6^A,6^C,6^E-tris-azido-6^A,6^C,6^E-trideoxy-6^B,6^D,6^F-tri-O-methyl-hexakis(2,3-di-O-methyl) cyclomaltohexaose | 72665-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6^A,6^C,6^E-tris-azido-6^A,6^C,6^E-trideoxy-6^B,6^D,6^F-tri-O-methyl-hexakis(2,3-di-O-methyl) cyclomaltohexaose
• 英文别名: 6^A,6^C,6^E-triazido-6^A7,^6C,^E-trideoxy-6^B,6^D,6^F-tri-O-methyl-hexakis-(2,3-di-O-methyl)cyclomaltohexaose；(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31S,32R,33S,34R,35S,36R,37S,38R,39S,40R,41S,42R)-5,15,25-tris(azidomethyl)-31,32,33,34,35,36,37,38,39,40,41,42-dodecamethoxy-10,20,30-tris(methoxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29-dodecaoxaheptacyclo[26.2.2.23,6.28,11.213,16.218,21.223,26]dotetracontane
• CAS: 72665-49-7
• 化学式: C₅₁H₈₇N₉O₂₇
• 分子量: 1258.3
• InChiKey: NPPMRLFHGDPSSP-IZLCEEQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  87
• 可旋转键数：
  24
• 环数：
  22.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  292
• 氢给体数：
  0
• 氢受体数：
  33

反应信息

• 作为反应物：
  描述：

  二氧化碳 、 6^A,6^C,6^E-tris-azido-6^A,6^C,6^E-trideoxy-6^B,6^D,6^F-tri-O-methyl-hexakis(2,3-di-O-methyl) cyclomaltohexaose 在 triphenylphosphine resin 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以78%的产率得到6^A,6^C,6^E-tris-isocyanato-6^A,6^C,6^E-trideoxy-6^B,6^D,6^F-tri-O-methyl-hexakis(2,3-di-O-methyl) cyclomaltohexaose
  参考文献：
  名称：

  New synthetic approach to per-O-acetyl-isocyanates, isothiocyanates and thioureas in the disaccharide and cyclodextrin series

  摘要：

  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。

  DOI：

  10.1039/b600023a
• 作为产物：
  描述：

  α-环糊精 、 碘甲烷 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 、 sodium azide 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 以50%的产率得到6^A,6^C,6^E-tris-azido-6^A,6^C,6^E-trideoxy-6^B,6^D,6^F-tri-O-methyl-hexakis(2,3-di-O-methyl) cyclomaltohexaose
  参考文献：
  名称：

  Synthesis of symmetrically modified α-cyclodextrins: an efficient and easy method

  摘要：

  Efficient and simple synthetic methods of designed specific synthons of cyclodextrins are fundamental for the further development of more sophisticated supramolecular devices. Here, a new two step synthesis was proposed for the obtention of the 6(A),6(C),6(E)-triazido-6(A),6(C),6(E)-trideoxy-6(B),6(D),6(F)-tri-O-methylhexakis-(2,3-di-O-methyl)cyclomaltohexaose on a large scale. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01313-3

文献信息

• 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。
• Synthesis of symmetrically modified α-cyclodextrins: an efficient and easy method
  作者：Romain Heck、L. Jicsinszky、Alain Marsura

  DOI：10.1016/s0040-4039(03)01313-3

  日期：2003.7

  Efficient and simple synthetic methods of designed specific synthons of cyclodextrins are fundamental for the further development of more sophisticated supramolecular devices. Here, a new two step synthesis was proposed for the obtention of the 6(A),6(C),6(E)-triazido-6(A),6(C),6(E)-trideoxy-6(B),6(D),6(F)-tri-O-methylhexakis-(2,3-di-O-methyl)cyclomaltohexaose on a large scale. (C) 2003 Elsevier Science Ltd. All rights reserved.