allyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-D-glucopyranoside | 859857-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-D-glucopyranoside
• 英文别名: allyl 6-azido-2,3,4-tri-O-acetyl-6-deoxy-β-D-glucopyranose；allyl 6-deoxy-6-azido-2,3,4-tri-O-acetyl β-D-glucopyranoside
• CAS: 859857-33-3
• 化学式: C₁₅H₂₁N₃O₈
• 分子量: 371.347
• InChiKey: HTEHODGXMLRXJK-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  146.12
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-D-glucopyranoside 在 ruthenium trichloride 、 sodium periodate 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Cationic Charged Helical Glycopolypeptide Using Ring Opening Polymerization of 6-Deoxy-6-azido-glyco-N-carboxyanhydride

  摘要：

  Glycopolypeptides with a defined secondary structure are of significance in understanding biological phenomena. Synthetic glycopolypeptides, or polypeptides featuring pendant carbohydrate moieties, have been of particular interest in the field of tissue engineering and drug delivery. In this work, we have synthesized charged water-soluble glycopolypeptides that adopt a helical conformation in water. This was carried out by the synthesis of a glyco-N-carboxyanhydride (glyco-NCA) containing an azide group at the sixth position of the carbohydrate ring. Subsequently, the NCA was polymerized to obtain azide-containing glycopolypeptides having good control over molecular weight and polydispersity index (PDI) in high yields. We were also able to control the incorporation of the azide group by synthesizing random co-glycopolypeptide containing 6-deoxy-6-azido and regular 6-OAc functionalized glucose. This azide functionality allows for the easy attachment of a bioactive group, which could potentially enhance the biological activity of the glycopolypeptide. We were able to obtain water-soluble charged glycopolypeptides by both reducing the azide groups into amines and using CuAAC with propargylamine. These charged glycopolypeptides were shown to have a helical conformation in water. Preliminary studies showed that these charged glycopolypeptides showed good biocompatibility and were efficiently taken up by HepG2 cells.

  DOI：

  10.1021/bm5009537
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-allyloxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以666 mg的产率得到allyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  A short route for the synthesis of “sweet” macrocycles via a click-dimerization–ring-closing metathesis approach

  摘要：

  本文介绍了一种简便灵活的方法，利用级联反应：单击二聚化和闭环偏析，制备含有不同碳水化合物分子的大环分子。

  DOI：

  10.1039/b502682b

文献信息

• Synthesis of 1,2,3-Triazole-Linked Glycoconjugates of N-(2-Aminoethyl)glycine: Building Blocks for the Construction of Combinatorial Glycopeptide Libraries
  作者：Thomas Ziegler、Kai Günther

  DOI：10.1055/s-0033-1339137

  日期：——

  blocks for the construction of combinatorial glycopeptide libraries. Twenty-nine glycoconjugate building blocks based on the N-(2-aminoethyl)glycine (AEG) backbone and sugars linked to the backbone by a 1,2,3-triazole moiety were prepared via copper-catalyzed 1,3-dipolar cycloaddition of monosaccharides bearing an azide group and N-4-pentynoyl-AEG. The initial glycoconjugates were converted to the corresponding

  摘要 通过N-（2-氨基乙基）甘氨酸（AEG）骨架和通过1,2,3-三唑部分与骨架连接的糖，形成29个糖缀合物结构单元，通过铜催化的1,3-偶极环加成反应制备。带有叠氮基和N -4-戊炔基-AEG的单糖。将最初的糖缀合物分别转化为相应的酸和五氟苯基酯，它们是构建组合糖肽文库的有用组成部分。 通过N-（2-氨基乙基）甘氨酸（AEG）骨架和通过1,2,3-三唑部分与骨架连接的糖，形成29个糖缀合物结构单元，通过铜催化的1,3-偶极环加成反应制备。带有叠氮基和N -4-戊炔基-AEG的单糖。将最初的糖缀合物分别转化为相应的酸和五氟苯基酯，它们是构建组合糖肽文库的有用组成部分。