Benzoic acid (S)-4-{(4R,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-hydroxy-butyl ester | 198562-83-3

• 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: Benzoic acid (S)-4-{(4R,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-hydroxy-butyl ester
• CAS: 198562-83-3
• 化学式: C₃₃H₄₉NO₉Si
• 分子量: 631.839
• InChiKey: ASDXBSKRTFYJDB-FOECPVOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  44.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  132.78
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (S)-4-{(4R,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-hydroxy-butyl ester 在 palladium on activated charcoal 吡啶 、 咪唑 、 sodium hydroxide 、 potassium tert-butylate 、 氢气 、 碘 、 三苯基膦 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 、 甲苯 为溶剂， 生成 (3aR,4R,5R,9aR,9bR)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-g]indolizine
  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：

  Benzoic acid 3-[(3aR,6R,7R,7aR)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl]-propyl ester 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 Benzoic acid (S)-4-{(4R,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-hydroxy-butyl ester
  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