N-((2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis(benzyloxy)cyclohexyl)oxy)tetrahydro-2H-pyran-3-yl)naphthalene-2-sulfonamide | 1228173-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-((2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis(benzyloxy)cyclohexyl)oxy)tetrahydro-2H-pyran-3-yl)naphthalene-2-sulfonamide
• CAS: 1228173-27-0
• 化学式: C₅₇H₅₉NO₁₂S
• 分子量: 982.161
• InChiKey: COIICYJZSGBXIE-OHFLSQPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  71.0
• 可旋转键数：
  21.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  171.47
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-((2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis(benzyloxy)cyclohexyl)oxy)tetrahydro-2H-pyran-3-yl)naphthalene-2-sulfonamide 在 disodium hydrogenphosphate 、 sodium amalgam 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以75%的产率得到(2R,3S,4R,5R,6R)-5-amino-2-(hydroxymethyl)-6-(((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis(benzyloxy)cyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diol
  参考文献：
  名称：

  Intramolecular α-Glucosaminidation: Synthesis of Mycothiol

  摘要：

  A protected cyclitol aglycon was tethered to an (N-arylsulfonyl)glucosamine donor by a methylene linker; the exclusively alpha-selective intramolecular glycosyation reaction was then initiated by electrophilic activation of the thioglycoside donor portion. Further transformations of the glycosylation product to give the M. tuberculosis detoxifier mycothiol and its oxidized congener, the disulfide mycothione, are detailed.

  DOI：

  10.1021/ol1008334
• 作为产物：
  描述：

  (2R,3S,4R,5R,6R)-2-(acetoxymethyl)-5-(naphthalene-2-sulfonamido)-6-(((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis(benzyloxy)cyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以99%的产率得到N-((2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis(benzyloxy)cyclohexyl)oxy)tetrahydro-2H-pyran-3-yl)naphthalene-2-sulfonamide
  参考文献：
  名称：

  Intramolecular α-Glucosaminidation: Synthesis of Mycothiol

  摘要：

  A protected cyclitol aglycon was tethered to an (N-arylsulfonyl)glucosamine donor by a methylene linker; the exclusively alpha-selective intramolecular glycosyation reaction was then initiated by electrophilic activation of the thioglycoside donor portion. Further transformations of the glycosylation product to give the M. tuberculosis detoxifier mycothiol and its oxidized congener, the disulfide mycothione, are detailed.

  DOI：

  10.1021/ol1008334