heptakis(2,3-di-O-methyl)-6I-O-p-tolylsulfonyl-cyclomaltoheptaose | 166305-90-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: heptakis(2,3-di-O-methyl)-6I-O-p-tolylsulfonyl-cyclomaltoheptaose
• 英文别名: heptakis(2,3-di-O-methyl)-6^I-O-p-tolylsulfonyl-cyclomaltoheptaose；Heptakis(2,3-di-O-methyl)-6-O-(p-toluenesulfonyl)-β-cyclodextrin
• CAS: 166305-90-4
• 化学式: C₆₃H₁₀₄O₃₇S
• 分子量: 1485.56
• InChiKey: WPRZXZKHZSHCMZ-MWDJDSKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.35
• 重原子数：
  101.0
• 可旋转键数：
  24.0
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  423.19
• 氢给体数：
  6.0
• 氢受体数：
  37.0

反应信息

• 作为反应物：
  描述：

  heptakis(2,3-di-O-methyl)-6I-O-p-tolylsulfonyl-cyclomaltoheptaose 、 三氟甲烷磺酸甲酯 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以93%的产率得到[(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36S,37R,38S,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecamethoxy-5,15,20,25,30,35-hexakis(methoxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-10-yl]methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  New permethyl-substituted .beta.-cyclodextrin polysiloxanes for use as chiral stationary phases in open tubular column chromatography

  摘要：

  Heptakis(2,3-di-O-methyl)-6-O-tosyl-beta-cyclodextrin (2) was prepared from heptakis(2,3-di-O-methyl)-beta-cyclodextrin (1) in a 31 % yield. The tosyl group of 2 was substituted by p-(allyloxy)phenyl in a yield of 74 % to produce 6-O-(p-(allyloxy)phenyl)heptakis(2,3-di-O-methyl)-beta-cyclodextrin (3). This material was derivatized at the other 6-positions to produce persubstituted 6A-O-(p-(allyloxy)phenyl)-beta-cyclodextrins 4, 5, and 8. Permethylated 6-O-tosyl-beta-cyclodextrin 9, which was used for the preparation of 10-12, was obtained from 2 almost quantitatively. 6-O-(tert-Butyldimethylsilyl)-(heptakis(2,3-di-O-methyl)-beta-cyclodextrin (13) was also obtained from 1 in a 33% yield. Permethylated 6A-deoxy-6A-methylene-beta-cyclodextrin (17) was prepared from 13 by a 4-step process. Seven new permethyl-substituted beta-cyclodextrins bound to polymethylsiloxane were prepared by a hydrosilylation reaction of the permethyl-substituted monoalkenyl-beta-cyclodextrins with polyhydromethylsiloxane. The polymeric phases provide excellent enantiomeric separation of a variety of chiral solutes in open tubular column supercritical fluid chromatography (SFC) and gas chromatography (GC).

  DOI：

  10.1021/jo00070a019
• 作为产物：
  描述：

  heptakis(2,3-di-O-methyl)cyclomaltoheptaose 、 对甲苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 以21%的产率得到heptakis(2,3-di-O-methyl)-6I-O-p-tolylsulfonyl-cyclomaltoheptaose
  参考文献：
  名称：

  6I-氨基-6I-脱氧-2I-VII，3I-VII-十四烷基-O-甲基-环麦芽七糖的合成

  摘要：

  据报道制备了6（I）-氨基-6（I）-脱氧-2（I-VII），3（I-VII）-十四烷基-O-甲基-环麦芽庚糖。已经研究了两种均从β-环糊精（betaCD）开始的不同途径（A和B）。途径A涉及：（i）由betaCD合成庚基（6-O-叔丁基二甲基甲硅烷基）-betaCD；（ii）用甲基碘和氢化钠对仲羟基进行全甲基化；（iii）伯羟基与氟化铵的甲硅烷基化；（iv）每个（2,3-O-甲基）-βCD的O-6位的单甲苯基化; （5）用叠氮化物阴离子亲核取代甲苯磺酰基；（v）在甲醇/水中，在Pd / C存在下，通过水合肼催化转移氢化来还原叠氮基。路线B从已知的6（I）-单叠氮基-6（I）-单脱氧-β-CD（距离β-CD两步）开始，并且需要进行以下操作：（i）使用叔丁基二甲基甲硅烷基氯（TBDMSC1）保护剩余的伯羟基；（ii）用甲基碘和氢化钠对仲羟基进行彻底的甲基化；（iii）用氟化铵除去TBDMS保

  DOI：

  10.1016/j.carres.2004.03.007