benzyl (2S)-5-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(benzyloxycarbonylamino)pent-3-enoate | 856668-32-1

• 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 (2S)-5-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(benzyloxycarbonylamino)pent-3-enoate
• CAS: 856668-32-1
• 化学式: C₃₄H₃₉NO₁₃
• 分子量: 669.683
• InChiKey: ZLCWMWWPHNUZDI-YWTJPTAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  48.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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 (2S)-5-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(benzyloxycarbonylamino)pent-3-enoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (S)-2-Amino-5-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-pentanoic acid
  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：

  (S)-benzyl 2-(benzyloxycarbonyl)but-3-enoate 、 allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 在 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以98%的产率得到benzyl (2S)-5-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(benzyloxycarbonylamino)pent-3-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