6^A,6^C-heptakis(2,3-di-O-methyl)-β-cyclodextrin | 168704-85-6

• 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-heptakis(2,3-di-O-methyl)-β-cyclodextrin
• 英文别名: 6^A,6^C-di-O-heptakis(2,3-di-O-methyl)-β-cyclodextrin；[(1R,2R,3S,4R,6R,8R,9R,11R,13R,14R,16R,18R,19R,21R,23R,24R,26R,27R,28S,29R,30R,46R,49R,50R,52R,54R,55S,61S,62R,63S,64R,65S,66R,67S,68R)-8,13,18,23-tetrakis(hydroxymethyl)-2,3,27,28,54,55,61,62,63,64,65,66,67,68-tetradecamethoxy-33,33,43,43-tetraoxo-5,7,10,12,15,17,20,22,25,32,44,47,48,51,53,60-hexadecaoxa-33lambda6,43lambda6-dithiaundecacyclo[27.18.6.26,9.211,14.216,19.221,24.234,37.239,42.249,52.126,30.04,46]octahexaconta-34,36,39,41,56,58-hexaen-50-yl]methanol；[(1R,2R,3S,4R,6R,8R,9R,11R,13R,14R,16R,18R,19R,21R,23R,24R,26R,27R,28S,29R,30R,46R,49R,50R,52R,54R,55S,61S,62R,63S,64R,65S,66R,67S,68R)-8,13,18,23-tetrakis(hydroxymethyl)-2,3,27,28,54,55,61,62,63,64,65,66,67,68-tetradecamethoxy-33,33,43,43-tetraoxo-5,7,10,12,15,17,20,22,25,32,44,47,48,51,53,60-hexadecaoxa-33λ6,43λ6-dithiaundecacyclo[27.18.6.26,9.211,14.216,19.221,24.234,37.239,42.249,52.126,30.04,46]octahexaconta-34,36,39,41,56,58-hexaen-50-yl]methanol
• CAS: 168704-85-6
• 化学式: C₆₉H₁₀₆O₃₉S₂
• 分子量: 1623.71
• InChiKey: NTQJBJIKPWTGGN-SGJXESGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  110
• 可旋转键数：
  19
• 环数：
  25.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  463
• 氢给体数：
  5
• 氢受体数：
  39

反应信息

• 作为反应物：
  描述：

  6^A,6^C-heptakis(2,3-di-O-methyl)-β-cyclodextrin 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 以81%的产率得到6^A,6^C-diazido-6^A,6^C-dideoxyheptakis(2,3-di-O-methyl)-β-cyclodextrin
  参考文献：
  名称：

  Novel cyclodextrin-oligosiloxane copolymers for use as stationary phases to separate enantiomers in open tubular column supercritical fluid chromatography

  摘要：

  Five novel beta- (or alpha-) cyclodextrin- hexasiloxane copolymers have been prepared by a seven- (or nine-) step process. A key step was the reaction of partially alkylated beta- (or alpha-) cyclodextrin (8, 9, or 10) with p,p'-methylenebis(benzenesulfonyl chloride) to form a bissulfonate ester on the smaller rim of cyclodextrin. These bissulfonates were reacted with sodium p-(allyloxy)phenoxide followed by alkylation to form the peralkylated bis(allyloxyphenyl) beta- (or alpha-) cyclodextrins 17-20. Beta-Cyclodextrin bissulfonate ester 11 was also reacted with sodium azide followed by methylation, reduction, and acylation to form permethylated N,N'-bis[(allyloxy)benzoyl]-6A,6C-diamino-6A,6C-dideoxy-beta-cyclodextrin (24). The bisalkenes were copolymerized with dodecamethylhexasiloxane by the hydrosilylation process to give the cyclodextrin-containing copolymers. The copolymeric phases provided excellent enantiomeric separation of a variety of chiral solutes in open tubular column supercritical fluid chromatography (SFC).

  DOI：

  10.1021/jo00061a035
• 作为产物：
  描述：

  4,4’-亚甲基双(苯磺酰氯) 、 heptakis(2,3-di-O-methyl)cyclomaltoheptaose 在 吡啶 作用下， 反应 3.0h， 以26%的产率得到6^A,6^C-heptakis(2,3-di-O-methyl)-β-cyclodextrin
  参考文献：
  名称：

  Novel cyclodextrin-oligosiloxane copolymers for use as stationary phases to separate enantiomers in open tubular column supercritical fluid chromatography

  摘要：

  Five novel beta- (or alpha-) cyclodextrin- hexasiloxane copolymers have been prepared by a seven- (or nine-) step process. A key step was the reaction of partially alkylated beta- (or alpha-) cyclodextrin (8, 9, or 10) with p,p'-methylenebis(benzenesulfonyl chloride) to form a bissulfonate ester on the smaller rim of cyclodextrin. These bissulfonates were reacted with sodium p-(allyloxy)phenoxide followed by alkylation to form the peralkylated bis(allyloxyphenyl) beta- (or alpha-) cyclodextrins 17-20. Beta-Cyclodextrin bissulfonate ester 11 was also reacted with sodium azide followed by methylation, reduction, and acylation to form permethylated N,N'-bis[(allyloxy)benzoyl]-6A,6C-diamino-6A,6C-dideoxy-beta-cyclodextrin (24). The bisalkenes were copolymerized with dodecamethylhexasiloxane by the hydrosilylation process to give the cyclodextrin-containing copolymers. The copolymeric phases provided excellent enantiomeric separation of a variety of chiral solutes in open tubular column supercritical fluid chromatography (SFC).

  DOI：

  10.1021/jo00061a035

文献信息

• Yi, Guoliang; Bradshaw, Jerald S.; Rossiter, Bryant E., Journal of Heterocyclic Chemistry, 1995, vol. 32, # 2, p. 621 - 626
  作者：Yi, Guoliang、Bradshaw, Jerald S.、Rossiter, Bryant E.、Malik, Abdul、Yun, Hao、Lee, Milton L.

  DOI：——

  日期：——
• Novel cyclodextrin-oligosiloxane copolymers for use as stationary phases to separate enantiomers in open tubular column supercritical fluid chromatography
  作者：Guoliang Yi、Jerald S. Bradshaw、Bryant E. Rossiter、Shawn L. Reese、Patrik Petersson、Karin E. Markides、Milton L. Lee

  DOI：10.1021/jo00061a035

  日期：1993.4

  Five novel beta- (or alpha-) cyclodextrin- hexasiloxane copolymers have been prepared by a seven- (or nine-) step process. A key step was the reaction of partially alkylated beta- (or alpha-) cyclodextrin (8, 9, or 10) with p,p'-methylenebis(benzenesulfonyl chloride) to form a bissulfonate ester on the smaller rim of cyclodextrin. These bissulfonates were reacted with sodium p-(allyloxy)phenoxide followed by alkylation to form the peralkylated bis(allyloxyphenyl) beta- (or alpha-) cyclodextrins 17-20. Beta-Cyclodextrin bissulfonate ester 11 was also reacted with sodium azide followed by methylation, reduction, and acylation to form permethylated N,N'-bis[(allyloxy)benzoyl]-6A,6C-diamino-6A,6C-dideoxy-beta-cyclodextrin (24). The bisalkenes were copolymerized with dodecamethylhexasiloxane by the hydrosilylation process to give the cyclodextrin-containing copolymers. The copolymeric phases provided excellent enantiomeric separation of a variety of chiral solutes in open tubular column supercritical fluid chromatography (SFC).