1',2,3,3',4,4',6-hepta-O-acetyl-6'-azido-6'-deoxy-sucrose | 56720-33-3

• 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: 1',2,3,3',4,4',6-hepta-O-acetyl-6'-azido-6'-deoxy-sucrose
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2S,3S,4R,5R)-3,4-diacetyloxy-2-(acetyloxymethyl)-5-(azidomethyl)oxolan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 56720-33-3
• 化学式: C₂₆H₃₅N₃O₁₇
• 分子量: 661.574
• InChiKey: ZUQIAPLWDRHFPY-PNQDPTNESA-N

物化性质

• 熔点：
  143-145 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  46
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  226
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  1',2,3,3',4,4',6-hepta-O-acetyl-6'-azido-6'-deoxy-sucrose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 6'-Azido-6'-deoxysucrose
  参考文献：
  名称：

  Sucrose chemistry. A synthetically useful monoarenesulfonation

  摘要：

  DOI：

  10.1021/jo00180a005
• 作为产物：
  描述：

  1',2,3,3',4,4',6-O-acetyl-6'-O-methanesulfonylsucrose 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以925 mg的产率得到1',2,3,3',4,4',6-hepta-O-acetyl-6'-azido-6'-deoxy-sucrose
  参考文献：
  名称：

  Efficient microwave assisted synthesis of novel 1,2,3-triazole–sucrose derivatives by cycloaddition reaction of sucrose azides and terminal alkynes

  摘要：

  Novel 1-(1',2,3,3',4,4',6-hepta-O-acetyl-6'-deoxy-sucros-6'-yl)-4-substituted-1,2,3-triazoles were synthesized by microwave assisted copper catalyzed 1,3-dipolar cycloaddition of sucrose derived azides with terminal alkynes in excellent yields and in short reaction times. The compound 1',2,3,3',4,4',6-hepta-O-acetyl-6'-azido-6'-deoxy-sucrose was regioselectively synthesized from sucrose by improved procedure and used for the cycloadditions. By combining carbohydrate and 1,2,3-triazole structural motifs, a library of 1,2,3-triazole-sucrose conjugates have been obtained. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.06.017

文献信息

• Synthesis of d-fructose conjugated ligands via C6 and C1 and their corresponding [Ru(bpy)2(L)]Cl2 complexes
  作者：Michael Pröhl、Pascal D. Moser、Justyna A. Czaplewska、Patrick Hoffmann、Tanja Buś、Anja Traeger、Helmar Goerls、Ulrich S. Schubert、Michael Gottschaldt

  DOI：10.1016/j.carres.2017.04.020

  日期：2017.6

  formula [Ru(bpy)2(L)]Cl2 was formed. Acidic cleavage of the d-glucose unit led to the first d-fructose conjugated metal complex viad-fructose C6 in literature. Additionally, pyta-modified d-fructose via C1 and the corresponding Ru complex were synthesized. All compounds were analyzed by Rf values, specific rotation, NMR, IR, UV/Vis and fluorescence spectroscopy, mass spectrometry and elemental analysis

  吡啶基三唑（pyta）修饰的蔗糖配体是通过七步合成法制备的，其中使用d-葡萄糖作为d-果糖的保护基，并从市售蔗糖开始。与Ru（bpy）2 Cl 2前体络合后，形成通式[Ru（bpy）2（L）] Cl 2的蔗糖缀合的Ru络合物。d-葡萄糖单元的酸性裂解导致文献中的第一个d-果糖共轭金属络合物viad-果糖C6。此外，还合成了经由C1的pyta修饰的d-果糖和相应的Ru配合物。通过Rf值，比旋光度，NMR，IR，UV / Vis和荧光光谱，质谱和元素分析来分析所有化合物。
• New synthetic approach to per-O-acetyl-isocyanates, isothiocyanates and thioureas in the disaccharide and cyclodextrin series
  作者：Stephane Menuel、Stanislaw Porwanski、Alain Marsura

  DOI：10.1039/b600023a

  日期：——

  An efficient method for the preparation of per-O-acetyl disaccharides and cyclodextrin isocyanates or isothiocyanates by the phosphine imide strategy is reported. Successful one-pot, high yield syntheses of cellobiose, lactose and sucrose isocyanates or/and isothiocyanates pure β-anomers have been completed starting from their corresponding monoazido-per-O-acetyl derivatives. Transformation of the ACEtris-6-azido-per-O-methylated and the ACEtris-6-azido-per-O-acetylated-α-cyclodextrins or of the 6A-azido-6A-deoxy-per-O-acetyl-β-cyclodextrin into the corresponding isocyanates and/or isothiocyanates is also presented. Finally the conversion of the cyclodextrin isothiocyanates by nucleophilic addition of primary and secondary amines into a large panel of original thioureido-cyclodextrins derivatives is described.

  报告了一种通过膦酰亚胺策略制备过 O-乙酰基二糖和环糊精异氰酸酯或异硫氰酸盐的高效方法。从相应的单叠氮过-O-乙酰基衍生物开始，成功地完成了纤维生物糖、乳糖和蔗糖异氰酸酯或/和异硫氰酸盐纯 β-异构体的单锅高产合成。此外，还介绍了 ACEtris-6-azido-per-O-methylated 和 ACEtris-6-azido-per-O-acetylated-α-cyclodextrin 或 6A-azido-6A-deoxy-per-O-acetyl-β-cyclodextrin 转化为相应的异氰酸酯和/或异硫氰酸盐的情况。最后还介绍了通过伯胺和仲胺的亲核加成将环糊精异硫氰酸酯转化为大量硫代环糊精原始衍生物的过程。
• Amide-linked N-methacryloyl sucrose containing polymers
  作者：Krasimira T. Petrova、Taterao M. Potewar、Osvaldo S. Ascenso、M. Teresa Barros

  DOI：10.1016/j.carbpol.2014.03.050

  日期：2014.9

  1',2,3,3',4,4',6-Hepta-O-benzyl-6'-N-methacryloyl-6'-deoxysucrose 1, 6'-deoxy-6'-N-methacryloyloxyethylureido sucrose 2 and 6,6'-dideoxy-6,6'-N-dimethacryloyloxyethylureido sucrose 3 have been homo-polymerized and copolymerized with styrene by a free radical process, yielding polymer materials with pendant sucrose moieties, attached to the polymer backbone via amide linkages. The results demonstrated that varying the structural features of the monomers, greatly affected the thermal and rheological properties of the polymers. The polymer materials obtained have been characterized by NMR, MALDI-TOF, DSC, AFM and EWC (equilibrium water content). The efficient synthesis of the three novel, regioisomerically pure, N-methacryloylamide sucrose-containing monomers (1, 2 and 3) have been described. (C) 2014 Elsevier Ltd. All rights reserved.
• Sharma, N. K.; Norula, J. L.; Mattey, S. K., Journal of the Indian Chemical Society, 1982, vol. 59, # 3, p. 385 - 388
  作者：Sharma, N. K.、Norula, J. L.、Mattey, S. K.

  DOI：——

  日期：——