but-2-ynyl β-D-galactopyranoside | 1190202-85-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: but-2-ynyl β-D-galactopyranoside
• 英文别名: but-2-yn-1-yl β-D-galactopyranoside；(2R,3R,4S,5R,6R)-2-but-2-ynoxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1190202-85-7
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: HNYHUFYAOSCYQS-SOYHJAILSA-N

物化性质

• 熔点：
  154 °C
• 沸点：
  469.1±45.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  but-2-ynyl β-D-galactopyranoside 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到but-2-ynyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Glycosylation Using Unprotected Alkynyl Donors

  摘要：

  Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in acetonitrile with 5% AuCl(3) for reaction with various primary alcohol acceptors, the latter used in 10-fold molar excess relative to donor. Donors containing the 2-butynyl group were more reactive, giving good yields of glycoside products at lower temperatures Secondary alcohols could also be used but with diminished efficiency. The propargylic family of donors is especially convenient because they can be easily prepared on large scale by Fischer glycosylation and stored indefinitely before chemoselective activation by the catalyst.

  DOI：

  10.1021/jo901857x
• 作为产物：
  描述：

  but-2-ynyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以90%的产率得到but-2-ynyl β-D-galactopyranoside
  参考文献：
  名称：

  Glycosylation Using Unprotected Alkynyl Donors

  摘要：

  Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in acetonitrile with 5% AuCl(3) for reaction with various primary alcohol acceptors, the latter used in 10-fold molar excess relative to donor. Donors containing the 2-butynyl group were more reactive, giving good yields of glycoside products at lower temperatures Secondary alcohols could also be used but with diminished efficiency. The propargylic family of donors is especially convenient because they can be easily prepared on large scale by Fischer glycosylation and stored indefinitely before chemoselective activation by the catalyst.

  DOI：

  10.1021/jo901857x

文献信息

• Expanding the application scope of glycosidases using click chemistry
  作者：Wen-Ya Lu、Xing-Wen Sun、Chen Zhu、Jian-He Xu、Guo-Qiang Lin

  DOI：10.1016/j.tet.2009.11.044

  日期：2010.1

  Glycosidase-mediated glycosylation of alkynyl alcohols and azide-containing alcohols was followed by a click reaction, affording various types of triazole glycosides. The activities of triazole glycosides detected in Subsequent bioassays show that this procedure is a feasible approach to the development of anti-fungal drugs. (C) 2009 Elsevier Ltd. All rights reserved.
• Glycosylation Using Unprotected Alkynyl Donors
  作者：Sreeman K. Mamidyala、M.G. Finn

  DOI：10.1021/jo901857x

  日期：2009.11.6

  Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in acetonitrile with 5% AuCl(3) for reaction with various primary alcohol acceptors, the latter used in 10-fold molar excess relative to donor. Donors containing the 2-butynyl group were more reactive, giving good yields of glycoside products at lower temperatures Secondary alcohols could also be used but with diminished efficiency. The propargylic family of donors is especially convenient because they can be easily prepared on large scale by Fischer glycosylation and stored indefinitely before chemoselective activation by the catalyst.