(2R,4R,5S,6R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-4-[(E)-2-(methoxymethoxy)ethenyl]-2,6-dimethyl-9-phenylmethoxynonane-1,5-diol | 135799-72-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,4R,5S,6R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-4-[(E)-2-(methoxymethoxy)ethenyl]-2,6-dimethyl-9-phenylmethoxynonane-1,5-diol
• CAS: 135799-72-3
• 化学式: C₂₈H₅₀O₆Si
• 分子量: 510.787
• InChiKey: BVGFCGGPVCJNAD-MGXYLUKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  35.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2R,4R,5S,6R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-4-[(E)-2-(methoxymethoxy)ethenyl]-2,6-dimethyl-9-phenylmethoxynonane-1,5-diol 在 对甲苯磺酸 作用下， 以78%的产率得到(2S,3R)-2-<(1R,2R)-4-(Benzyloxy)-2-<(tert-butyldimethylsilyl)oxy>-1-methylbutyl>-3-<(2R)-3-hydroxy-2-methylpropyl>-5-methoxy-1,2,3,4-tetrahydrofuran
  参考文献：
  名称：

  Highly stereoselective SE' additions of .alpha.-alkoxy allylstannanes to chiral aldehydes. Synthesis of a C-1-C-9 subunit of tylonolide

  摘要：

  The racemic alpha-alkoxy allylic stannane RS4 adds to the 2S aldehyde 24 to afford the homoaldol adduct 25 (45%) derived exclusively from the S enantiomer S4 along with isomerized (R)-gamma-alkoxy allylstannane 26 of > 80% ee (50%) and unreacted aldehyde (40%). Use of the nonracemic alpha-alkoxy allylstannane 28 (1:1 mixture of diastereomers) in excess leads to the homoaldol adduct 29, which is transformed in two steps to lactol ether 31, an intermediate in Nicolaou's synthesis of O-micinosyl tylonolide.

  DOI：

  10.1021/jo00019a003
• 作为产物：
  描述：

  (2S,3R)-5-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-2-methylpentanal 在 三氟化硼乙醚 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2R,4R,5S,6R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-4-[(E)-2-(methoxymethoxy)ethenyl]-2,6-dimethyl-9-phenylmethoxynonane-1,5-diol
  参考文献：
  名称：

  Highly stereoselective SE' additions of .alpha.-alkoxy allylstannanes to chiral aldehydes. Synthesis of a C-1-C-9 subunit of tylonolide

  摘要：

  The racemic alpha-alkoxy allylic stannane RS4 adds to the 2S aldehyde 24 to afford the homoaldol adduct 25 (45%) derived exclusively from the S enantiomer S4 along with isomerized (R)-gamma-alkoxy allylstannane 26 of > 80% ee (50%) and unreacted aldehyde (40%). Use of the nonracemic alpha-alkoxy allylstannane 28 (1:1 mixture of diastereomers) in excess leads to the homoaldol adduct 29, which is transformed in two steps to lactol ether 31, an intermediate in Nicolaou's synthesis of O-micinosyl tylonolide.

  DOI：

  10.1021/jo00019a003