benzyl 4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)but-2-enoate | 856668-37-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl 4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)but-2-enoate
• CAS: 856668-37-6
• 化学式: C₃₀H₃₉NO₁₃
• 分子量: 621.639
• InChiKey: AYMCGCDMUWSFDN-IONQDRQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  179.06
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  benzyl 4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)but-2-enoate 在 [(COD)Rh((S,S)-Et-DuPHOD)]OTF 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、3.45 MPa 条件下， 反应 48.0h， 生成 benzyl (2S)-4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)butanoate 、 benzyl (2R)-4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)butanoate
  参考文献：
  名称：

  C-Linked Galactosyl Serine AFGP Analogues as Potent Recrystallization Inhibitors

  摘要：

  A series of C-linked antifreeze glycoprotein analogues have been prepared to evaluate antifreeze activity as a function of distance between the carbohydrate moiety and polypeptide backbone. The building blocks for these analogues were prepared using either an olefin cross-metathesis or catalytic asymmetric hydrogenation. Analysis of antifreeze protein-specific activity revealed that only analogue 2a (n = 1) was a potent recrystallization inhibitor and thus has potential medical and industrial applications.

  DOI：

  10.1021/ol050677x
• 作为产物：
  描述：

  allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 在 臭氧 、 四甲基胍 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 benzyl 4-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(tert-butyloxycarbonylamino)but-2-enoate
  参考文献：
  名称：

  C-Linked Galactosyl Serine AFGP Analogues as Potent Recrystallization Inhibitors

  摘要：

  A series of C-linked antifreeze glycoprotein analogues have been prepared to evaluate antifreeze activity as a function of distance between the carbohydrate moiety and polypeptide backbone. The building blocks for these analogues were prepared using either an olefin cross-metathesis or catalytic asymmetric hydrogenation. Analysis of antifreeze protein-specific activity revealed that only analogue 2a (n = 1) was a potent recrystallization inhibitor and thus has potential medical and industrial applications.

  DOI：

  10.1021/ol050677x