶 、 草酰氯 、 十二/十四烷基二甲基氧化胺 、 氢气 、 四丁基碘化铵 、 lithium 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， -100.0~25.0 ℃ 、101.33 kPa 条件下， 反应 130.0h， 生成 (3S,4R,5R)-3,4-syn-6-(Benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)hex-1-en-3-ol
  参考文献：
  名称：

  Studies Directed toward the Synthesis of (+)-Sesbanimide A: Construction of the AB-Ring System (A Formal Total Synthesis)

  摘要：

  Complete details of a study leading to the asymmetric synthesis of the AB-ring system of (+)-sesbanimide A (1), a potent cytotoxic agent belonging to the class of sesbania alkaloids, are described. Key features of the synthesis include (a) the stereoselective introduction of the C8 and C9 hydroxyl groups through the use of a diastereoselective catalytic osmylation of enantiomerically enriched alpha-alkoxy allylsilanes and (b) a chelation-controlled nucleophilic addition of a vinyl Grignard reagent to a syn alpha-alkoxy beta-(silyloxy) aldehyde for the introduction of the C7 stereocenter required for assembly of the B-ring.

  DOI：

  10.1021/jo00090a025

文献信息

• Studies Directed toward the Synthesis of (+)-Sesbanimide A: Construction of the AB-Ring System (A Formal Total Synthesis)
  作者：Pier F. Cirillo、James S. Panek

  DOI：10.1021/jo00090a025

  日期：1994.6

  Complete details of a study leading to the asymmetric synthesis of the AB-ring system of (+)-sesbanimide A (1), a potent cytotoxic agent belonging to the class of sesbania alkaloids, are described. Key features of the synthesis include (a) the stereoselective introduction of the C8 and C9 hydroxyl groups through the use of a diastereoselective catalytic osmylation of enantiomerically enriched alpha-alkoxy allylsilanes and (b) a chelation-controlled nucleophilic addition of a vinyl Grignard reagent to a syn alpha-alkoxy beta-(silyloxy) aldehyde for the introduction of the C7 stereocenter required for assembly of the B-ring.