(2S,3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran | 881895-14-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran
• CAS: 881895-14-3
• 化学式: C₂₇H₂₈N₆O₃S
• 分子量: 516.624
• InChiKey: TXMYGXPVSKLGIV-SEFGFODJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  125.21
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 丙酮 为溶剂， 生成 (3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ol
  参考文献：
  名称：

  New One-Carbon Degradative Transformation of β-Alkyl-β-azido Alcohols

  摘要：

  A new transformation of 2-azido-l-hydroxy-containing compounds to nitriles with one carbon less than the starting materials by oxidation was reported. The reaction can be performed under mild conditions.

  DOI：

  10.1021/ol0601996
• 作为产物：
  描述：

  在 甲醇 、 sodium azide 、 碘 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 (2S,3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran
  参考文献：
  名称：

  New One-Carbon Degradative Transformation of β-Alkyl-β-azido Alcohols

  摘要：

  A new transformation of 2-azido-l-hydroxy-containing compounds to nitriles with one carbon less than the starting materials by oxidation was reported. The reaction can be performed under mild conditions.

  DOI：

  10.1021/ol0601996

文献信息

• Regioselective Benzylation of Azido-Containing Monosaccharides
  作者：Xin-Shan Ye、Qiu-Hua Fan、Qin Li、Li-He Zhang

  DOI：10.1055/s-2006-939681

  日期：——

  A regioselective benzylation or p-methoxybenzylation of diols in azido-containing monosaccharide derivatives was reported, and the reaction was performed under the conventional reaction conditions (NaH/BnBr in DMF). The hydroxyl functionality adjacent to the azido group was benzylated selectively in good yields.

  报道了含叠氮基单糖衍生物中二醇的区域选择性苯甲基化或对甲氧基苯甲基化，并且该反应在常规反应条件（NaH/BnBr在DMF中）下进行。与叠氮基相邻的羟基官能团以良好的产率选择性地被苄基化。
• Selective Reduction of Azido Groups in Monosaccharides with Triphenyl-phosphine
  作者：Xin-Shan Ye、Qin Li、Qiu-Hua Fan、Li-He Zhang

  DOI：10.1055/s-2006-950430

  日期：2006.9

  The regioselective reduction of one azido group in glycopyranoside and mannitol derivatives containing two azido functions with triphenylphosphine is described. In cyclic substrates with two secondary azides, equatorial azides were reduced in good yields in preference to axial azides. Steric, but not electronic, factors ­appear to determine the regiochemical outcome of the Staudinger reduction.

  介绍了用三苯基膦还原含有两个叠氮功能的吡喃糖苷和甘露醇衍生物中的一个叠氮基团的区域选择性。在含有两个仲叠氮基团的环状底物中，赤道叠氮基团比轴向叠氮基团更容易被还原。立体因素而非电子因素似乎决定了施陶丁格还原反应的区域化学结果。