(3aR,4R,6R,7R,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4-phenyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine | 198562-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3aR,4R,6R,7R,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4-phenyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine
• 英文别名: [(3aR,4R,6R,7R,7aR)-7-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-4-phenyl-3a,4,5,6,7,7a-hexahydro-[1,3]dioxolo[4,5-c]pyridin-6-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 198562-96-8
• 化学式: C₂₇H₄₉NO₄Si₂
• 分子量: 507.861
• InChiKey: PGKGZONDECTAQK-RMRNXIRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.63
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,4R,6R,7R,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4-phenyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3R,4R,5R,6R)-2-Hydroxymethyl-6-phenyl-piperidine-3,4,5-triol; hydrochloride
  参考文献：
  名称：

  Synthesis of Carbohydrate Mimics: α-1-C-Substituted-deoxymannojirimycins

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(97)10144-7
• 作为产物：
  描述：

  {(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxymethyl-2-[(4R,5R)-5-((S)-hydroxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-carbamic acid benzyl ester 在 palladium on activated charcoal 吡啶 、 咪唑 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3aR,4R,6R,7R,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4-phenyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine
  参考文献：
  名称：

  Synthesis of Carbohydrate Mimics: α-1-C-Substituted-deoxymannojirimycins

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(97)10144-7

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.