- REGIOSELECTIVE SULFONATION OF A SECONDARY HYDROXYL GROUP OF CYCLODEXTRINS
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A new and convenient procedure has been developed for the regioselective tosylation of a C-2 hydroxyl group of cyclodextrins via cyclic tin intermediate.
- Murakumi, Teiichi,Harata, Kazuaki,Morimoto, Satoshi
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- Supramolecular dioxygen receptors composed of an anionic water-soluble porphinatoiron(ii) and cyclodextrin dimers
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Three types of per-O-methylated β-cyclodextrin dimers, Im2CD, Im3NHCD and Py3NHCD, were prepared as globin models. Im2CD was synthesized by the condensation reaction of mono(2A-amino)-per-O-methylated β-cyclodextrin with 3-(1H-imidazol-1-yl)pen
- Kano, Koji,Chimoto, Syoichi,Tamaki, Mariko,Itoh, Yoshiki,Kitagishi, Hiroaki
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- Facile one-step synthesis of mono-2-(p-tolylsulfonyl)-β-cyclodextrin under aqueous conditions
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A new and convenient method is presented for the synthesis of mono-2-(p-tolylsulfonyl)-β-cyclodextrin under aqueous conditions that does not require large amounts of polar organic solvents such as DMF, metal-containing reagents such as dibutyltin oxide, o
- Strerath, Michael,Meng, Martin,Kubik, Stefan
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- SELECTIVE SULFONATION OF A SECONDARY HYDROXYL GROUP OF β-CYCLODEXTRIN
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Tosyletion of the secondary side of β-cyclodextrin, which has previously been incorrectly reported, can be achived by tosyl transfer from 3-nitrophenyl toluenesulfonate to the C-2 hydroxyl of the cyclodextrin.
- Ueno, Akihiko,Breslow, Ronald
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- Preparation and self-inclusion properties of p-xylylenediamine-modified β-cyclodextrins: dependence on the side of modification
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β-Cyclodextrin (β-CDx) derivatives modified with p-xylylenediamine at the 3-position, mono-3-deoxy-3-[4-(aminomethyl)benzylamino]-β-CDx (1; β-CDx-3-p-xylylenediamine) was prepared by the reaction of β-CDx-2,3-manno-epoxide with p-xylylenediamine. The circ
- Park, Kwanghee Koh,Kim, Young Sin,Lee, Soo Yeon,Song, Hee Eun,Park, Joon Woo
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- A convenient and economic method for the synthesis of mono-2-tosyl-β- cyclodextrin
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A convenient and economic method for the regioselective synthesis of mono-2-tosyl-β-cyclodextrin was achieved by using the combination of N-tosylimidazole and carbonate buffer in DMF, the reaction does not require strict anhydrous or specific basic cataly
- Wang, Zhi-Zhong,He, Guang-Yun,Lu, Run-Hua
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- Disparate orientation of [1]rotaxanes
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A novel [1]rotaxane 2 has been synthesized employing a 4-methyl-benzenesulfonyl and an azobenzene modified β-cyclodextrin (β-CyD) at the 2 position, through self-inclusion complexation and Suzuki-coupling capping in aqueous solution. Disparate absorption,
- Ma, Xiang,Wang, Qiaochun,Tian, He
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- A Cyclodextrin-Based Photoresponsive Molecular Gate that Functions Independently of Either Solvent or Potentially Competitive Guests
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The photoinduced interconversion between cinnamido-substituted cyclodextrins constitutes a gating switch through which the substituent moves to open or block access to the cyclodextrin cavity. Most unusually for a cyclodextrin-based device, the operation of this gate is solvent-independent and unaffected by potentially competitive guests. It occurs in MeOH and DMSO, as well as in water. This contrasts with other cyclodextrin inclusion phenomena that are usually driven by hydrophobic effects and limited to aqueous media. Shut the gate: A very unusual cyclodextrin gate has been found that opens and shuts photochemically, instead of being operated by hydrophobic effects and therefore limited to aqueous media.
- Loh, Ka-Heng,Smith, Nicole M.,Onagi, Hideki,Lincoln, Stephen F.,Easton, Christopher J.
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- 6-TIPS-β-Cyclodextrin-Modified Fe3O4 for Facile Enantioseparation of 1-(1-Naphthyl)ethylamine
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A new type of chiral magnetic nanoparticle was prepared from covalently linked magnetic nanoparticles (Fe3O4) and heptakis-(6-O-triisopropylsilyl)-β-cyclodextrin (6-TIPS-β-CD). The resulting selectors (TIPS-β-CD-MNPs) combined the good magnetic properties Fe3O4 and efficient chiral recognition ability of 6-TIPS-β-CD. The enantioselectivity of TIPS-β-CD-MNPs towards 1-(1-naphthyl)ethylamine was six times higher than that of the parent β-CD modified Fe3O4 particles.
- Wang, Lu,Liang, Xiang-Yong,Ding, Li-Sheng,Zhang, Sheng,Li, Bang-Jing
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supporting information
p. 3513 - 3519
(2016/12/26)
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- Direct regioselective esterification at O-2 of β- Cyclodextrin and hydrolysis by neighboring-group participation
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A simple and efficient strategy for direct regioselective esterification at O-2 of β-cyclodextrin was developed by using the combination of N,N?-carbonyldiimidazole and carbonate buffer in 1,4-dioxane, which does not require large amounts of polar organic solvents such as DMF, toxic solvents such as CH3CN, or flammable bases such as NaH. Moreover, their hydrolyses by neighboring-group participation were observed. Mono-2-tosyl- β-cyclodextrin was liable to epoxidation, while mono-2-(p-methylbenzoyl)- β- cyclodextrin liable to isomerization. They had different mechanisms of hydrolysis.
- Wang, Zhi-Zhong,Ma, Xuan-Ping,Wei, Xiao-Gang
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experimental part
p. 1562 - 1568
(2012/05/21)
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- Efficient regioselective functionalizations of cyclodextrins carried out under microwaves or power ultrasound
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Regioselective syntheses of differently functionalized cyclodextrins (CDs) were efficiently carried out under ultrasound or microwave irradiation. 6I-Deoxy-6I-thio-β-CD, 6I-deoxy-6I-formyl-β-CD, and 6A,6D-dideoxy-6A,6D-dithio-β-CD were prepared under microwave irradiation. A new rapid and efficient ultrasound-assisted protocol is described for the synthesis of 3I-azido-3I-deoxy-α, -β, and -γ-CD by selective tosylation followed by azide substitution.
- Martina, Katia,Trotta, Francesco,Robaldo, Bruna,Belliardi, Nikka,Jicsinszky, László,Cravotto, Giancarlo
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p. 9185 - 9189
(2008/09/18)
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- MONOTOSYLATED α-AND β-CYCLODEXTRINS PREPARED IN AN ALKALINE AQUEOUS SOLUTION
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In order to establish the tosylated positions of α- and β-cyclodextrins, 13C-nmr spectra for the monotosyl-derivatives prepared in an alkaline aqueous solution were examined and determined to be in the 6-position of one glucose unit for β-cyclodextrin and
- Takahashi, Keiko,Hattori, Kenjiro,Toda, Fujio
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p. 3331 - 3334
(2007/10/02)
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