2^A,3^A,2^D,3^D-dimannoepoxy-β-cyclodextrin | 126188-01-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2^A,3^A,2^D,3^D-dimannoepoxy-β-cyclodextrin
• 英文别名: (1R,3R,5R,6S,8R,10R,11S,13R,14S,16S,17R,19R,21R,22S,24R,26R,27S,29R,31R,32S,34R,35S,37S,38R,40R,41R,42R,43R,44R,45R,46R,48R,49R,50R,51R)-5,10,21,26,31,38,46-heptakis(hydroxymethyl)-2,4,7,9,12,15,18,20,23,25,28,30,33,36,39,47-hexadecaoxadecacyclo[32.3.2.23,6.28,11.213,17.219,22.224,27.229,32.014,16.035,37]henpentacontane-40,41,42,43,44,45,48,49,50,51-decol
• CAS: 126188-01-0
• 化学式: C₄₂H₆₆O₃₃
• 分子量: 1098.97
• InChiKey: FFMMKXOFFGAIHE-MSIPVABCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13
• 重原子数：
  75
• 可旋转键数：
  7
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  498
• 氢给体数：
  17
• 氢受体数：
  33

反应信息

• 作为反应物：
  描述：

  2^A,3^A,2^D,3^D-dimannoepoxy-β-cyclodextrin 在 水 作用下， 反应 144.0h， 以67.9%的产率得到AD-di-altro-β-cyclodextrin
  参考文献：
  名称：

  Preparation of Di-altro-.BETA.-cyclodextrins with Two Altrosides as the Macrocyclic Units through Selective Synthesis of Regioisomers of Di(2-0-mesitylenesulfonyl)-.BETA.-cyclodextrin.

  摘要：

  与报告中使用氧化二丁基锡/三乙胺/对甲苯磺酰氯的方法相比，合成二(2-O-甲磺酰基)-β-环糊精 2-4 的摄取异构体的产率提高了 3、4 倍。由 2-4 制备出二甘露聚氧乙烯醚-β-环糊精的 Regioisomers 5-7，并分别转化为相应的以两个altrosides 作为大环单元的二altro-β-环糊精（8-10）。通过核磁共振研究了二-对半-β-环糊精中altroside部分的构象，发现altroside会根据其是否为大环成员以及在环中的位置而改变其构象。

  DOI：

  10.1248/cpb.45.631
• 作为产物：
  描述：

  (1R,2R,28R,29S,30S,31R,33R,35S,36R,38R,40S,41R,43R,45S,46R,48R,50S,51R,54S,55R,57R,59S,60R,62R,64R,65R,66R,67R,68S,69R,70R,71R,72R,73R,74R)-31,36,41,46,51,55,60-heptakis(hydroxymethyl)-4,4,15,15,26,26-hexaoxo-3,27,32,34,37,39,42,44,47,49,52,53,56,58,61,63-hexadecaoxa-4lambda6,15lambda6,26lambda6-trithiatetradecacyclo[28.22.11.25,8.222,25.235,38.240,43.245,48.254,57.259,62.12,50.110,14.116,20.013,17.028,33]octaconta-5,7,10(78),11,13,16,18,20(77),22,24,75,79-dodecaene-29,64,65,66,67,68,69,70,71,72,73,74-dodecol 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 30.0h， 以93%的产率得到2^A,3^A,2^D,3^D-dimannoepoxy-β-cyclodextrin
  参考文献：
  名称：

  Regioselective 2A,2D-disulfonyl capping of β-cyclodextrin for practical bifunctionalization on the secondary hydroxyl face

  摘要：

  A useful technique to bifunctionalize the secondary hydroxyl face of P-cyclodextrin is described. Regioselective 2(A),2(D)-disulfonylation of beta -cyclodextrin was achieved by reacting P-cyclodextrin with a combination of a novel disulfonyl imidazole reagent and molecular sieves in DMF. The resulting disulfonate was converted to 2(A),3(A),2(D),3(D)-dimannoepoxy-beta -C, cyclodextrin and 3(A),3(D)-diamino-3(A),3(D)-dideoxy-(2(A) S,3(A)S) (2(D)S,3(A)S)-beta -cyclodextrin, which contains two functional groups on the periphery of the molecule. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01025-5

文献信息

• 2^A,2^B-, 2^A,2^C-, and 2^A,2^D-Bis-<i>O</i>-(<i>p</i>-tolylsulfonyl)-β-cyclodextrins
  作者：Kahee Fujita、Takashi Ishizu、Kyoko Oshiro、Ken-ichi Obe

  DOI：10.1246/bcsj.62.2960

  日期：1989.9

  A mixture of the title ditosylates was prepared by the reaction of β-cyclodextrin with dibutyltin oxide and tosyl chloride. Each ditosylate was isolated by reversed-phase column chromatography and the structure was assigned on the basis of conversion into a known compound or hydrolysis with Taka amylase A.

  通过β-环糊精与氧化二丁基锡和甲苯磺酰氯反应制备标题二甲苯磺酸盐的混合物。通过反相柱色谱分离每种二甲苯磺酸酯，并根据转化为已知化合物或用 Taka 淀粉酶 A 水解来确定结构。
• Construction of a Fused Polycyclic Wall within the Cyclodextrin Belt To Ensure a Distorted Cavity: An Unusualtrans-Diequatorial Ring-Opening Reaction of Cyclodextrin Epoxide Rings
  作者：Kahee Fujita、Toshihiro Fujioka、Hideaki Shimada、Kazuko Ohta、Akitoshi Yoshino、Yuji Okabe、Makoto Fukudome、De-Qi Yuan

  DOI：10.1002/ejoc.200400162

  日期：2004.7

  attack by 3X−1-OH at the 2X-C position of the epoxide is observed. The reaction affords the apparent trans-diequatorial products and ensures an efficient construction of fused heterocycles within the cyclodextrin belt. In the case of 2I,3I:2II,3II-di-manno-epoxy-β-cyclodextrin, a tandem-type reaction is initiated by the attack by the 3VII-OH group at the 2I-C position to generate a fused pentacycle

  在 2X,3X-甘露糖环氧化物的亲核开环反应中，进入的亲核试剂几乎完全攻击环氧化物的 3X-C 位置。然而，当分子内羟基充当亲核试剂时，观察到非常不寻常但非常有趣的反向区域选择性，即仅观察到 3X-1-OH 在环氧化物的 2X-C 位置处的攻击。该反应提供明显的反式二赤道产物并确保在环糊精带内有效构建稠合杂环。在 2I,3I:2II,3II-di-manno-epoxy-β-cyclodextrin 的情况下，串联型反应由 2I-C 位置的 3VII-OH 基团的攻击引发，生成稠合的五环。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Practical and convenient modifications of the A,C-secondary hydroxyl face of cyclodextrins
  作者：Katsunori Teranishi

  DOI：10.1016/s0040-4020(03)00259-x

  日期：2003.3

  A practical and convenient method for the preparation of α-, β-, and γ-cyclodextrin derivatives, in which the secondary hydroxyl faces of A- and C-glucose units are regioselectively modified, has been developed. Reactions of α-, β-, and γ-cyclodextrins with 1,4-dibenzoylbenzene-3′,3″-disulfonyl imidazole in N,N-dimethylformamide in the presence of molecular sieves regioselectively afforded the corresponding

  已经开发了一种实用且方便的制备α-，β-和γ-环糊精衍生物的方法，其中对A-和C-葡萄糖单元的仲羟基面进行了区域选择性修饰。α-，β-的反应，并用1,4-二苯甲酰基苯-3'，3“-disulfonyl咪唑在γ环糊精Ñ，Ñ二甲基甲酰胺在分子筛的存在区域选择性得到相应的环状2甲，2 Ç - （1，4-二苯甲酰基苯-3'，3″-二磺酰基）-环糊精。随后用氢氧化钠或氨水处理磺酰化的环糊精，得到相应的2 A，3 A：2 C，3 C-di-manno-epoxy-cyclodextrins或3 A，3 C -diamino-3 A，3 C -dideoxy-（2 A S，2 C S，3 A S，3 C S）-环糊精作为环糊精进一步功能化的重要中间体。
• Regioselective 2A,2D-disulfonyl capping of β-cyclodextrin for practical bifunctionalization on the secondary hydroxyl face
  作者：Katsunori Teranishi

  DOI：10.1016/s0040-4039(01)01025-5

  日期：2001.8

  A useful technique to bifunctionalize the secondary hydroxyl face of P-cyclodextrin is described. Regioselective 2(A),2(D)-disulfonylation of beta -cyclodextrin was achieved by reacting P-cyclodextrin with a combination of a novel disulfonyl imidazole reagent and molecular sieves in DMF. The resulting disulfonate was converted to 2(A),3(A),2(D),3(D)-dimannoepoxy-beta -C, cyclodextrin and 3(A),3(D)-diamino-3(A),3(D)-dideoxy-(2(A) S,3(A)S) (2(D)S,3(A)S)-beta -cyclodextrin, which contains two functional groups on the periphery of the molecule. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Preparation of Di-altro-.BETA.-cyclodextrins with Two Altrosides as the Macrocyclic Units through Selective Synthesis of Regioisomers of Di(2-0-mesitylenesulfonyl)-.BETA.-cyclodextrin.
  作者：Kazuko OHTA、Kahee FUJITA、Hideaki SHIMADA、Yoshihiro IKEGAMI、Yasuyoshi NOGAMI、Toshitaka KOGA

  DOI：10.1248/cpb.45.631

  日期：——

  Regioisomers of di(2-O-mesitylenesulfonyl)-β-cyclodextrin 2-4 were synthesized in 3, 4 times larger yields compared to those of the reported method using dibutyltin oxide/triethylamine/p-toluenesulfonyl chloride. Regioisomers of di-mannoepoxy-β-cyclodextrin 5-7 were prepared from 2-4 and converted to the corresponding di-altro-β-cyclodextrins (8-10) with two altrosides as macrocyclic units, respectively. Conformations of the altrose parts of di-altro-β-cyclodextrins were investigated by NMR, and the altroside was found to change its conformation depending on whether or not it is a member of the macrocyclic ring and its position in the ring.

  与报告中使用氧化二丁基锡/三乙胺/对甲苯磺酰氯的方法相比，合成二(2-O-甲磺酰基)-β-环糊精 2-4 的摄取异构体的产率提高了 3、4 倍。由 2-4 制备出二甘露聚氧乙烯醚-β-环糊精的 Regioisomers 5-7，并分别转化为相应的以两个altrosides 作为大环单元的二altro-β-环糊精（8-10）。通过核磁共振研究了二-对半-β-环糊精中altroside部分的构象，发现altroside会根据其是否为大环成员以及在环中的位置而改变其构象。