(Z)-1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-2-phenylethylene | 164528-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-2-phenylethylene
• 英文别名: [(2R,3R,4R,5S,6R)-6-[(Z)-2-phenylethenyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 164528-33-0
• 化学式: C₃₇H₃₈O₆
• 分子量: 578.705
• InChiKey: KUCFKZZSXBAWMY-FUNUCCLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-2-phenylethylene 在 甲醇 、 sodium methylate 作用下， 以90%的产率得到(Z)-1-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-2-phenylethylene
  参考文献：
  名称：

  Synthesis and reactions of an (α-d-glucopyranosyl)phenylacetylene

  摘要：

  Silver tetrafluoroborate promoted addition of (phenylethynyl)tributylstannane to 6-O-acety-1,2,3,4-tri-O-benzyl-alpha-D-glucopyranosyl chloride stereoselectively gave a crystalline (alpha-D-glucopyranosyl)phenylacetylene (4) in 73% yield. Compound 4 was epimerized to the beta isomer through its hexacarbonyldicobalt complex, and was also converted into a C-alpha-glycosyl aldehyde (8) by sequential zinc reduction and ozonolysis. The sensitive aldehyde 8 was conveniently isolated and manipulated through its 1,3-diphenylimidazolidine derivative.

  DOI：

  10.1016/0008-6215(94)00326-b
• 作为产物：
  描述：

  1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-2-phenylacetylene 在 溶剂黄146 、 锌 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以84%的产率得到(Z)-1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-2-phenylethylene
  参考文献：
  名称：

  Synthesis and reactions of an (α-d-glucopyranosyl)phenylacetylene

  摘要：

  Silver tetrafluoroborate promoted addition of (phenylethynyl)tributylstannane to 6-O-acety-1,2,3,4-tri-O-benzyl-alpha-D-glucopyranosyl chloride stereoselectively gave a crystalline (alpha-D-glucopyranosyl)phenylacetylene (4) in 73% yield. Compound 4 was epimerized to the beta isomer through its hexacarbonyldicobalt complex, and was also converted into a C-alpha-glycosyl aldehyde (8) by sequential zinc reduction and ozonolysis. The sensitive aldehyde 8 was conveniently isolated and manipulated through its 1,3-diphenylimidazolidine derivative.

  DOI：

  10.1016/0008-6215(94)00326-b