3,4,6-tri-O-benzyl-1,2-di-O-chloroacetyl-α,β-D-glucopyranose | 250273-79-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-1,2-di-O-chloroacetyl-α,β-D-glucopyranose
• CAS: 250273-79-1
• 化学式: C₃₁H₃₂Cl₂O₈
• 分子量: 603.496
• InChiKey: QYLUZPYFMDQGSG-MVRMALISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  41.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-1,2-di-O-chloroacetyl-α,β-D-glucopyranose 在 氢溴酸 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 3.0h， 以95%的产率得到3,4,6-tri-O-benzyl-2-O-chloroacetyl-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  Total Synthesis of Caloporoside

  摘要：

  The first total synthesis of the fungal metabolite caloporoside 1, a strong and selective inhibitor of phospholipase C, is described. Both sugar units of its complex disaccharidic segment were obtained from 3,4,6-tri-O-benzyl-D-glucopyranose 14 as a common building block, with D-gluco-->D-manno inversions as the key strategic elements. This particular substitution reaction occurred readily on the acyclic segment (27-->28), whereas ultrasonication was required to override adverse stereoelectronic effects upon formation of beta-D-mannopyranoside unit 34. The (16R)-hydroxyheptadecylsalicylic acid part of 1 was efficiently prepared by a palladium-catalyzed Suzuki cross coupling reaction of aryltriflate 7 with the 9-alkyl-9-BBN derivative formed from alkene 6 and 9-H-9-BBN.

  DOI：

  10.1021/jo9800098
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-1,2-O-(S)-(1-ethoxyethylidene)-α-D-glucopyranose 在 吡啶 、 盐酸 、 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 生成 3,4,6-tri-O-benzyl-1,2-di-O-chloroacetyl-α,β-D-glucopyranose
  参考文献：
  名称：

  Total Synthesis of Caloporoside

  摘要：

  The first total synthesis of the fungal metabolite caloporoside 1, a strong and selective inhibitor of phospholipase C, is described. Both sugar units of its complex disaccharidic segment were obtained from 3,4,6-tri-O-benzyl-D-glucopyranose 14 as a common building block, with D-gluco-->D-manno inversions as the key strategic elements. This particular substitution reaction occurred readily on the acyclic segment (27-->28), whereas ultrasonication was required to override adverse stereoelectronic effects upon formation of beta-D-mannopyranoside unit 34. The (16R)-hydroxyheptadecylsalicylic acid part of 1 was efficiently prepared by a palladium-catalyzed Suzuki cross coupling reaction of aryltriflate 7 with the 9-alkyl-9-BBN derivative formed from alkene 6 and 9-H-9-BBN.

  DOI：

  10.1021/jo9800098

文献信息

• Total Synthesis of Vancomycin—Part 4: Attachment of the Sugar Moieties and Completion of the Synthesis
  作者：K. C. Nicolaou、Helen J. Mitchell、Nareshkumar F. Jain、Toshikazu Bando、Robert Hughes、Nicolas Winssinger、Swaminathan Natarajan、Alexandros E. Koumbis

  DOI：10.1002/(sici)1521-3765(19990903)5:9<2648::aid-chem2648>3.0.co;2-q

  日期：1999.9.3