4-(β-D-glucopyranosyl)but-1-ene | 222420-67-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(β-D-glucopyranosyl)but-1-ene
• 英文别名: 3-butenyl β-D-C-glucopyranoside；(2S,3R,4R,5S,6R)-2-but-3-enyl-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 222420-67-9
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: FORUMNNUEYKKDB-SQXHDICFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(β-D-glucopyranosyl)but-1-ene 在 phosphate buffer 、 Aspergillus oryzae β-galactosidase 、 Humicola insolens 、 maleate buffer 作用下， 以 水 为溶剂， 反应 2.0h， 生成 3-4)-O-β-D-glucopyranosyl>but-1-ene
  参考文献：
  名称：

  The role of hydrolases in a synthesis of some epoxyalkyl β-C-cellobiosides

  摘要：

  An endoglucanase from Humicola insolens has been used to glycosylate a range of alkenyl beta-D-C-glucopyranosides with beta-lactosyl fluoride. The resulting trisaccharides have been subjected to the action of a commercial beta-galactosidase to form alkenyl beta-C-cellobiosides. Oxidation of these has given a range of epoxyalkyl beta-C-cellobiosides, putative inhibitors of cellobiohydrolases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01177-6
• 作为产物：
  描述：

  4-(tetra-O-acetyl-β-D-glucopyranosyl)but-1-ene 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以97%的产率得到4-(β-D-glucopyranosyl)but-1-ene
  参考文献：
  名称：

  The role of hydrolases in a synthesis of some epoxyalkyl β-C-cellobiosides

  摘要：

  An endoglucanase from Humicola insolens has been used to glycosylate a range of alkenyl beta-D-C-glucopyranosides with beta-lactosyl fluoride. The resulting trisaccharides have been subjected to the action of a commercial beta-galactosidase to form alkenyl beta-C-cellobiosides. Oxidation of these has given a range of epoxyalkyl beta-C-cellobiosides, putative inhibitors of cellobiohydrolases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01177-6

文献信息

• A 'Glycosynthase'-assisted Synthesis of Some Epoxyalkyl β-C-Oligosaccharides
  作者：Jon K. Fairweather、Robert V. Stick、Stephen G. Withers

  DOI：10.1071/ch00125

  日期：——

  A series of alkenyl β-D-C-glucopyranosides has been glycosylated with α-D-glucopyranosyl fluoride in a ‘Glycosynthase’ reaction to yield a range of alkenyl β-C-cellobiosides and -triosides and in one case a -C-cellotetraoside. Conversion of some of the alkenyl β -D-C-oligosaccharide products into their corresponding epoxides and subsequent deprotection under standard conditions have afforded a panel of epoxyalkyl β -C-oligosaccharides for evaluation as inhibitors of retaining β-glycan hydrolases.

  一系列烯基β-D-C-吡喃葡萄糖苷 在 "糖合成酶 "反应中与α-D-吡喃葡萄糖基氟化物进行糖基化。 糖合成酶 "反应，生成一系列烯基 β-Cellobiosides和-triosides，其中一种是-C-cellotetraoside。将一些烯基 β -D-C-寡糖产物转化为相应的 环氧化物，然后在标准条件下进行脱保护处理，得到了一系列环氧烷基 环氧烷基 β -C -寡糖小组 作为保留 β-聚糖水解酶的抑制剂进行评估。
• The role of hydrolases in a synthesis of some epoxyalkyl β-C-cellobiosides
  作者：Jon K. Fairweather、Robert V. Stick、D.Matthew G. Tilbrook、Hugues Driguez

  DOI：10.1016/s0040-4020(98)01177-6

  日期：1999.3

  An endoglucanase from Humicola insolens has been used to glycosylate a range of alkenyl beta-D-C-glucopyranosides with beta-lactosyl fluoride. The resulting trisaccharides have been subjected to the action of a commercial beta-galactosidase to form alkenyl beta-C-cellobiosides. Oxidation of these has given a range of epoxyalkyl beta-C-cellobiosides, putative inhibitors of cellobiohydrolases. (C) 1999 Elsevier Science Ltd. All rights reserved.