but-1-yn-3-yl (2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside | 194088-20-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: but-1-yn-3-yl (2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside
• CAS: 194088-20-5
• 化学式: C₁₈H₂₄O₁₀
• 分子量: 400.383
• InChiKey: OVIFTCHSADMWLX-BYJDPIGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.11
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  but-1-yn-3-yl (2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside 在 potassium cyanide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到3-butyn-2-yl β-D-glucopyranoside
  参考文献：
  名称：

  A simple synthesis of four stereoisomers of roseoside and their inhibitory activity on leukotriene release from mice bone marrow-derived cultured mast cells

  摘要：

  Four stereoisomers of roseoside (vomifoliol glucosides) were synthesized using glucose as a chiral resolving reagent. The four synthetic stereoisomers exhibited inhibitory activity on leukotriene release from mouse bone marrow-derived cultured mast cells (BMCMC). The (6S)-isomers of roseoside were about twice as active as (6R)-isomers. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.002
• 作为产物：
  描述：

  3-丁炔-2-醇 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 silver trifluoromethanesulfonate 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 以80%的产率得到but-1-yn-3-yl (2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside
  参考文献：
  名称：

  A simple synthesis of four stereoisomers of roseoside and their inhibitory activity on leukotriene release from mice bone marrow-derived cultured mast cells

  摘要：

  Four stereoisomers of roseoside (vomifoliol glucosides) were synthesized using glucose as a chiral resolving reagent. The four synthetic stereoisomers exhibited inhibitory activity on leukotriene release from mouse bone marrow-derived cultured mast cells (BMCMC). The (6S)-isomers of roseoside were about twice as active as (6R)-isomers. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.002