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Volumn 63, Issue 3-4, 2009, Pages 373-378

Facile direct acylation and acyl migration of β-cyclodextrin on the secondary hydroxyl face

Author keywords

Cyclodextrin; Acyl migration; Acylation; N benzoylimidazole

Indexed keywords


EID: 63049137736     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-008-9511-8     Document Type: Article
Times cited : (4)

References (32)
  • 1
    • 0001136532 scopus 로고
    • Biomimetic chemistry
    • R Breslow 1994 Biomimetic chemistry Pure. Appl. Chem. 66 1573
    • (1994) Pure. Appl. Chem. , vol.66 , pp. 1573
    • Breslow, R.1
  • 2
    • 2842610709 scopus 로고
    • Biomimetic chemistry and artificial enzymes: Catalysis by design
    • R Breslow 1995 Biomimetic chemistry and artificial enzymes: catalysis by design Acc. Chem. Res. 28 146
    • (1995) Acc. Chem. Res. , vol.28 , pp. 146
    • Breslow, R.1
  • 3
    • 1842582944 scopus 로고    scopus 로고
    • Biomimetic reactions catalyzed by cyclodextrins and their derivatives
    • R Breslow SD Dong 1998 Biomimetic reactions catalyzed by cyclodextrins and their derivatives Chem. Rev. 98 1997 2011
    • (1998) Chem. Rev. , vol.98 , pp. 1997-2011
    • Breslow, R.1    Dong, S.D.2
  • 5
    • 0001354595 scopus 로고    scopus 로고
    • Industrial applications of cyclodextrins
    • AR Hedges 1998 Industrial applications of cyclodextrins Chem. Rev. 98 2035 2044
    • (1998) Chem. Rev. , vol.98 , pp. 2035-2044
    • Hedges, A.R.1
  • 6
    • 0032119526 scopus 로고    scopus 로고
    • Cyclodextrin drug carrier systems
    • K Uekama F Hirayama T Irie 1998 Cyclodextrin drug carrier systems Chem. Rev. 98 2045 2076
    • (1998) Chem. Rev. , vol.98 , pp. 2045-2076
    • Uekama, K.1    Hirayama, F.2    Irie, T.3
  • 7
    • 37749023584 scopus 로고    scopus 로고
    • Supramolecular enantiodifferentiating photoisomerization of cyclooctene with modified beta-cyclodextrins: Critical control by a host structure
    • Lu, R.H., Yang, C., Cao, Y.J., Wang, Z.Z., Wada, T., Jiao W., Mori, T., Inoue, Y.: Supramolecular enantiodifferentiating photoisomerization of cyclooctene with modified beta-cyclodextrins: critical control by a host structure. Chem. Commun. 374-376 (2008)
    • (2008) Chem. Commun. , vol.374-376
    • Lu, R.H.1    Yang, C.2    Cao, Y.J.3    Wang, Z.Z.4    Wada, T.5    Jiao, W.6    Mori, T.7    Inoue, Y.8
  • 8
    • 33750025006 scopus 로고    scopus 로고
    • Entropy-controlled supramolecular photochirogenesis: Enantiodifferentiating Z-E photoisomerization of cyclooctene included and sensitized by permethylated 6-O-modified-beta-cyclodextrins
    • G Fukuhara T Mori T Wada Y Inoue 2006 Entropy-controlled supramolecular photochirogenesis: enantiodifferentiating Z-E photoisomerization of cyclooctene included and sensitized by permethylated 6-O-modified-beta-cyclodextrins J. Org. Chem. 71 8233 8243
    • (2006) J. Org. Chem. , vol.71 , pp. 8233-8243
    • Fukuhara, G.1    Mori, T.2    Wada, T.3    Inoue, Y.4
  • 9
    • 33745911941 scopus 로고    scopus 로고
    • Asymmetric photochemistry with native and modified cyclodextrins
    • LH Tong RH Lu Y Inoue 2006 Asymmetric photochemistry with native and modified cyclodextrins Prog. Chem. 18 533 541
    • (2006) Prog. Chem. , vol.18 , pp. 533-541
    • Tong, L.H.1    Lu, R.H.2    Inoue, Y.3
  • 10
    • 25144459418 scopus 로고    scopus 로고
    • Entropy-controlled supramolecular photochirogenesis: Enantiodifferentiating Z-E photoisomerization of cyclooctene included and sensitized by permethylated 6-O-benzoyl-b-cyclodextrin
    • Fukuhara, G., Mori, T., Wada, T., Inoue, Y.: Entropy-controlled supramolecular photochirogenesis: enantiodifferentiating Z-E photoisomerization of cyclooctene included and sensitized by permethylated 6-O-benzoyl-b- cyclodextrin. Chem. Commun. 4199-4201 (2005)
    • (2005) Chem. Commun. , vol.4199-4201
    • Fukuhara, G.1    Mori, T.2    Wada, T.3    Inoue, Y.4
  • 11
  • 12
    • 33947335958 scopus 로고
    • Acceleration of phenyl ester cleavage by cycloamyloses. A model for enzymic specificity
    • RL Vanetten JF Sebastian GA Clowes ML Bender 1967 Acceleration of phenyl ester cleavage by cycloamyloses. A model for enzymic specificity J. Am. Chem. Soc. 89 3242 3253
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 3242-3253
    • Vanetten, R.L.1    Sebastian, J.F.2    Clowes, G.A.3    Bender, M.L.4
  • 14
    • 0025360578 scopus 로고
    • Artificial enzymes: Synthesis of imidazole substituted at C(2) of beta-cyclodextrin as an efficient enzyme model of chymotrypsin
    • Rama Rao, K., Srinivasan, T.N., Bhanumathi, N., Sattur, P.B.: Artificial enzymes: synthesis of imidazole substituted at C(2) of beta-cyclodextrin as an efficient enzyme model of chymotrypsin. J. Chem. Soc. Chem. Commun. 10 (1990)
    • (1990) J. Chem. Soc. Chem. Commun. , vol.10
    • Rama Rao, K.1    Srinivasan, T.N.2    Bhanumathi, N.3    Sattur, P.B.4
  • 15
    • 0001119930 scopus 로고    scopus 로고
    • Methods for selective modifications of cyclodextrins
    • AR Khan P Forgo KJ Stine VT D'Souza 1998 Methods for selective modifications of cyclodextrins Chem. Rev. 98 1977 1996
    • (1998) Chem. Rev. , vol.98 , pp. 1977-1996
    • Khan, A.R.1    Forgo, P.2    Stine, K.J.3    D'Souza, V.T.4
  • 16
    • 0000453735 scopus 로고
    • Selective sulfonation of a secondary hydroxyl group of beta-cyclodextrin
    • A Ueno R Breslow 1982 Selective sulfonation of a secondary hydroxyl group of beta-cyclodextrin Tetrahedron Lett. 23 3451 3454
    • (1982) Tetrahedron Lett. , vol.23 , pp. 3451-3454
    • Ueno, A.1    Breslow, R.2
  • 17
    • 0025328330 scopus 로고
    • A convenient method for functionalization of the 2-position of cyclodextrins
    • D Rong VT D'Souza 1990 A convenient method for functionalization of the 2-position of cyclodextrins Tetrahedron Lett. 31 4275 4278
    • (1990) Tetrahedron Lett. , vol.31 , pp. 4275-4278
    • Rong, D.1    D'Souza, V.T.2
  • 18
    • 0037436002 scopus 로고    scopus 로고
    • Regioselective sulfonylation at O-2 of cyclomaltoheptaose with 1-(p-tolylsulfonyl)-(1H)-1, 2, 4-triazole
    • H Law I Baussanne JM Garc Fernandez J Defaye 2003 Regioselective sulfonylation at O-2 of cyclomaltoheptaose with 1-(p-tolylsulfonyl)-(1H)-1, 2, 4-triazole J. Carbohydr. Res. 338 451 453
    • (2003) J. Carbohydr. Res. , vol.338 , pp. 451-453
    • Law, H.1    Baussanne, I.2    Garc Fernandez, J.M.3    Defaye, J.4
  • 19
    • 0032372706 scopus 로고    scopus 로고
    • Efficient regioselective synthesis of mono-2-O-sulfonyl-cyclodextrins by the combination of sulfonyl imidazole and molecular sieves
    • K Teranishi K Watanabe M Hisamatsu T Yamada 1998 Efficient regioselective synthesis of mono-2-O-sulfonyl-cyclodextrins by the combination of sulfonyl imidazole and molecular sieves J. Carbohydr. Chem. 17 489 494
    • (1998) J. Carbohydr. Chem. , vol.17 , pp. 489-494
    • Teranishi, K.1    Watanabe, K.2    Hisamatsu, M.3    Yamada, T.4
  • 20
    • 0034698222 scopus 로고    scopus 로고
    • Practicable regiospecific bifunctionalization on the secondary face of alpha- and beta-cyclodextrins
    • Teranishi, K.: Practicable regiospecific bifunctionalization on the secondary face of alpha- and beta-cyclodextrins. Chem. Commun. 1255-1256 (2000)
    • (2000) Chem. Commun. , vol.1255-1256
    • Teranishi, K.1
  • 21
    • 0034596464 scopus 로고    scopus 로고
    • C-disulfonation of β-cyclodextrin
    • C-disulfonation of β-cyclodextrin Tetrahedron Lett. 41 7085 7088
    • (2000) Tetrahedron Lett. , vol.41 , pp. 7085-7088
    • Teranishi, K.1
  • 22
    • 0035817363 scopus 로고    scopus 로고
    • D-disulfonyl capping of β-cyclodextrin for practical bifunctionalization on the secondary hydroxyl face
    • D-disulfonyl capping of β-cyclodextrin for practical bifunctionalization on the secondary hydroxyl face Tetrahedron Lett. 42 5477 5480
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5477-5480
    • Teranishi, K.1
  • 23
    • 33750629349 scopus 로고    scopus 로고
    • A facile sulfonylation method enabling direct syntheses of per(2-O-sulfonyl)-β-cyclodextrins
    • H Yu A Teramoto M Fukudome RG Xie DQ Yuan K Fujita 2006 A facile sulfonylation method enabling direct syntheses of per(2-O-sulfonyl)-β- cyclodextrins Tetrahedron Lett. 47 8837 8840
    • (2006) Tetrahedron Lett. , vol.47 , pp. 8837-8840
    • Yu, H.1    Teramoto, A.2    Fukudome, M.3    Xie, R.G.4    Yuan, D.Q.5    Fujita, K.6
  • 24
    • 33947494920 scopus 로고    scopus 로고
    • Facile one-step synthesis of mono-2-(p-tolylsulfonyl)-β-cyclodextrin under aqueous conditions
    • Strerath, M., Meng, M., Kubik, S.: Facile one-step synthesis of mono-2-(p-tolylsulfonyl)-β-cyclodextrin under aqueous conditions. Synthesis 348-350 (2007)
    • (2007) Synthesis , vol.348-350
    • Strerath, M.1    Meng, M.2    Kubik, S.3
  • 25
    • 0028786058 scopus 로고
    • Convenient preparation of monoacylated β-cyclodextrin (cyclomaltoheptaose) on the secondary hydroxyl side
    • AY Hao LH Tong FS Zhang XM Gao 1995 Convenient preparation of monoacylated β-cyclodextrin (cyclomaltoheptaose) on the secondary hydroxyl side J. Carbohydr. Res. 277 333 337
    • (1995) J. Carbohydr. Res. , vol.277 , pp. 333-337
    • Hao, A.Y.1    Tong, L.H.2    Zhang, F.S.3    Gao, X.M.4
  • 26
  • 28
    • 85023536030 scopus 로고
    • An improved synthesis of methyl 2-O-benzoyl-4,6-O-benzylidene-α-D- altropyranoside
    • Holder, N.L., Fraser-Reid, B.: An improved synthesis of methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-altropyranoside. Synthesis 83 (1972)
    • (1972) Synthesis , vol.83
    • Holder, N.L.1    Fraser-Reid, B.2
  • 29
    • 50949132507 scopus 로고    scopus 로고
    • A convenient and economic method for the synthesis of mono-2-tosyl-β-cyclodextrin
    • ZZ Wang GY He RH Lu 2008 A convenient and economic method for the synthesis of mono-2-tosyl-β-cyclodextrin Monatsh. Chem. 139 1109 1111
    • (2008) Monatsh. Chem. , vol.139 , pp. 1109-1111
    • Wang, Z.Z.1    He, G.Y.2    Lu, R.H.3
  • 30
    • 58549108768 scopus 로고    scopus 로고
    • One-step regioselective green synthesis of 2,3-mannoepoxy-β- cyclodextrin under aqueous conditions
    • doi: 10.1007/s00706-008-0010-9
    • Wang, Z.Z., Jiao, W., He, G.Y., Lu, R.H.: One-step regioselective green synthesis of 2,3-mannoepoxy-β-cyclodextrin under aqueous conditions. Monatsh. Chem. (2008). doi: 10.1007/s00706-008-0010-9
    • (2008) Monatsh. Chem.
    • Wang, Z.Z.1    Jiao, W.2    He, G.Y.3    Lu, R.H.4
  • 31
    • 0034625164 scopus 로고    scopus 로고
    • Selective disruption of protein aggregation by cyclodextrin dimers
    • DK Leung ZW Yang R Breslow 2000 Selective disruption of protein aggregation by cyclodextrin dimers Proc. Natl. Acad. Sci. USA 97 5050 5053
    • (2000) Proc. Natl. Acad. Sci. USA , vol.97 , pp. 5050-5053
    • Leung, D.K.1    Yang, Z.W.2    Breslow, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.