(2R,3R,4R,5S)-3,4-Bis-benzyloxy-2-(tert-butoxycarbonylamino-methyl)-5-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | 210479-87-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5S)-3,4-Bis-benzyloxy-2-(tert-butoxycarbonylamino-methyl)-5-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,3R,4R,5R)-2-[[(2S,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxane-2-carbonyl]oxymethyl]-5-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3,4-bis(phenylmethoxy)pyrrolidine-1-carboxylate
• CAS: 210479-87-1
• 化学式: C₅₈H₇₀N₂O₁₃
• 分子量: 1003.2
• InChiKey: PHMOQTWFNXWSSC-OJHITPKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.34
• 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：
  158.78
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-3,4-Bis-benzyloxy-2-(tert-butoxycarbonylamino-methyl)-5-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 40.0h， 以85%的产率得到(2R,3R,4R,5S)-2-(tert-Butoxycarbonylamino-methyl)-3,4-dihydroxy-5-((2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-carbonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  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 4-二甲氨基吡啶 、 sodium methylate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 (2R,3R,4R,5S)-3,4-Bis-benzyloxy-2-(tert-butoxycarbonylamino-methyl)-5-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  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