2,5-anhydro-6-azido-6-deoxy-D-glucitol | 88777-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-6-azido-6-deoxy-D-glucitol
• 英文别名: (2R,3S,4S,5S)-2-(azidomethyl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 88777-03-1
• 化学式: C₆H₁₁N₃O₄
• 分子量: 189.171
• InChiKey: SXQJFSPBUVMKMT-JGWLITMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.3
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-6-azido-6-deoxy-D-glucitol 、 苄胺 在 高碘酸 、 sodium cyanoborohydride 、 溶剂黄146 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.5h， 以53%的产率得到2,6-anhydro-4-aza-7-azido-4-benzyl-3,4,5,7-tetradeoxy-D-glycero-D-ribo-heptitol
  参考文献：
  名称：

  Synthesis and Application of Carbohydrate-Derived Morpholine Amino Acids

  摘要：

  The synthesis of series of diversely functionalized epsilon-morpholine amino acids (MAAs, 5a-h) starting from an E-sugar amino acid and following a two-step oxidative glycol cleavage/reductive amination strategy, is described. In an alternative synthetic scheme, diastereoisomerically pure delta-MAAs (12a,b) were obtained. Oligopeptides containing MAAs were prepared either by direct incorporation of a MAA building block or by subjecting a fully assembled SAA-containing peptide to the two-step glycol cleavage/reductive amination procedure.

  DOI：

  10.1021/jo048630x
• 作为产物：
  描述：

  2,5-anhydro-6-azido-6-deoxy-1,3-O-isopropylidene-D-glucitol 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到2,5-anhydro-6-azido-6-deoxy-D-glucitol
  参考文献：
  名称：

  Synthesis and Application of Carbohydrate-Derived Morpholine Amino Acids

  摘要：

  The synthesis of series of diversely functionalized epsilon-morpholine amino acids (MAAs, 5a-h) starting from an E-sugar amino acid and following a two-step oxidative glycol cleavage/reductive amination strategy, is described. In an alternative synthetic scheme, diastereoisomerically pure delta-MAAs (12a,b) were obtained. Oligopeptides containing MAAs were prepared either by direct incorporation of a MAA building block or by subjecting a fully assembled SAA-containing peptide to the two-step glycol cleavage/reductive amination procedure.

  DOI：

  10.1021/jo048630x

文献信息

• Synthesis of 6-amino-2,5-anhydro-6-deoxy- and -1,6-dideoxy-d-glucitol and some derivatives thereof
  作者：János Kuszmann、Péter Dvortsák

  DOI：10.1016/0008-6215(83)88478-x

  日期：1983.11

  expected 6-deoxy derivative, the (acyclic) 5-enoalditol. The synthesis of 44 was conducted via 2,5-anhydro-1,6-di-O-tosyl- d -mannitol (36), which was obtained from 1,6-di-O-benzoyl-3,4-O-isopropylidene- d -mannitol in satisfactory yield. Ditosylate 36 was converted into a 2,5:3,6-dianhydro monotosylate which, on reduction with lithium aluminum hydride, gave the 1-deoxy derivative. Opening of the 3

  摘要以d-甘露醇为原料，合成了6-氨基-2,5-脱水-6-脱氧-和-1,6-二脱氧-d-葡萄糖醇（44）及其衍生物。将3，4-二-O-烯丙基-1，2：5，6-二脱水-d-甘露糖醇转化为2，5-脱水-6-溴化合物8，其溴原子被叠氮化物代替。通过在乙醇-乙酸-水中用PdC处理除去烯丙基，并用硫化氢-吡啶还原叠氮基。通过使用甲醛-甲酸将形成的氨基甲基化，得到1-N-6-O-亚甲基化合物为主要产物，其对硼氢化物的还原具有抗性。用乙酸中的活化锌处理8，而不是预期的6-脱氧衍生物，得到（无环）5-烯醛醇。44的合成是通过2,5-脱水-1,6-二-O-甲苯磺酰基-d-甘露醇（36）进行的，由1，6-二-O-苯甲酰基-3，4-O-异亚丙基-d-甘露糖醇以令人满意的产率获得。将二甲苯磺酸酯36转化为2,5：3,6-二脱水单甲苯磺酸酯，将其用氢化铝锂还原后得到1-脱氧衍生物。用氢溴酸打开3,6-脱水环导致生