1,5-anhydro-3-(benzylamino)-3,N,4,O-carbonyl-2,3,6-trideoxy-D-ribo-hexa-1,5-dienopyranose | 160849-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,5-anhydro-3-(benzylamino)-3,N,4,O-carbonyl-2,3,6-trideoxy-D-ribo-hexa-1,5-dienopyranose
• CAS: 160849-60-5
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: RVHJBFJRBWAGOU-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-3-(benzylamino)-3,N,4,O-carbonyl-2,3,6-trideoxy-D-ribo-hexa-1,5-dienopyranose 在 二甲基二环氧乙烷 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 12.83h， 生成
  参考文献：
  名称：

  Staurosporine and ent-Staurosporine:  The First Total Syntheses, Prospects for a Regioselective Approach, and Activity Profiles¹

  摘要：

  The total syntheses of staurosporine and ent-staurosporine have been achieved. Both glycosidic bonds were built from glycal precursors. The first was constructed by intermolecular coupling of an indole anion with a 1,2-anhydrosugar derived from an endo-glycal by direct epoxidation. The second bond was assembled from an exo-glycal by intramolecular iodoglycosylation.

  DOI：

  10.1021/ja952907g
• 作为产物：
  描述：

  1,5-anhydro-2,3-dideoxy-3-(trichloroacetamido)-6-O-(triisopropylsilyl)-D-ribo-hex-1-enopyranose 在 吡啶 、 potassium tert-butylate 、 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 生成 1,5-anhydro-3-(benzylamino)-3,N,4,O-carbonyl-2,3,6-trideoxy-D-ribo-hexa-1,5-dienopyranose
  参考文献：
  名称：

  Staurosporine and ent-Staurosporine:  The First Total Syntheses, Prospects for a Regioselective Approach, and Activity Profiles¹

  摘要：

  The total syntheses of staurosporine and ent-staurosporine have been achieved. Both glycosidic bonds were built from glycal precursors. The first was constructed by intermolecular coupling of an indole anion with a 1,2-anhydrosugar derived from an endo-glycal by direct epoxidation. The second bond was assembled from an exo-glycal by intramolecular iodoglycosylation.

  DOI：

  10.1021/ja952907g

文献信息

• Epoxides derived from pyranosyl dienes: Unusually stable glycosyl donors
  作者：J.T. Link、Samuel J. Danishefsky、Gayle Schulte

  DOI：10.1016/0040-4039(94)88445-5

  日期：1994.12

  appropriately substituted for use in a total synthesis of staurosporine has been synthesized. The mono-epoxides and bis-epoxides obtained from treatment of this diene with dimethyldioxirane are unusually stable.

  已经合成了适当取代用于星形孢菌素的全合成的吡喃糖基二烯。通过用二甲基二环氧乙烷处理该二烯而获得的单环氧化物和双环氧化物异常稳定。