benzyl (2R,3R,4R,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(chloromethylsulfonyloxy)-4,5-bis(phenylmethoxy)piperidine-1-carboxylate | 203253-85-4

• 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: benzyl (2R,3R,4R,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(chloromethylsulfonyloxy)-4,5-bis(phenylmethoxy)piperidine-1-carboxylate
• CAS: 203253-85-4
• 化学式: C₄₅H₅₀ClNO₈SSi
• 分子量: 828.498
• InChiKey: HUIDLMOPFWUXSP-NZYKERBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.67
• 重原子数：
  57
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl (2R,3R,4R,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(chloromethylsulfonyloxy)-4,5-bis(phenylmethoxy)piperidine-1-carboxylate 在 六甲基磷酰三胺 、 四丁基氟化铵 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 56.0h， 生成 2,3-di-O-benzyl-N,6-O-carbonyl-1,5-dideoxy-1,5-imino-D-galactitol
  参考文献：
  名称：

  Chemical Transformation of a 1-Deoxynojirimycin Derivative into 1-Deoxymannojirimycin and 1-Deoxygalactostatin

  摘要：

  Treatment of 2,3-di-O-benzyl-N-benzyloxycarbonyl-6-O-t-butyldiphenylsilyl-1-5-dideoxy-1,5-imino-D-glucitol (4) with sodium hydride resulted in an intramolecular cyclization concomitant with silyl migration, giving the carbamate derivative 5 in good yield. This was efficiently converted into 1-deoxymannojirimycin (2) via regioselective p-toluenesulfonylation followed by an inversion reaction at the C-2 position. On the other hand, the monochloromethylsulfonate 10 obtained from 4 underwent configurational change at the C-4 position by the action of sodium benzoate. The resulting benzoate 11 was deprotected to afford 1-deoxygalactostatin (3).

  DOI：

  10.1080/07328309808005772
• 作为产物：
  描述：

  氯甲磺酰氯 、 N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以120 mg的产率得到benzyl (2R,3R,4R,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(chloromethylsulfonyloxy)-4,5-bis(phenylmethoxy)piperidine-1-carboxylate
  参考文献：
  名称：

  Chemical Transformation of a 1-Deoxynojirimycin Derivative into 1-Deoxymannojirimycin and 1-Deoxygalactostatin

  摘要：

  Treatment of 2,3-di-O-benzyl-N-benzyloxycarbonyl-6-O-t-butyldiphenylsilyl-1-5-dideoxy-1,5-imino-D-glucitol (4) with sodium hydride resulted in an intramolecular cyclization concomitant with silyl migration, giving the carbamate derivative 5 in good yield. This was efficiently converted into 1-deoxymannojirimycin (2) via regioselective p-toluenesulfonylation followed by an inversion reaction at the C-2 position. On the other hand, the monochloromethylsulfonate 10 obtained from 4 underwent configurational change at the C-4 position by the action of sodium benzoate. The resulting benzoate 11 was deprotected to afford 1-deoxygalactostatin (3).

  DOI：

  10.1080/07328309808005772

文献信息

• Chemical Transformation of a 1-Deoxynojirimycin Derivative into 1-Deoxymannojirimycin and 1-Deoxygalactostatin
  作者：Shunya Takahashi、Hiroyoshi Kuzuhara

  DOI：10.1080/07328309808005772

  日期：1998.1

  Treatment of 2,3-di-O-benzyl-N-benzyloxycarbonyl-6-O-t-butyldiphenylsilyl-1-5-dideoxy-1,5-imino-D-glucitol (4) with sodium hydride resulted in an intramolecular cyclization concomitant with silyl migration, giving the carbamate derivative 5 in good yield. This was efficiently converted into 1-deoxymannojirimycin (2) via regioselective p-toluenesulfonylation followed by an inversion reaction at the C-2 position. On the other hand, the monochloromethylsulfonate 10 obtained from 4 underwent configurational change at the C-4 position by the action of sodium benzoate. The resulting benzoate 11 was deprotected to afford 1-deoxygalactostatin (3).