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Volumn 29, Issue 2, 2010, Pages 76-83

N-bromosuccinimide-mediated conversion of allyl glycosides to glycosyl hemiacetals

Author keywords

Allyl glycoside; Glycosyl hemiacetal; Hydrolysis; N bromosuccinimide

Indexed keywords


EID: 77951575016     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328301003664887     Document Type: Article
Times cited : (7)

References (45)
  • 2
    • 0000387792 scopus 로고
    • Chemically synthesized oligosaccharides, 1994. A searchable table of glycosidic linkages
    • Barresi,F.; Hindsgaul, O. Chemically synthesized oligosaccharides, 1994. A searchable table of glycosidic linkages. J. Carbohydr. Chem. 1995, 14, 1043-1087;
    • (1995) J. Carbohydr. Chem. , vol.14 , pp. 1043-1087
    • Barresi, F.1    Hindsgaul, O.2
  • 3
    • 61849111654 scopus 로고    scopus 로고
    • New principles for glycoside-bond formation
    • Zhu, X.; Schmidt, R.R. New principles for glycoside-bond formation. Angew. Chem. Int. Ed. Engl. 2009, 48, 1900-1934.
    • (2009) Angew. Chem. Int. Ed. Engl. , vol.48 , pp. 1900-1934
    • Zhu, X.1    Schmidt, R.R.2
  • 5
    • 0030761432 scopus 로고    scopus 로고
    • Direct glycosylations with 1-hydroxy glycosyl donors using trifluoromethanesulfonic anhydride and diphenyl sulfoxide
    • Garcia, B.A.; Poole, J.L.; Gin, D.Y. Direct glycosylations with 1-hydroxy glycosyl donors using trifluoromethanesulfonic anhydride and diphenyl sulfoxide. J. Am . Chem . 2. Soc. 1997, 119, 7597-7598;
    • (1997) J. Am . Chem . 2. Soc. , vol.119 , pp. 7597-7598
    • Garcia, B.A.1    Poole, J.L.2    Gin, D.Y.3
  • 6
    • 0034630905 scopus 로고    scopus 로고
    • Dehydrative glycosylation with activated diphenyl sulfonium reagents Scope, mode of C(1)-hemiacetal activation, and detection of reactive glycosyl intermediates
    • Garcia, B.A.; Gin, D.Y. Dehydrative glycosylation with activated diphenyl sulfonium reagents. Scope, mode of C(1)-hemiacetal activation, and detection of reactive glycosyl intermediates. J. Am. Chem. Soc. 2000, 122, 4269-4279;
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 4269-4279
    • Garcia, B.A.1    Gin, D.Y.2
  • 7
    • 0034644003 scopus 로고    scopus 로고
    • Synthesis of glycosyl-1-phosphates via dehydrative glycosy-lation
    • Garcia, B.A.; Gin, D.Y. Synthesis of glycosyl-1-phosphates via dehydrative glycosy-lation. Org. Lett. 2000, 2, 2135-2138.
    • (2000) Org. Lett. , vol.2 , pp. 2135-2138
    • Garcia, B.A.1    Gin, D.Y.2
  • 10
    • 0034631777 scopus 로고    scopus 로고
    • Methods of synthesis of glycosyl fluorides
    • DOI 10.1016/S0008-6215(99)00324-9, PII S0008621599003249
    • Yokoyama, M. Methods of synthesis of glycosyl fluorides. Carbohydr. Res. 2000, 327, 5-14. (Pubitemid 30624995)
    • (2000) Carbohydrate Research , vol.327 , Issue.1-2 , pp. 5-14
    • Yokoyama, M.1
  • 11
    • 84986650768 scopus 로고
    • Glycoside bond formation via anomeric O-alkylation: How many protective groups are required?
    • Schmidt, R.R.; Klotz, W. Glycoside bond formation via anomeric O-alkylation: how many protective groups are required? Synlett 1991, 168-170;
    • (1991) Synlett , pp. 168-170
    • Schmidt, R.R.1    Klotz, W.2
  • 12
    • 0023203242 scopus 로고
    • The total synthesis of (+)-payllanthostatin 2
    • Smith, A.B. III; Hale, K.J.; Vaccaro, H.A. The total synthesis of (+)-payllanthostatin 2. Tetrahedron Lett. 1987, 28, 5591-5594.
    • (1987) Tetrahedron Lett , vol.28 , pp. 5591-5594
    • Smith III, A.B.1    Hale, K.J.2    Vaccaro, H.A.3
  • 13
    • 34948906776 scopus 로고    scopus 로고
    • Synthesis of the glycosyl lactol moiety of halichoblelide
    • DOI 10.1016/j.tet.2007.08.100, PII S0040402007015402
    • Satoh, Y.; Nakahata, T.; Kuwahara, S. Synthesis of the glycosyl lactol moiety of halichoblelide.Tetrahedron 2007, 63, 11733-11737. (Pubitemid 47532154)
    • (2007) Tetrahedron , vol.63 , Issue.47 , pp. 11733-11737
    • Satoh, Y.1    Nakahata, T.2    Kuwahara, S.3
  • 14
    • 49549143786 scopus 로고
    • Coupure sélective par l'hydrazine des groupements acétyles anomères de résidus glycosyles acétylés
    • Excoffier, G.; Gagnaire, D.; Utille, J.-P. Coupure sélective par l'hydrazine des groupements acétyles anomères de résidus glycosyles acétylés. Carbohydr. Res. 1975, 39, 368-373.
    • (1975) Carbohydr. Res. , vol.39 , pp. 368-373
    • Excoffier, G.1    Gagnaire, D.2    Utille, J.-P.3
  • 15
    • 0034923058 scopus 로고    scopus 로고
    • Regioselective 1-O-acyl hydrolysis of peracylated glycopyranoses by mercuric chloride and mercuric oxide
    • Sambaiah, T.; Fanwick, P.E.; Cushman, M. Regioselective 1-O-acyl hydrolysis of peracylated glycopyranoses by mercuric chloride and mercuric oxide. Synthesis 2001, 1450-1452. (Pubitemid 32701803)
    • (2001) Synthesis , Issue.10 , pp. 1450-1452
    • Sambaiah, T.1    Fanwick, P.E.2    Cushman, M.3
  • 18
    • 0003073092 scopus 로고
    • 5-α-D-Manp-(1→} a manno isomer of cyclomaltohexaose
    • 5-α-D-Manp-(1→}, a manno isomer of cyclomaltohexaose. Carbohydr. Res. 1989, 192, 131-146;
    • (1989) Carbohydr. Res. , vol.192 , pp. 131-146
    • Mori, M.1    Ito, Y.2    Ogawa, T.3
  • 19
    • 0000584917 scopus 로고
    • A convergent and stereocontrolled synthetic route to the core pentasaccharide structure of asparagine-linked glycoproteins
    • Dan, A.; Ito, Y.; Ogawa, T. A convergent and stereocontrolled synthetic route to the core pentasaccharide structure of asparagine-linked glycoproteins. J. Org. Chem. 1995, 60, 4680-4681.
    • (1995) J. Org. Chem. , vol.60 , pp. 4680-4681
    • Dan, A.1    Ito, Y.2    Ogawa, T.3
  • 20
    • 0036138065 scopus 로고    scopus 로고
    • A mild and environmentally benign synthetic protocol for catalytic hydrolysis of thioglycosides
    • Bujar Barua, P.M.; Sahu, P.R.; Mondal, E.; Bose, G.; Khan, A.T. A mild and environmentally benign synthetic protocol for catalytic hydrolysis of thioglycosides. Synlett 2002, 81-84. (Pubitemid 34048778)
    • (2002) Synlett , Issue.1 , pp. 81-84
    • Bujar Barua, P.M.1    Sahu, P.R.2    Mondal, E.3    Bose, G.4    Khan, A.T.5
  • 21
    • 0013324618 scopus 로고
    • A general method based on the use of N-bromosuccinimide for removal of the thiophenyl group at the anomeric position to generate a reducing sugar with the original protecting groups still present
    • Motawia, M.S.; Marcussan, J.; Moeller, B.L. A general method based on the use of N-bromosuccinimide for removal of the thiophenyl group at the anomeric position to generate a reducing sugar with the original protecting groups still present. J. Carbohydr. Chem. 1995, 14, 1279-1294;
    • (1995) J. Carbohydr. Chem. , vol.14 , pp. 1279-1294
    • Motawia, M.S.1    Marcussan, J.2    Moeller, B.L.3
  • 22
    • 0032388363 scopus 로고    scopus 로고
    • A New Efficient Method for Catalytic Hydrolysis of Thioglycoside
    • Uchiro, H.; Wakiyama, Y.; Mukaiyama, T. A new efficient method for catalytic hydrolysis of thioglycoside. Chem. Lett. 1998, 567-568; (Pubitemid 128131958)
    • (1998) Chemistry Letters , Issue.7 , pp. 567-568
    • Uchiro, H.1    Wakiyama, Y.2    Mukaiyama, T.3
  • 23
    • 33845551357 scopus 로고
    • A mild and general method for the synthesis of O-glycosides
    • Nicolaou, K.C.; Seitz, S.P.; Papahatjis, D.P. A mild and general method for the synthesis of O-glycosides. J. Am . Chem . Soc . 1983, 105, 2430-2434.
    • (1983) J. Am . Chem . Soc . , vol.105 , pp. 2430-2434
    • Nicolaou, K.C.1    Seitz, S.P.2    Papahatjis, D.P.3
  • 24
    • 1242292330 scopus 로고    scopus 로고
    • Chloramine-T-mediated chemoselective hydrolysis of thioglycosides into glycosyl hemiacetals under neutral conditions
    • DOI 10.1016/j.carres.2003.12.020
    • Misra, A.K.; Agnihotri, G. Chloramine-T-mediated chemoselective hydrolysis of thioglycosides into glycosyl hemiacetals under neutral conditions. Carbohydr. Res. 2004, 339, 885-890. (Pubitemid 38230897)
    • (2004) Carbohydrate Research , vol.339 , Issue.4 , pp. 885-890
    • Misra, A.K.1    Agnihotri, G.2
  • 26
    • 34249812387 scopus 로고    scopus 로고
    • Mild and efficient hydrolysis of thioglycosides to glycosyl hemiacetals using N-iodosaccharin
    • Mandal, P.K.; Misra, A.K. Mild and efficient hydrolysis of thioglycosides to glycosyl hemiacetals using N-iodosaccharin. Synlett 2007, 1207-1210.
    • (2007) Synlett , pp. 1207-1210
    • Mandal, P.K.1    Misra, A.K.2
  • 28
    • 0030798036 scopus 로고    scopus 로고
    • Synthesis of 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose: Sugar moiety of antitumor antibiotic bleomycin
    • DOI 10.1016/S0040-4020(97)00360-8, PII S0040402097003608
    • Oshitari, T.; Shibasaki, M.; Yoshizawa, T.; Tomita, M.; Takao, K.; Kobayashi, S. Synthesis of 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L- gulopyranose: sugar moiety of antitumor antibiotic bleomycin. Tetrahedron 1997, 53, 10993-11006. (Pubitemid 27326831)
    • (1997) Tetrahedron , vol.53 , Issue.32 , pp. 10993-11006
    • Oshitari, T.1    Shibasaki, M.2    Yoshizawa, T.3    Tomita, M.4    Takao, K.-I.5    Kobayashi, S.6
  • 29
    • 0027054165 scopus 로고
    • Structures of the glycopeptidolipid antigens of serovars 25 and 26 of the Mycobacterium avium serocomplex, synthesis of allyl glycosides of the outer disaccharide units and serology of the derived neoglycoproteins
    • DOI 10.1016/S0008-6215(92)84233-I
    • Aspinall, G.O.; Gammon, D.W.; Sood, R.K.; Chatterjee, D.; Rivoire, B.; Brennan, P.J. Structures of the glycopeptidolipid antigens of serovars 25 and 26 of the Mycobacterium avium serocomplex, synthesis of allyl glycosides of the outer disaccharide units and serology of the derived neoglycoproteins. Carbohydr. Res. 1992, 237, 57-77; (Pubitemid 23021095)
    • (1992) Carbohydrate Research , vol.237 , pp. 57-77
    • Aspinall, G.O.1    Gammon, D.W.2    Sood, R.K.3    Chatterjee, D.4    Rivoire, B.5    Brennan, P.J.6
  • 30
    • 0031669561 scopus 로고    scopus 로고
    • Synthesis of octopus glycosides: Core molecules for the construction of glycoclusters and carbohydrate-centered dendrimers
    • DOI 10.1016/S0008-6215(98)00155-4, PII S0008621598001554
    • Dubber, M.; Lindhorst, T.K. Synthesis of octopus glycosides: core molecules for the construction of glycoclusters and carbohydrate-centered dendrimers. Carbohydr. Res. 1998, 310, 35-41; (Pubitemid 28446185)
    • (1998) Carbohydrate Research , vol.310 , Issue.1-2 , pp. 35-41
    • Dubber, M.1    Lindhorst, T.K.2
  • 31
    • 0028762189 scopus 로고
    • Synthesis of allyl 3-deoxy- and 4-deoxy-β-Dgalactopyranoside and simultaneous preparation of Gal(1→2)- and Gal(1→3)-linked disaccharide glycosides
    • Lee, R.T.; Lee, Y.C. Synthesis of allyl 3-deoxy- and 4-deoxy-β- Dgalactopyranoside and simultaneous preparation of Gal(1→2)- and Gal(1→3)-linked disaccharide glycosides. Carbohydr. Res. 1994, 251, 69-79;
    • (1994) Carbohydr. Res. , vol.251 , pp. 69-79
    • Lee, R.T.1    Lee, Y.C.2
  • 32
    • 0035826708 scopus 로고    scopus 로고
    • A Facile and Effective Synthesis of α-(1→6)-linked Mannose Di-, Tri-, Tetra-, Hexa-, Octa-, and Do-decasaccharides, and β-(1→6)-linked Glucose Di-, Tri-, Tetra-, Hexa-, and Octasaccharides Using Sugar Trichloroacetimidates As the Donors and Unprotected or Partially Protected Glycosides As the Acceptors
    • Zhu, Y.; Kong, F. A facile and effective synthesis of α-(1→6)-linked mannose di-, tri-, tetra-, hexa-, octa-, and do-decasaccharides, and β-(1→6)-linked glucose di-, tri-, tetra-, hexa-, and octasaccharides using sugar trichloroacetimidates as the donors and unprotected or partially protected glycosides as the acceptors. Carbohydr. Res. 2001, 332, 1-21.
    • (2001) Carbohydr. Res. , vol.332 , pp. 1-21
    • Zhu, Y.1    Kong, F.2
  • 34
    • 28444435860 scopus 로고    scopus 로고
    • Syntheses of glucose-containing E5564 analogues and their LPS-antagonistic activities
    • DOI 10.1016/j.tet.2005.09.115, PII S0040402005017606
    • Shiozaki, M.; Doi, H.; Tanaka, D.; Shimozato, T.; Kurakata, S.-i. Syntheses of glucose-containing E5564 analogues and their LPS-antagonistic activities. Tetrahedron 2006, 62, 205-225; (Pubitemid 41740978)
    • (2006) Tetrahedron , vol.62 , Issue.1 , pp. 205-225
    • Shiozaki, M.1    Doi, H.2    Tanaka, D.3    Shimozato, T.4    Kurakata, S.-I.5
  • 35
    • 0037152578 scopus 로고    scopus 로고
    • Total synthesis of sphingofungin E from D-glucose derivative
    • DOI 10.1016/S0040-4020(02)01058-X, PII S004040200201058X
    • Nakamura, T.; Shiozaki, M. Total synthesis of sphingofungin E from D-glucose derivative. Tetrahedron 2002, 58, 8779-8791; (Pubitemid 35284574)
    • (2002) Tetrahedron , vol.58 , Issue.43 , pp. 8779-8791
    • Nakamura, T.1    Shiozaki, M.2
  • 36
    • 0035795006 scopus 로고    scopus 로고
    • Total synthesis of sphingofungin E
    • DOI 10.1016/S0040-4039(01)00246-5, PII S0040403901002465
    • Nakamura, T.; Shiozaki, M. Total synthesis of sphingofungin E. Tetrahedron Lett. 2001, 42, 2701-2704. (Pubitemid 32245534)
    • (2001) Tetrahedron Letters , vol.42 , Issue.14 , pp. 2701-2704
    • Nakamura, T.1    Shiozaki, M.2
  • 38
    • 0003090172 scopus 로고    scopus 로고
    • A novel and efficient deprotection of the allyl group at the anomeric oxygen of carbohydrates
    • Yu, B.; Zhang, J.; Lu, S.; Hui, Y. A novel and efficient deprotection of the allyl group at the anomeric oxygen of carbohydrates. Synlett 1998, 29-30. (Pubitemid 128693869)
    • (1998) Synlett , Issue.1 , pp. 29-30
    • Yu, B.1    Zhang, J.2    Lu, S.3    Hui, Y.4
  • 39
    • 0026669108 scopus 로고
    • A useful method for deprotection of the protective allyl group at the anomeric oxygen of carbohydrate moieties using tetrakis(triphenylphosphine) palladium
    • Nakayama, K.; Uoto, K.; Higashi, K.; Soga, T.; Kusama, T. A useful method for deprotection of the protective allyl group at the anomeric oxygen of carbohydrate moieties using tetrakis(triphenylphosphine) palladium. Chem. Pharm. Bull. 1992, 40, 1718-1720;
    • (1992) Chem. Pharm. Bull. , vol.40 , pp. 1718-1720
    • Nakayama, K.1    Uoto, K.2    Higashi, K.3    Soga, T.4    Kusama, T.5
  • 40
    • 0027291265 scopus 로고
    • A new method for the cleavage of allyl glycosides
    • DOI 10.1016/S0040-4039(00)73801-9
    • Lüning, J.; Möller, U.; Debski, N.; Welzel, P. A new method for the cleavage of allyl glycosides. Tetrahedron Lett. 1993, 34, 5871-5874. (Pubitemid 23282114)
    • (1993) Tetrahedron Letters , vol.34 , Issue.37 , pp. 5871-5874
    • Luning, J.1    Moller, U.2    Debski, N.3    Welzel, P.4
  • 41
    • 69249162204 scopus 로고    scopus 로고
    • Total synthesis of the heptasaccharide repeating unit of the iron-binding exopolysaccharide secreted by Klebsiella oxytoca BAS-10
    • Guchhait, G.; Misra, A.K. Total synthesis of the heptasaccharide repeating unit of the iron-binding exopolysaccharide secreted by Klebsiella oxytoca BAS-10. Tetrahedron Asymm. 2009, 20, 1791-1797;
    • (2009) Tetrahedron Asymm , vol.20 , pp. 1791-1797
    • Guchhait, G.1    Misra, A.K.2
  • 42
    • 69849091829 scopus 로고    scopus 로고
    • Synthesis of a trisaccharide and a tetrasaccharide from the cell-wall lipopolysaccharides of Azospirillum brasilense S17
    • Pandey S.,Ghosh S.,Misra A.K. Synthesis of a trisaccharide and a tetrasaccharide from the cell-wall lipopolysaccharides of Azospirillum brasilense S17. Synthesis 2009, 2584-2590
    • (2009) Synthesis , pp. 2584-2590
    • Pandey, S.1    Ghosh, S.2    Misra, A.K.3
  • 43
    • 67749120488 scopus 로고    scopus 로고
    • First synthesis of a pentasaccharide repeating unit of the O-antigenic polysaccha-ride from enterohaemorrhagic Escherichia coli O48: H21
    • Panchadhayee, R.; Misra, A.K. First synthesis of a pentasaccharide repeating unit of the O-antigenic polysaccha-ride from enterohaemorrhagic Escherichia coli O48:H21. Tetrahedron Asymm. 2009, 20, 1550-1555;
    • (2009) Tetrahedron Asymm , vol.20 , pp. 1550-1555
    • Panchadhayee, R.1    Misra, A.K.2
  • 44
    • 63449118662 scopus 로고    scopus 로고
    • Total synthesis of a unique tetrasaccharide present in the human clotting factor IX and mammalian Notch 1 receptor
    • Mukherjee, C.; Misra, A.K. Total synthesis of a unique tetrasaccharide present in the human clotting factor IX and mammalian Notch 1 receptor.Tetrahedron Asymm. 2009, 20, 473-477;
    • (2009) Tetrahedron Asymm , vol.20 , pp. 473-477
    • Mukherjee, C.1    Misra, A.K.2
  • 45
    • 58349090837 scopus 로고    scopus 로고
    • Synthesis of a unique trisac-charide having an acetal linkage between open-chain and cyclic sugar found in the cell wall of Proteus
    • Mukherjee, C.; Misra, A.K. Synthesis of a unique trisac-charide having an acetal linkage between open-chain and cyclic sugar found in the cell wall of Proteus. Tetrahedron Asymm. 2008, 19, 2746-2751.
    • (2008) Tetrahedron Asymm , vol.19 , pp. 2746-2751
    • Mukherjee, C.1    Misra, A.K.2


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