benzyl 4-azido-2-benzyloxycarbonylamino-2,4,6-trideoxy-α-D-gulopyranoside | 174151-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 4-azido-2-benzyloxycarbonylamino-2,4,6-trideoxy-α-D-gulopyranoside
• 英文别名: benzyl N-[(2S,3R,4S,5R,6R)-5-azido-4-hydroxy-6-methyl-2-phenylmethoxyoxan-3-yl]carbamate
• CAS: 174151-37-2
• 化学式: C₂₁H₂₄N₄O₅
• 分子量: 412.445
• InChiKey: KNZJIYCNFJQMSN-JBCQCRMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 4-azido-2-benzyloxycarbonylamino-2,4,6-trideoxy-α-D-gulopyranoside 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 乙醇 为溶剂， 反应 0.75h， 生成 ((2S,3R,4R,5R,6R)-5-Amino-2-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester
  参考文献：
  名称：

  The synthesis of derivatives of 2,4-diamino-2,4,6-trideoxy-d-gulo- and l-altro-hexopyranoses

  摘要：

  Syntheses of two derivatives of two 2,4-diamino-2,4,6-trideoxyhexoses having the D-gulo (16) and L-altro (29) configuration have been described. Derivative 16 was obtained by two routes starting from benzyl 2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside. Derivative 29 was obtained from 3,4-di-O-acetyl-L-rhamnal in a 10-step reaction sequence.

  DOI：

  10.1016/0008-6215(95)00291-x
• 作为产物：
  描述：

  benzyl 2-benzyloxycarbonylamino-6-bromo-2,6-dideoxy-α-D-glucopyranoside 在 sodium azide 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 三正丁基氢锡 、 sodium hydride 、 氯化铵 、 1-(2,4,6-三异丙基苯基磺酰)咪唑 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 28.0h， 生成 benzyl 4-azido-2-benzyloxycarbonylamino-2,4,6-trideoxy-α-D-gulopyranoside
  参考文献：
  名称：

  The synthesis of derivatives of 2,4-diamino-2,4,6-trideoxy-d-gulo- and l-altro-hexopyranoses

  摘要：

  Syntheses of two derivatives of two 2,4-diamino-2,4,6-trideoxyhexoses having the D-gulo (16) and L-altro (29) configuration have been described. Derivative 16 was obtained by two routes starting from benzyl 2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside. Derivative 29 was obtained from 3,4-di-O-acetyl-L-rhamnal in a 10-step reaction sequence.

  DOI：

  10.1016/0008-6215(95)00291-x