N-benzyl-α-D-ribopyranosylamine | 70399-59-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-α-D-ribopyranosylamine
• 英文别名: N-Benzyl-D-arabinosylamin；(3S,4S,5R)-2-(benzylamino)tetrahydro-2H-pyran-3,4,5-triol；N-benzyl-β-D-ribopyranosylamine；(2R,3R,4S,5R)-2-(benzylamino)tetrahydro-2H-pyran-3,4,5-triol；2-(benzylamino)oxane-3,4,5-triol
• CAS: 70399-59-6；70399-60-9；70399-61-0；74036-10-5；85280-63-3；85280-64-4；108942-11-6；108942-12-7
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: GQYUAOVGPQRZHJ-YIBTVLSRSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  436.3±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.78
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.95
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-benzyl-α-D-ribopyranosylamine 、 3-溴丙烯 在 indium 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.17h， 以72%的产率得到(5R,6S,7R)-4-benzylamino-5,6,7,8-tetrahydroxyoct-1-ene
  参考文献：
  名称：

  Highly Selective Indium Mediated Allylation of Unprotected Pentosylamines

  摘要：

  A straightforward functionalization of D-pentoses is reported, which affords homoallylaminopolyols in two steps and uses ion exchange chromatography as the only purification operation. The key indium-mediated allylation is effected on unprotected glycosylamines and occurs with good to excellent syn stereoselection. Validation of the synthetic utility of the method was exemplified by a 3-step synthesis of an optically active 1,2,3,6-tetrahydropyridine from D-xylose.

  DOI：

  10.1021/ol3002656
• 作为产物：
  描述：

  阿拉伯糖 、 苄胺 以 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到N-benzyl-α-D-ribopyranosylamine
  参考文献：
  名称：

  Highly Selective Indium Mediated Allylation of Unprotected Pentosylamines

  摘要：

  A straightforward functionalization of D-pentoses is reported, which affords homoallylaminopolyols in two steps and uses ion exchange chromatography as the only purification operation. The key indium-mediated allylation is effected on unprotected glycosylamines and occurs with good to excellent syn stereoselection. Validation of the synthetic utility of the method was exemplified by a 3-step synthesis of an optically active 1,2,3,6-tetrahydropyridine from D-xylose.

  DOI：

  10.1021/ol3002656