benzyl N-[(1R,2R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-1-[(4R,5R)-5-[(1S)-1-hydroxy-3-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(methoxymethoxy)oxan-2-yl]propyl]-2,2-dimethyl-1,3-dioxolan-4-yl]propan-2-yl]carbamate | 198562-89-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl N-[(1R,2R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-1-[(4R,5R)-5-[(1S)-1-hydroxy-3-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(methoxymethoxy)oxan-2-yl]propyl]-2,2-dimethyl-1,3-dioxolan-4-yl]propan-2-yl]carbamate
• CAS: 198562-89-9
• 化学式: C₄₃H₇₉NO₁₅Si₂
• 分子量: 906.269
• InChiKey: KSBALUXQJMPHEU-RFEQNWAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  61
• 可旋转键数：
  27
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  169
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  benzyl N-[(1R,2R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-1-[(4R,5R)-5-[(1S)-1-hydroxy-3-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(methoxymethoxy)oxan-2-yl]propyl]-2,2-dimethyl-1,3-dioxolan-4-yl]propan-2-yl]carbamate 在 palladium on activated charcoal 咪唑 、 氢气 、 碘 、 三苯基膦 作用下， 以 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 生成 (3aR,4R,6R,7R,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-[2-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-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
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 ((1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-2-{(4R,5R)-5-[(S)-1-hydroxy-3-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-hydroxymethyl-ethyl)-carbamic acid benzyl ester 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl N-[(1R,2R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-1-[(4R,5R)-5-[(1S)-1-hydroxy-3-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(methoxymethoxy)oxan-2-yl]propyl]-2,2-dimethyl-1,3-dioxolan-4-yl]propan-2-yl]carbamate
  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.