Methanesulfonic acid (S)-{(4S,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-phenyl-methyl ester | 198562-91-3

• 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: Methanesulfonic acid (S)-{(4S,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-phenyl-methyl ester
• CAS: 198562-91-3
• 化学式: C₃₆H₅₉NO₉SSi₂
• 分子量: 738.103
• InChiKey: NCXIJSMQMODTLN-BQCXQQNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.93
• 重原子数：
  49.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  118.62
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (S)-{(4S,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-phenyl-methyl ester 在 palladium on activated charcoal 盐酸 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 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 吡啶 、 咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Methanesulfonic acid (S)-{(4S,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-phenyl-methyl 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