3-benzoylamino-8-methyl-2-oxo-2H-1-benzopyran-7-yl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 312911-59-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-benzoylamino-8-methyl-2-oxo-2H-1-benzopyran-7-yl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(3-benzamido-8-methyl-2-oxochromen-7-yl)oxyoxan-2-yl]methyl acetate
• CAS: 312911-59-4
• 化学式: C₃₁H₃₁NO₁₃
• 分子量: 625.586
• InChiKey: BAJCBNDQCMKNHA-KULBADPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3-benzoylamino-8-methyl-2-oxo-2H-1-benzopyran-7-yl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以77%的产率得到3-benzoylamino-8-methyl-2-oxo-2H-1-benzopyran-7-yl α-D-mannopyranoside
  参考文献：
  名称：

  Novobiocin-related compounds: synthesis of 3-benzoylamino-2-oxo-2H-1-benzopyran-7-yl d-glycopyranosides by the trichloroacetimidate methodology

  摘要：

  A general stereoselective method for the synthesis of 4-deoxynovobiocin-related glycosides is described. 3-Benzoylamino-2H-1-benzopyran-7-yl 2,3,4,6-tetra-O-acetyl-D-glycopyranosides of glucose, galactose and mannose were synthesised from appropriate O-glycosyltrichloroacetimidates and N-(7-hydroxy-2-oxo-2H-1-benzopyran-3-yl)benzamides in boiling methylene chloride in the presence of boron trifluoride etherate. Heating of these products in a mixture of triethylamine and methanol gave the corresponding deprotected 3-benzoylamino-2-oxo-2H-1-benzopyran-7-yl beta-D-glycopyranosides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00142-7
• 作为产物：
  描述：

  2,6-二羟基甲苯 在 三氯化铝 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-benzoylamino-8-methyl-2-oxo-2H-1-benzopyran-7-yl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  Novobiocin-related compounds: synthesis of 3-benzoylamino-2-oxo-2H-1-benzopyran-7-yl d-glycopyranosides by the trichloroacetimidate methodology

  摘要：

  A general stereoselective method for the synthesis of 4-deoxynovobiocin-related glycosides is described. 3-Benzoylamino-2H-1-benzopyran-7-yl 2,3,4,6-tetra-O-acetyl-D-glycopyranosides of glucose, galactose and mannose were synthesised from appropriate O-glycosyltrichloroacetimidates and N-(7-hydroxy-2-oxo-2H-1-benzopyran-3-yl)benzamides in boiling methylene chloride in the presence of boron trifluoride etherate. Heating of these products in a mixture of triethylamine and methanol gave the corresponding deprotected 3-benzoylamino-2-oxo-2H-1-benzopyran-7-yl beta-D-glycopyranosides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00142-7