Acetic acid (2R,3S,4R,5R,6S)-3-acetylamino-6-benzyloxy-5-benzyloxycarbonylamino-2-methyl-tetrahydro-pyran-4-yl ester | 174151-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6S)-3-acetylamino-6-benzyloxy-5-benzyloxycarbonylamino-2-methyl-tetrahydro-pyran-4-yl ester
• CAS: 174151-39-4
• 化学式: C₂₅H₃₀N₂O₇
• 分子量: 470.522
• InChiKey: UMZLLIMVFLBJQA-AXHBDUOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  112.19
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Acetic acid (2R,3S,4R,5R,6S)-3-acetylamino-6-benzyloxy-5-benzyloxycarbonylamino-2-methyl-tetrahydro-pyran-4-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以100%的产率得到2,4-diacetamido-3-O-acetyl-2,4,6-trideoxy-β-D-gulopyranose
  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-2,3,4,6-tetradeoxy-α-D-erythro-hex-3-enopyranoside 在 sodium tetrahydroborate 、 sodium azide 、 sodium acetate 、 氯化铵 、 间氯过氧苯甲酸 、 nickel dichloride 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 34.92h， 生成 Acetic acid (2R,3S,4R,5R,6S)-3-acetylamino-6-benzyloxy-5-benzyloxycarbonylamino-2-methyl-tetrahydro-pyran-4-yl 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