(E)-(3S,6R)-6-{(4S,6R)-6-[(E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-non-1-enyl]-2,2,5,5-tetramethyl-[1,3]dioxan-4-yl}-4-methyl-3-triethylsilanyloxy-hept-4-enoic acid phenyl ester | 220484-33-3

• 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: (E)-(3S,6R)-6-{(4S,6R)-6-[(E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-non-1-enyl]-2,2,5,5-tetramethyl-[1,3]dioxan-4-yl}-4-methyl-3-triethylsilanyloxy-hept-4-enoic acid phenyl ester
• CAS: 220484-33-3
• 化学式: C₄₄H₇₈O₆Si₂
• 分子量: 759.271
• InChiKey: ZPSYPMZDELMLEO-YJXQZKGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.81
• 重原子数：
  52.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-(3S,6R)-6-{(4S,6R)-6-[(E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-non-1-enyl]-2,2,5,5-tetramethyl-[1,3]dioxan-4-yl}-4-methyl-3-triethylsilanyloxy-hept-4-enoic acid phenyl ester 在 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 (4R)-4-iPr-3-[(p-tolyl)sulfonyl]-1,3,2-oxazaborolidin-5-one 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 methyl (8E,14E,5R,7S,10R,11S,13R,17R)-17-(tert-butyldimethylsiloxy)-5,11,13-trihydroxy-11,13-O-isopropylidene-8,10,12,12,14-pentamethyl-3-oxo-7-(triethylsiloxy)docosa-8,14-dienoate
  参考文献：
  名称：

  A Study Directed to the Asymmetric Synthesis of the Antineoplastic Macrolide Acutiphycin under Enantioselective Acyclic Stereoselection Based on Chiral Oxazaborolidinone-Promoted Asymmetic Aldol Reactions

  摘要：

  A shortening of the reaction path can be realized by using a series of the chiral oxazaborolidinone-promoted aldol reaction with respect to the practical synthesis of the (+)-acutiphycin seco acid derivative 5. The linear strategy is based on the utilization of five aldol reactions with a sequence of silyl nucleophiles, 7, 8, 35, 10, and 11, in the presence of stoichiometric amounts of the promoter, 1 or 2. The construction of the relative configuration between the stereogenic centers is diastereoselectively controlled by the stereochemistry of the promoter used in the enantioselective aldol reaction, which is nearly independent of that of the substrate (promoter control).

  DOI：

  10.1021/jo990342r
• 作为产物：
  描述：

  (2E,8E,4R,5S,7R,11R)-11-(tert-butyldimethylsiloxy)-5,7-dihydroxy-5,7-O-isopropylidene-2,4,6,6,8-pentamethylhexadeca-2,8-dienal 在 2,6-二甲基吡啶 、 chiral oxazaborolidinone 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (E)-(3S,6R)-6-{(4S,6R)-6-[(E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-non-1-enyl]-2,2,5,5-tetramethyl-[1,3]dioxan-4-yl}-4-methyl-3-triethylsilanyloxy-hept-4-enoic acid phenyl ester
  参考文献：
  名称：

  Toward a practical synthesis of acutiphycin. Highly stereoselective synthesis of C10-epi seco acid derivative via reaction paths shortened by using a series of chiral oxazaborolidinone-promoted aldol reactions

  摘要：

  DOI：

  10.1016/s0040-4039(98)02553-2