(5S,8S,9R)-2-((2S,4S,5S)-(Z)-5-(but-1-enyl)-2-methyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-(hydroxyphenylmethyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione | 562858-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (5S,8S,9R)-2-((2S,4S,5S)-(Z)-5-(but-1-enyl)-2-methyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-(hydroxyphenylmethyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
• 英文别名: (5S,8R,9R)-2-[(2S,4S,5S)-5-[(Z)-but-1-enyl]-2-methyl-1,3-dioxolan-4-yl]-8-hydroxy-8-[hydroxy(phenyl)methyl]-3-methyl-9-tri(propan-2-yl)silyloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
• CAS: 562858-36-0
• 化学式: C₃₂H₄₇NO₈Si
• 分子量: 601.813
• InChiKey: ZSLVFUWVBXBYJG-OFHNCMHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5S,8S,9R)-2-((2S,4S,5S)-(Z)-5-(but-1-enyl)-2-methyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-(hydroxyphenylmethyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione 在 氟化铵 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (5S,8S,9R)-8-benzoyl-2-((2S,4S,5S)-(Z)-5-(but-1-enyl)-2-methyl-[1,3]dioxolan-4-yl)-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
  参考文献：
  名称：

  Asymmetric Total Synthesis of Pseurotin A

  摘要：

  [GRAPHICS]The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a gamma-lactam, an aldol reaction of a benzylidene-substituted ketone, and the late-stage introduction of the benzoyl group by a selective oxidation of a benzylidene moiety with dimethyidioxirane (DMD).

  DOI：

  10.1021/ol034630s
• 作为产物：
  描述：

  (5S,9S)-(Z)-8-benzylidene-2-((2S,4S,5S)-(Z)-5-(but-1-enyl)-2-methyl-[1,3]dioxolan-4-yl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-aza-spiro[4.4]non-2-ene-4,6-dione 在 4 A molecular sieve 、 二甲基二环氧乙烷 作用下， 以 甲醇 为溶剂， 反应 10.5h， 以62%的产率得到(5S,8S,9R)-2-((2S,4S,5S)-(Z)-5-(but-1-enyl)-2-methyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-(hydroxyphenylmethyl)-3-methyl-9-triisopropylsiloxy-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
  参考文献：
  名称：

  Asymmetric Total Synthesis of Pseurotin A

  摘要：

  [GRAPHICS]The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a gamma-lactam, an aldol reaction of a benzylidene-substituted ketone, and the late-stage introduction of the benzoyl group by a selective oxidation of a benzylidene moiety with dimethyidioxirane (DMD).

  DOI：

  10.1021/ol034630s

文献信息

• Asymmetric Total Synthesis of Pseurotin A
  作者：Yujiro Hayashi、Mitsuru Shoji、Shinpei Yamaguchi、Takasuke Mukaiyama、Junichiro Yamaguchi、Hideaki Kakeya、Hiroyuki Osada

  DOI：10.1021/ol034630s

  日期：2003.6.1

  [GRAPHICS]The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a gamma-lactam, an aldol reaction of a benzylidene-substituted ketone, and the late-stage introduction of the benzoyl group by a selective oxidation of a benzylidene moiety with dimethyidioxirane (DMD).