6(A),6(B)-dimesitylenesulfonyl-α-CD | 91899-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6(A),6(B)-dimesitylenesulfonyl-α-CD
• 英文别名: [(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31R,32R,33R,34R,35R,36R,37R,38R,39R,40R,41R,42R)-31,32,33,34,35,36,37,38,39,40,41,42-dodecahydroxy-10,15,20,25-tetrakis(hydroxymethyl)-30-[(2,4,6-trimethylphenyl)sulfonyloxymethyl]-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]dotetracontan-5-yl]methyl 2,4,6-trimethylbenzenesulfonate
• CAS: 91899-91-1
• 化学式: C₅₄H₈₀O₃₄S₂
• 分子量: 1337.34
• InChiKey: VBXFGBUHOMCTSZ-GQSIQSQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.4
• 重原子数：
  90
• 可旋转键数：
  12
• 环数：
  24.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  538
• 氢给体数：
  16
• 氢受体数：
  34

反应信息

• 作为反应物：
  描述：

  6(A),6(B)-dimesitylenesulfonyl-α-CD 在 sodium tetrahydroborate 作用下， 生成
  参考文献：
  名称：

  6A6B-, 6A6C-, and 6A6D-disulfonates of .alpha.-cyclodextrin

  摘要：

  DOI：

  10.1021/ja00331a061
• 作为产物：
  描述：

  2,4,6-三甲基苯磺酰氯 、 α-环糊精 在 吡啶 作用下， 反应 2.0h， 以7.3%的产率得到6(A),6(D)-dimesitylenesulfonyl-α-CD
  参考文献：
  名称：

  6-Polysubstituted .alpha.-cyclodextrins. Application of Korner's absolute method of isomer determination

  摘要：

  DOI：

  10.1021/ja00275a042

文献信息

• ¹H NMR Study of the Regioisomers of Primary<i>O</i>-Di- and Trisubstituted α-Cyclodextrins
  作者：Yoshihisa Matsui、Masahiko Fujie、Hiroshi Sakate

  DOI：10.1246/bcsj.61.3409

  日期：1988.10

  The regioisomers of bis- and tris[C(6)-O-sulfonylated] α-cyclodextrins were converted in satisfactory yields to the corresponding C(6)-pyridinio derivatives, which afforded the characteristic splitting patterns of 1H NMR signals available for a regioisomer determination. Electrostatic repulsive interactions between the positively charged pyridinio groups play an important role in the remarkable splitting of the 1H NMR signals observed for some regioisomers.

  双[C(6)-O-磺酸酯化]α-环糊精和三[C(6)-O-磺酸酯化]α-环糊精的区域异构体以令人满意的产率转化为相应的C(6)-吡啶铵衍生物，这些衍生物呈现出用于区域异构体鉴定的1H NMR信号的特征分裂模式。正电荷吡啶铵基团之间的电静态排斥相互作用在某些区域异构体中观察到的1H NMR信号显著分裂中起着重要作用。
• Regioselectivity in the formation of di- and tri-6-O-mesitylenesulfonates of α-cyclodextrin
  作者：Keisuke Yoshikiyo、Misaki Shinjo、Yoshihisa Matsui、Tatsuyuki Yamamoto

  DOI：10.1016/j.carres.2014.10.027

  日期：2015.1

  analysis of the reaction products for α-cyclodextrin (α-CD) with mesitylenesulfonyl chloride (MessCl) showed that di- and tri-mesitylenesulfonylation of the primary hydroxy groups of α-CD is regioselective. The reaction of mono-6-O-mesitylenesulfonyl-α-CD with MessCl in pyridine gave less 6(A),6(C)-di-O-mesitylenesulfonyl-α-CD than 6(A),6(B)-di-O-mesitylenesulfonyl-α-CD. The reaction of 6(A),6(D)-d

  定量分析α-环糊精（α-CD）与均三甲磺酰氯（MessCl）的反应产物表明，α-CD伯羟基的二-和三-甲磺酰基磺酰化具有区域选择性。单-6-O-亚甲磺酰基-α-CD与MessCl在吡啶中的反应产生的6（A），6（C）-二-O-亚甲磺酰基-α-CD少于6（A），6（B）-二-O-均三甲磺酰基-α-CD。6（A），6（D）-二-O-亚甲磺酰基-α-CD与MessCl的反应产生较少的6（A），6（B），6（E）-三-O-亚甲磺酰基-α-CD比6（A），6（B），6（D）-三-O-均三甲磺酰基-α-CD。这些结果表明，与吡喃葡萄糖-A（Glc-A）连接的均三甲磺酰基会进一步延迟Glc-C的伯羟基的均三甲磺酰基化。
• Dual Supramolecular Photochirogenesis: Ultimate Stereocontrol of Photocyclodimerization by a Chiral Scaffold and Confining Host
  作者：Cheng Yang、Chenfeng Ke、Wenting Liang、Gaku Fukuhara、Tadashi Mori、Yu Liu、Yoshihisa Inoue

  DOI：10.1021/ja202020x

  日期：2011.9.7

  In contrast to the brilliant success in thermal asymmetric synthesis, precise stereocontrol remains a great challenge in chiral photochemistry because of the lack of effective tools and methodologies for controlling the short-lived, weakly interacting, and highly reactive electronically excited species. In this work, we achieved this goal through the "dual-chiral, dual-supramolecular" photochirogenesis approach, which enabled us to realized dramatic acceleration and perfect stereocontrol in one of the most representative photoreactions. Thus, the [4 + 4] photocyclodimerization of 2-anthracenecarboxylate tethered to an a-cyclodextrin scaffold was accelerated by a gamma-cyclodextrin or cucurbit[8]uril host and gave a single enantiomeric cyclodimer (out of four possible chiral and achiral stereo-isomers) in up to 98% chemical and 99% optical yield.
• 6A6B-, 6A6C-, and 6A6D-disulfonates of .alpha.-cyclodextrin
  作者：Kahee Fujita、Atsuo Matsunaga、Taiji Imoto

  DOI：10.1021/ja00331a061

  日期：1984.9
• 6-Polysubstituted .alpha.-cyclodextrins. Application of Korner's absolute method of isomer determination
  作者：Kahee. Fujita、Hatsuo. Yamamura、Atsuo. Matsunaga、Taiji. Imoto、Kunihide. Mihashi、Toshihiro. Fujioka

  DOI：10.1021/ja00275a042

  日期：1986.7