[(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-carbamic acid benzyl ester | 192804-37-8

• 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: [(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-carbamic acid benzyl ester
• 英文别名: benzyl N-[(3aR,4R,5R,7aR)-4-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-7-phenyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-yl]carbamate
• CAS: 192804-37-8
• 化学式: C₂₉H₃₉NO₅Si
• 分子量: 509.718
• InChiKey: OMRONTFBUQCLNM-VEYUFSJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-carbamic acid benzyl ester 在 palladium on activated charcoal 二甲基硫 、 氢气 、 sodium cyanoborohydride 、 臭氧 作用下， 生成 [(3aR,4S,6R,7R,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-4-phenyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-6-yl]-methanol
  参考文献：
  名称：

  Glycomimetics:  A Versatile de Novo Synthesis of β-1-C-Aryl-deoxymannojirimycin Analogues

  摘要：

  The synthesis of 11 beta-1-C-aryl-deoxymannojirimycin analogues using a versatile de novo strategy is described. The origins of this report are derived from several recent developments in the area of C-1-substituted glycomimetic polyhydroxylated piperidines. This study is designed as a structure-activity comparison to explore the effects of aryl substitution on the ability of the title compounds to inhibit glycosidase enzymes. The polyhydroxylated piperidine ring was constructed using vinyl bromide 10, which was synthesized in six steps from the bromobenzene microbial oxidation metabolite bromo diol 9. A palladium-catalyzed Suzuki cross-coupling of vinyl bromide 10 and the corresponding arylboronic acid served as the key pseudoanomeric carbon-carbon bond-forming step. Ozonolysis and selective reduction of the resultant carbonyl functions followed by reductive amination served to produce the azasugar ring. The complete NMR analysis of the resultant piperidine ring stereochemistry is also discussed. Fully deprotected beta-1-C-aryl-deoxymannojirimycin analogues 8.HCl were obtained upon acidic deprotection.

  DOI：

  10.1021/jo970585o
• 作为产物：
  描述：

  [(3aR,4R,5R,7aS)-7-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-carbamic acid benzyl ester 、 苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以89%的产率得到[(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-phenyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Glycomimetics:  A Versatile de Novo Synthesis of β-1-C-Aryl-deoxymannojirimycin Analogues

  摘要：

  The synthesis of 11 beta-1-C-aryl-deoxymannojirimycin analogues using a versatile de novo strategy is described. The origins of this report are derived from several recent developments in the area of C-1-substituted glycomimetic polyhydroxylated piperidines. This study is designed as a structure-activity comparison to explore the effects of aryl substitution on the ability of the title compounds to inhibit glycosidase enzymes. The polyhydroxylated piperidine ring was constructed using vinyl bromide 10, which was synthesized in six steps from the bromobenzene microbial oxidation metabolite bromo diol 9. A palladium-catalyzed Suzuki cross-coupling of vinyl bromide 10 and the corresponding arylboronic acid served as the key pseudoanomeric carbon-carbon bond-forming step. Ozonolysis and selective reduction of the resultant carbonyl functions followed by reductive amination served to produce the azasugar ring. The complete NMR analysis of the resultant piperidine ring stereochemistry is also discussed. Fully deprotected beta-1-C-aryl-deoxymannojirimycin analogues 8.HCl were obtained upon acidic deprotection.

  DOI：

  10.1021/jo970585o

文献信息

• Synthesis of Carbohydrate Mimics: α-1-C-Substituted-deoxymannojirimycins
  作者：Carl R Johnson、Brian A Johns

  DOI：10.1016/s0040-4039(97)10144-7

  日期：1997.11

  Methodology for the construction of diverse alpha-I-C-substituted-deoxymannojirimycin analogues is reported. The pseudoanomeric carbon-carbon bond was formed using a Suzuki cross-coupling between vinyl bromide 5, derived biocatalytically from bromobenzene, and an aryl, alkyl, or carbohydrate boron coupling partner. Ozonolysis and stereoselective reduction followed by an intramolecular nucleophilic ring closing served to form the polyhydroxylated piperidine ring. (C) 1997 Elsevier Science Ltd.
• Glycomimetics:  A Versatile <i>de Novo</i> Synthesis of β-1-<i>C</i>-Aryl-deoxymannojirimycin Analogues
  作者：Carl R. Johnson、Brian A. Johns

  DOI：10.1021/jo970585o

  日期：1997.8.1

  The synthesis of 11 beta-1-C-aryl-deoxymannojirimycin analogues using a versatile de novo strategy is described. The origins of this report are derived from several recent developments in the area of C-1-substituted glycomimetic polyhydroxylated piperidines. This study is designed as a structure-activity comparison to explore the effects of aryl substitution on the ability of the title compounds to inhibit glycosidase enzymes. The polyhydroxylated piperidine ring was constructed using vinyl bromide 10, which was synthesized in six steps from the bromobenzene microbial oxidation metabolite bromo diol 9. A palladium-catalyzed Suzuki cross-coupling of vinyl bromide 10 and the corresponding arylboronic acid served as the key pseudoanomeric carbon-carbon bond-forming step. Ozonolysis and selective reduction of the resultant carbonyl functions followed by reductive amination served to produce the azasugar ring. The complete NMR analysis of the resultant piperidine ring stereochemistry is also discussed. Fully deprotected beta-1-C-aryl-deoxymannojirimycin analogues 8.HCl were obtained upon acidic deprotection.