pent-4-enyl 2,3,5,6-tetra-O-acetyl-α,β-D-glucofuranoside | 223483-87-2

• 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: pent-4-enyl 2,3,5,6-tetra-O-acetyl-α,β-D-glucofuranoside
• 英文别名: [(2R)-2-acetyloxy-2-[(2R,3S,4R)-3,4-diacetyloxy-5-pent-4-enoxyoxolan-2-yl]ethyl] acetate
• CAS: 223483-87-2
• 化学式: C₁₉H₂₈O₁₀
• 分子量: 416.425
• InChiKey: XOLYQHQPHOOVCM-DQROZCCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 pent-4-enyl 2,3,5,6-tetra-O-acetyl-α,β-D-glucofuranoside 在 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到methyl 4-O-(2,3,5,6-tetra-O-acetyl-β-D-glucofuranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  含有呋喃糖苷单元的二糖的便捷合成

  摘要：

  摘要通过氯化铁促进4-戊烯-1-醇与d-葡萄糖的一锅反应，合成了Pent-4-enyl 2,3,5,6-tetra-O-acetyl- d-糖呋喃糖苷。 ，分别在异质培养基中添加d-甘露糖和d-半乳糖，然后进行原位乙酰化。这些正戊烯基糖苷是有效的呋喃呋喃糖基供体，因此已用于随后合成与古细菌糖脂和原生动物糖缀合物有关的各种呋喃糖基-吡喃糖苷型或呋喃糖基-呋喃糖苷型二糖。

  DOI：

  10.1016/s0008-6215(96)00268-6
• 作为产物：
  描述：

  4-戊烯-1-醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 三氯化铁 作用下， 以 乙腈 为溶剂， 反应 15.0h， 生成 pent-4-enyl 2,3,5,6-tetra-O-acetyl-α,β-D-glucofuranoside
  参考文献：
  名称：

  含有呋喃糖苷单元的二糖的便捷合成

  摘要：

  摘要通过氯化铁促进4-戊烯-1-醇与d-葡萄糖的一锅反应，合成了Pent-4-enyl 2,3,5,6-tetra-O-acetyl- d-糖呋喃糖苷。 ，分别在异质培养基中添加d-甘露糖和d-半乳糖，然后进行原位乙酰化。这些正戊烯基糖苷是有效的呋喃呋喃糖基供体，因此已用于随后合成与古细菌糖脂和原生动物糖缀合物有关的各种呋喃糖基-吡喃糖苷型或呋喃糖基-呋喃糖苷型二糖。

  DOI：

  10.1016/s0008-6215(96)00268-6

文献信息

• Synthesis and liquid-crystalline properties of novel archaeal diether-type glycolipids possessing one or two furanosyl units
  作者：Rachel Auzély-Velty、Thierry Benvegnu、Grahame Mackenzie、Julie A Haley、John W Goodby、Daniel Plusquellec

  DOI：10.1016/s0008-6215(98)00291-2

  日期：1998.12

  Archaeal diether-type analogues possessing one or two furanosyl polar head groups and methyl branched aliphatic moieties were synthesized by glycosylation of glycerolipids with pent-4-enyl 2,3,5,6-tetra-O-acetyl-D-glycofuranoside as the donors. The products were shown to form thermotropic and lyotropic liquid crystalline mesophases, tubules and vesicles. The self-assembling properties of the compounds prepared were found to be similar to those of naturally occurring materials, in that they exhibited columnar thermotropic mesophases and hexagonal lyotropic phases. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of novel ammonium and selenonium ions and their evaluation as inhibitors of UDP-galactopyranose mutase
  作者：Natacha Veerapen、Yue Yuan、David A.R. Sanders、B. Mario Pinto

  DOI：10.1016/j.carres.2004.07.012

  日期：2004.9

  The syntheses of two ammonium salts of 1,4-dideoxy-1,4-imino-D-galactitol containing erythritol sulfate side chains are described. The parent compound is a known inhibitor of the enzyme UDP-galactopyranose mutase (UDP-galactopyranose furanomutase, E.C. 5.4.99.9), which is responsible for the conversion of UDP-galactopyranose into UDP-galactofuranose and is presumably protonated in its active form. The side chain was chosen because it is present in a known sulfonium ion alpha-glucosidase inhibitor, salacinol. The syntheses of the selenonium analogues derived from 1,4-dideoxy-1,4-seleno-D-galactitol are also described. The synthetic strategy in the syntheses of all four salts involved the nucleophilic attack of a protected derivative of the alditol at the least hindered carbon of 2,4-O-benzylidene D- or L-erythritol-1,3-cyclic sulfate to give adducts that were subsequently deprotected. The importance of different protecting groups used in the various syntheses is also highlighted. Enzyme inhibition assays carried out on these compounds, and the corresponding sulfonium ions synthesized previously, show that they are poor inhibitors of UDP-galactopyranose mutase. (C) 2004 Elsevier Ltd. All rights reserved.