(2S,8S,9R)-1,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2,8-dimethyl-decan-5-one | 743472-08-4

• 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: (2S,8S,9R)-1,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2,8-dimethyl-decan-5-one
• 英文别名: (2S,8S,9R)-1,9-bis[[tert-butyl(dimethyl)silyl]oxy]-10-[(4-methoxyphenyl)methoxy]-2,8-dimethyldecan-5-one
• CAS: 743472-08-4
• 化学式: C₃₂H₆₀O₅Si₂
• 分子量: 580.996
• InChiKey: GSFBXNZEXXOTOC-JCGRVDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.03
• 重原子数：
  39
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,8S,9R)-1,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2,8-dimethyl-decan-5-one 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到(2R,3S,6R,9S)-2-(4-Methoxy-benzyloxymethyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undecane
  参考文献：
  名称：

  Short Synthesis of the 6,6-Spiroketal Cores of Spirofungins A and B

  摘要：

  Initial efforts toward the total synthesis of the antifungal antibiotics spirofungins A and B are reported. A short and efficient synthesis of the C9-C20 6,6-spiroketal fragments of both compounds is described. This asymmetric approach uses a very efficient alkylation of a lithiated N,N-dimethylhydrazone followed by spiroketal formation under acidic conditions.

  DOI：

  10.1021/ol0491078
• 作为产物：
  描述：

  3R-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2R-methyl-butyraldehyde 在 palladium on activated charcoal 正丁基锂 、 三甲基氯硅烷 、 氢气 、 silica gel 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 90.0h， 生成 (2S,8S,9R)-1,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2,8-dimethyl-decan-5-one
  参考文献：
  名称：

  Short Synthesis of the 6,6-Spiroketal Cores of Spirofungins A and B

  摘要：

  Initial efforts toward the total synthesis of the antifungal antibiotics spirofungins A and B are reported. A short and efficient synthesis of the C9-C20 6,6-spiroketal fragments of both compounds is described. This asymmetric approach uses a very efficient alkylation of a lithiated N,N-dimethylhydrazone followed by spiroketal formation under acidic conditions.

  DOI：

  10.1021/ol0491078

文献信息

• Short Synthesis of the 6,6-Spiroketal Cores of Spirofungins A and B
  作者：Luiz C. Dias、Luciana G. de Oliveira

  DOI：10.1021/ol0491078

  日期：2004.7.1

  Initial efforts toward the total synthesis of the antifungal antibiotics spirofungins A and B are reported. A short and efficient synthesis of the C9-C20 6,6-spiroketal fragments of both compounds is described. This asymmetric approach uses a very efficient alkylation of a lithiated N,N-dimethylhydrazone followed by spiroketal formation under acidic conditions.