n-pentenyl 2,3,4-tri-O-benzyl-6-O-[2-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-α-D-mannopyranoside | 1187620-71-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: n-pentenyl 2,3,4-tri-O-benzyl-6-O-[2-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-α-D-mannopyranoside
• CAS: 1187620-71-8
• 化学式: C₇₉H₇₈O₂₁
• 分子量: 1363.48
• InChiKey: QBOUWONNSDKNOU-XXVWHRPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.41
• 重原子数：
  100.0
• 可旋转键数：
  31.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  255.03
• 氢给体数：
  2.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  n-pentenyl 2,3,4-tri-O-benzyl-6-O-[2-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-α-D-mannopyranoside 、 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl fluoride 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到n-pentenyl 2,3,4-tri-O-benzyl-6-O-[2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)α-D-mannopyranosyl]-α-D-mannopyranoside
  参考文献：
  名称：

  Reaction of 1,2-Orthoesters with HF−Pyridine: A Method for the Preparation of Partly Unprotected Glycosyl Fluorides and Their Use in Saccharide Synthesis

  摘要：

  Glycosyl fluorides can be prepared In an efficient manner by treatment of pyranose- or furanose-derived 1,2-orthoesters, with hydrogen fluoride pyridine (HF-py). The method is compatible with the presence of a variety of protecting groups, including tert-butyldiphenyl silyl ethers, and can be applied to sugar derivatives with free hydroxyl groups, thus avoiding the need for the protection-deprotection steps.

  DOI：

  10.1021/ol901630d
• 作为产物：
  描述：

  2-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl fluoride 、 n-pentenyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以60%的产率得到n-pentenyl 2,3,4-tri-O-benzyl-6-O-[2-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-α-D-mannopyranoside
  参考文献：
  名称：

  Reaction of 1,2-Orthoesters with HF−Pyridine: A Method for the Preparation of Partly Unprotected Glycosyl Fluorides and Their Use in Saccharide Synthesis

  摘要：

  Glycosyl fluorides can be prepared In an efficient manner by treatment of pyranose- or furanose-derived 1,2-orthoesters, with hydrogen fluoride pyridine (HF-py). The method is compatible with the presence of a variety of protecting groups, including tert-butyldiphenyl silyl ethers, and can be applied to sugar derivatives with free hydroxyl groups, thus avoiding the need for the protection-deprotection steps.

  DOI：

  10.1021/ol901630d