Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-but-3-enyl-tetrahydro-pyran-4-yl ester | 856668-31-0

• 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: Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-but-3-enyl-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4R,5S,6R)-3,4,5-triacetyloxy-6-but-3-enyloxan-2-yl]methyl acetate
• CAS: 856668-31-0
• 化学式: C₁₈H₂₆O₉
• 分子量: 386.399
• InChiKey: BRNLBQJFECXYQU-DFBDCSAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-but-3-enyl-tetrahydro-pyran-4-yl ester 、 (S)-benzyl 2-(benzyloxycarbonyl)but-3-enoate 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100%的产率得到benzyl (2S)-6-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2-(benzyloxycarbonylamino)hex-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
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 硼烷 、 potassium tert-butylate 、 氢溴酸 、 六正丁基二锡 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 15.5h， 生成 Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-but-3-enyl-tetrahydro-pyran-4-yl ester
  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