propargyl 2,3,4,6-tetra-O-acetyl-D-galactopyranoside | 83540-91-4

• 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: propargyl 2,3,4,6-tetra-O-acetyl-D-galactopyranoside
• CAS: 83540-91-4
• 化学式: C₁₇H₂₂O₁₀
• 分子量: 386.356
• InChiKey: HKGFUJKLPCRVFW-MFVZMDDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.28
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  propargyl 2,3,4,6-tetra-O-acetyl-D-galactopyranoside 在 氯化亚砜 、 sodium azide 、 sodium ascorbate 、 copper(l) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 二甲基亚砜 为溶剂， 反应 66.0h， 生成 1-[4-(2,3,4-tri-O-acetyl-D-arabinopyranosyloxymethyl)-1H-1,2,3-triazol-1-yl]-[4-(2,3,4,6-tetra-O-acetyl-D-galactopyranosyloxymethyl)-2H-1,2,3-triazol-1-yl]propane
  参考文献：
  名称：

  双-三氮唑缀合的假二糖衍生物及其制备方法

  摘要：

  本发明公开了一种如通式(I)所示的双‑三氮唑缀合的假二糖衍生物，其中：P为羟基或氨基的保护基团/未保护基团，或者P为氢原子，当P为保护基团时，保护方式可以是完全保护或部分保护；R为B片段中连接两个三氮唑基的次甲基上的侧链基团，并且，该次甲基键接于一个三氮唑的2‑位N和另一个三氮唑的1‑位N上；A、C片段为五元或六元单醛糖的糖苷，异头碳的构型为α‑型或β‑型或α/β‑混合构型；A、C片段的糖苷类型相同或相异；n为2，3或4。该衍生物含有三氮唑的母核结构，具有抗菌、抗病毒作用。

  公开号：

  CN104045673B
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 sodium acetate 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 propargyl 2,3,4,6-tetra-O-acetyl-D-galactopyranoside
  参考文献：
  名称：

  Optical control over bioactive ligands at supramolecular surfaces

  摘要：

  处理蛋白质和细菌固定化及它们在β-环糊精超分子平台上的光控制。

  DOI：

  10.1039/c4cc03184a

文献信息

• Synthesis of aryl cluster glycosides by cyclotrimerization of 2-propynyl carbohydrate derivatives
  作者：Robert J. Kaufman、Ravinder S. Sidhu

  DOI：10.1021/jo00146a023

  日期：1982.12
• Sulfuric acid immobilized on silica: an excellent catalyst for Fischer type glycosylation
  作者：Bimalendu Roy、Balaram Mukhopadhyay

  DOI：10.1016/j.tetlet.2007.03.165

  日期：2007.5

  Fischer glycosylation, a widely used technique for the preparation of simple alkyl or aryl glycosides, has a few drawbacks including the use of strong mineral acids, excess alcohols, high temperature and long reaction times. This manuscript highlights a modification using sulfuric acid immobilized on silica as catalyst for the preparation of glycosides from free sugars such as D-glucose, D-galactose, D-mannose, L-rhamnose, L-fucose, N-acetyl-D-glucosamine and D-maltose with a diverse range of alcohols to afford a series of useful sugar derivatives in good to excellent yields. (C) 2007 Elsevier Ltd. All rights reserved.
• A convenient method for constructing novel tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]-pyrimidinones-carbohydrate and amino acid conjugates via copper(I)-catalyzed alkyne-azide ‘Click Chemistry’
  作者：Mohamed A. Ameen、Sebastian Karsten、Jürgen Liebscher

  DOI：10.1016/j.tet.2010.01.071

  日期：2010.3

  Novel conjugates of tetrahydropyridothienopyrimidones and carbohydrates of amino acids linked by 1,2,3-triazoles were synthesized After establishing the tetrahydropyridothienopyrimidones ring system by ring closure, propargyl groups were introduced by N-alkylation Cu-catalyzed cycloaddition of the propargyl products with azido group containing hexoses or amino acids gives the corresponding 1,2,3-triazoles in high yields This methodology also allowed attaching two carbohydrate molecules to the tetrahydropyridothienopyrimidone core Interesting dependence of the regioselectivity of the N-propargylation of the pyrimidone ring oil the exocyclic substituent found adjacent to the pyrimidine-N-atom was observed A remarkable case of a non-catalyzed intramolecular [3+2]-cycloaddition of an alkyne with ail azide to a 1,2,3-triazole was observed. which occurred in the solid state at it or below (C) 2010 Elsevier Ltd All rights reserved