tert-butyl (2R,3R,4R,5R)-2-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methylcarbamoyl]-5-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3,4-bis(phenylmethoxy)pyrrolidine-1-carboxylate | 210479-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (2R,3R,4R,5R)-2-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methylcarbamoyl]-5-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3,4-bis(phenylmethoxy)pyrrolidine-1-carboxylate
• CAS: 210479-91-7
• 化学式: C₅₈H₇₁N₃O₁₂
• 分子量: 1002.21
• InChiKey: PRCYDJHGKPHXNL-RDYHJBSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.91
• 重原子数：
  73.0
• 可旋转键数：
  21.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  161.58
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,3R,4R,5R)-2-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methylcarbamoyl]-5-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3,4-bis(phenylmethoxy)pyrrolidine-1-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 42.0h， 生成 (2R,3R,4R,5R)-5-Aminomethyl-3,4-dihydroxy-pyrrolidine-2-carboxylic acid ((2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-amide; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Synthesis of ester-and amide-linked pseudo-azadisaccharides via coupling of d-glucose with 6-amino-6-deoxy-2,5-imino-d-glucitol

  摘要：

  Hydrolytically-resistant pseudodisaccharides incorporating an azafuranose have been prepared by coupling 6-amino-2,5-imino-D-glucitol derivatives with D-glucose, either through an ester or an amide bond. Synthesis of the azasugar templates was achieved by nucleophilic opening of a C-2 symmetric bis-aziridine deriving from D-mannitol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00817-x
• 作为产物：
  描述：

  1-O-acetyl-3,4-di-O-benzyl-6-[(tert-butyloxycarbonyl)amino]-2,5-[(tert-butyloxycarbonyl)imino]-2,5,6-trideoxy-D-glucitol 在 sodium dichromate 、 硫酸 、 sodium methylate 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 反应 19.0h， 生成 tert-butyl (2R,3R,4R,5R)-2-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methylcarbamoyl]-5-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3,4-bis(phenylmethoxy)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of ester-and amide-linked pseudo-azadisaccharides via coupling of d-glucose with 6-amino-6-deoxy-2,5-imino-d-glucitol

  摘要：

  Hydrolytically-resistant pseudodisaccharides incorporating an azafuranose have been prepared by coupling 6-amino-2,5-imino-D-glucitol derivatives with D-glucose, either through an ester or an amide bond. Synthesis of the azasugar templates was achieved by nucleophilic opening of a C-2 symmetric bis-aziridine deriving from D-mannitol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00817-x