tert-butyl (-)-(3S,5S,10R,11R)-1-tert-butyldimethylsilyloxy-3,5:10,11-di(isopropylidenedioxy)-7-oxo-tridec-8-en-13-oate | 244217-28-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (-)-(3S,5S,10R,11R)-1-tert-butyldimethylsilyloxy-3,5:10,11-di(isopropylidenedioxy)-7-oxo-tridec-8-en-13-oate
• 英文别名: tert-butyl 2-[(4R,5R)-5-[(E)-4-[(4S,6S)-6-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-2,2-dimethyl-1,3-dioxan-4-yl]-3-oxobut-1-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]acetate
• CAS: 244217-28-5
• 化学式: C₂₉H₅₂O₈Si
• 分子量: 556.813
• InChiKey: JEPWAYRFVNVRMB-WDZWUIKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (-)-(3S,5S,10R,11R)-1-tert-butyldimethylsilyloxy-3,5:10,11-di(isopropylidenedioxy)-7-oxo-tridec-8-en-13-oate 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 3.5h， 生成 tert-butyl (+)-(3S,5R,7R,10R,11R)-1-tert-butyldimethylsilyloxy-7-hydroxy-3,5:10,11-di(isopropylidenedioxy)-tridecan-13-oate
  参考文献：
  名称：

  First Stereocontrolled Synthesis of the (3S,5R,7R,10R,11R)-C1−C13 Fragment of Nystatin A₁

  摘要：

  A convergent stereoselective synthesis of the (3S,5R,7R,10R,11R)-C1-C13 fragment of Nystatin Al is reported in this paper. This fragment contains an all-syn-1,3,5-triol subunit and a syn-1,2-diol moiety. The main features of the synthesis are the enzymatic desymmetrization of a meso diol to obtain an enantiomerically pure syn-4,6-dihydroxy-2-keto-phosphonate, chiral sulfoxide chemistry to prepare an alpha-(R)-hydroxyaldehyde and 2-trimethylsilyl thiazole reagent to synthesize a synthesize a syn-alpha,beta-(R,S)-dihydroxy aldehyde.

  DOI：

  10.1021/jo990245y
• 作为产物：
  描述：

  (3S,5R)-7-acetoxy-1-hydroxy-3,5-isopropylidenedioxy-heptane 在 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 ruthenium trichloride 、 sodium periodate 、 正丁基锂 、 sodium 、 sodium hydride 作用下， 以 四氢呋喃 、 四氯化碳 、 乙二醇二甲醚 、 phosphate buffer 、 乙醚 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 36.58h， 生成 tert-butyl (-)-(3S,5S,10R,11R)-1-tert-butyldimethylsilyloxy-3,5:10,11-di(isopropylidenedioxy)-7-oxo-tridec-8-en-13-oate
  参考文献：
  名称：

  First Stereocontrolled Synthesis of the (3S,5R,7R,10R,11R)-C1−C13 Fragment of Nystatin A₁

  摘要：

  A convergent stereoselective synthesis of the (3S,5R,7R,10R,11R)-C1-C13 fragment of Nystatin Al is reported in this paper. This fragment contains an all-syn-1,3,5-triol subunit and a syn-1,2-diol moiety. The main features of the synthesis are the enzymatic desymmetrization of a meso diol to obtain an enantiomerically pure syn-4,6-dihydroxy-2-keto-phosphonate, chiral sulfoxide chemistry to prepare an alpha-(R)-hydroxyaldehyde and 2-trimethylsilyl thiazole reagent to synthesize a synthesize a syn-alpha,beta-(R,S)-dihydroxy aldehyde.

  DOI：

  10.1021/jo990245y

文献信息

• First Stereocontrolled Synthesis of the (3<i>S</i>,5<i>R</i>,7<i>R</i>,10<i>R</i>,11<i>R</i>)-C1−C13 Fragment of Nystatin A₁
  作者：Guy Solladié、Nicole Wilb、Claude Bauder、Carlo Bonini、Licia Viggiani、Lucia Chiummiento

  DOI：10.1021/jo990245y

  日期：1999.7.1

  A convergent stereoselective synthesis of the (3S,5R,7R,10R,11R)-C1-C13 fragment of Nystatin Al is reported in this paper. This fragment contains an all-syn-1,3,5-triol subunit and a syn-1,2-diol moiety. The main features of the synthesis are the enzymatic desymmetrization of a meso diol to obtain an enantiomerically pure syn-4,6-dihydroxy-2-keto-phosphonate, chiral sulfoxide chemistry to prepare an alpha-(R)-hydroxyaldehyde and 2-trimethylsilyl thiazole reagent to synthesize a synthesize a syn-alpha,beta-(R,S)-dihydroxy aldehyde.