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Volumn 37, Issue 5, 2007, Pages 691-701

Amberlyst 15-catalyzed efficient synthesis of 2,3-unsaturated glycosides via Ferrier rearrangement for glycal

Author keywords

2,3 unsaturated glycoside; Amberlyst 15; Ferrier rearrangement; Glycal; Glycosidation

Indexed keywords

ACID; ALLYL O (4',6' DI O ACETYL 2',3' DIDEOXY ALPHA DEXTRO ERYTHRO HEX 2' ENOPYRANOSYL)(1-6) 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; AMBERLYST 15; BENZYL N (BENZYLOXYCARBONYL)THREONINE 4,6 DI O ACETYL 2,3 DIDEOXY ALPHA DEXTRO ERYTHRO HEX 2 ENOPYRANOSIDE; GLUCONATE CALCIUM; GLUCOSIDE; METHYL O (4',6' DI O ACETYL 2',3' DIDEOXY ALPHA DEXTRO ERYTHRO HEX 2' ENOPYRANOSYL)(1-3) 2 O BENZOYL 4,6 O BENZYLIDENE ALPHA DEXTRO GLUCOPYRANOSIDE; UNCLASSIFIED DRUG;

EID: 33847104634     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910601131353     Document Type: Article
Times cited : (15)

References (33)
  • 1
    • 0006881877 scopus 로고
    • Some progeny of 2,3-unsaturated sugars - they little resemble grandfather glucose: Ten years later
    • (a) Fraser-Reid, B. Some progeny of 2,3-unsaturated sugars - they little resemble grandfather glucose: Ten years later. Acc. Chem. Res. 1985, 18, 347-354.;
    • (1985) Acc. Chem. Res , vol.18 , pp. 347-354
    • Fraser-Reid, B.1
  • 2
    • 33847123910 scopus 로고    scopus 로고
    • Some progeny of 2,3-unsaturated sugars - they little resemble grandfather glucose: Twenty years later. Acc. Chem. Res. 1996, 29, 57-66.;
    • (b) Some progeny of 2,3-unsaturated sugars - they little resemble grandfather glucose: Twenty years later. Acc. Chem. Res. 1996, 29, 57-66.;
  • 3
    • 0035806012 scopus 로고    scopus 로고
    • Synthesis and hypolipidemic activity of N-phthalimidomethyl tetra-O-acyl-α-D- mannopyranosides
    • (c) Srivastava, R. M.; Oliveira, F. J. S.; Silva, L. P.; de Freitas Filho, J. R.; Lima, V. L. M. Synthesis and hypolipidemic activity of N-phthalimidomethyl tetra-O-acyl-α-D- mannopyranosides. Carbohydr. Res. 2001, 332, 335-340.
    • (2001) Carbohydr. Res , vol.332 , pp. 335-340
    • Srivastava, R.M.1    Oliveira, F.J.S.2    Silva, L.P.3    de Freitas Filho, J.R.4    Lima, V.L.M.5
  • 5
    • 33845554821 scopus 로고
    • The chemistry of hexenuloses
    • (b) Holder, N. The chemistry of hexenuloses. Chem. Rev. 1982, 82, 287-332.
    • (1982) Chem. Rev , vol.82 , pp. 287-332
    • Holder, N.1
  • 6
    • 0000645983 scopus 로고    scopus 로고
    • Substitution-with-allylic-rearrangement reactions of glycal derivatives
    • Ferrier, R. J. Substitution-with-allylic-rearrangement reactions of glycal derivatives. Top. Curr. Chem. 2001, 215, 153-175.
    • (2001) Top. Curr. Chem , vol.215 , pp. 153-175
    • Ferrier, R.J.1
  • 7
    • 37049119941 scopus 로고    scopus 로고
    • Ferrier, R. J.; Prasad, N. J. Unsaturated carbohydrates, IX: Synthesis of 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides from tri-O-acetyl-D-glucal. J. Chem. Soc. C 1969, 570-574.
    • Ferrier, R. J.; Prasad, N. J. Unsaturated carbohydrates, IX: Synthesis of 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides from tri-O-acetyl-D-glucal. J. Chem. Soc. C 1969, 570-574.
  • 8
    • 0034685292 scopus 로고    scopus 로고
    • Indium trichloride catalyzed glycosidation: An expeditious synthesis of 2,3-unsaturated glycopyranosides
    • (a) Babu, B. S.; Balasubramanian, K. K. Indium trichloride catalyzed glycosidation: An expeditious synthesis of 2,3-unsaturated glycopyranosides. Tetrahedron Lett. 2000, 41, 1271-1274;
    • (2000) Tetrahedron Lett , vol.41 , pp. 1271-1274
    • Babu, B.S.1    Balasubramanian, K.K.2
  • 9
    • 0042412071 scopus 로고    scopus 로고
    • 3-catalyzed Ferrier rearrangement of acetylglycals: Synthesis of 2,3-unsturated glycopyranosides
    • 3-catalyzed Ferrier rearrangement of acetylglycals: Synthesis of 2,3-unsturated glycopyranosides. Synlett 2003, 1607-1610.
    • (2003) Synlett , pp. 1607-1610
    • Das, S.K.1    Reddy, K.A.2    Roy, J.3
  • 10
    • 0002896307 scopus 로고
    • Synthesis of alkyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2- enopyranosides from 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D- lyxo-hex-1-enitol (3,4,6-tri-O-acetyl-D-galactal)
    • Grynkiewicz, G.; Priebe, W.; Zamojski, A. Synthesis of alkyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2- enopyranosides from 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D- lyxo-hex-1-enitol (3,4,6-tri-O-acetyl-D-galactal). Carbohydr. Res. 1979, 68, 33-41.
    • (1979) Carbohydr. Res , vol.68 , pp. 33-41
    • Grynkiewicz, G.1    Priebe, W.2    Zamojski, A.3
  • 12
    • 0033815016 scopus 로고    scopus 로고
    • Scandium triflate catalyzed Ferrier rearrangement: An efficient synthesis of 2,3-unsaturated glycopyranosides
    • Yadav, J. S.; Subba Reddy, B. V.; Murthy, C. V. S. R.; Kumar, G. M. Scandium triflate catalyzed Ferrier rearrangement: An efficient synthesis of 2,3-unsaturated glycopyranosides. Synlett 2000, 1450-1451.
    • (2000) Synlett , pp. 1450-1451
    • Yadav, J.S.1    Subba Reddy, B.V.2    Murthy, C.V.S.R.3    Kumar, G.M.4
  • 13
    • 0033795218 scopus 로고    scopus 로고
    • Ferric chloride: A new and very efficient catalyst for the Ferrier glycosylation reaction
    • (a) Masson, C.; Soto, J.; Bessodes, M. Ferric chloride: A new and very efficient catalyst for the Ferrier glycosylation reaction. Synlett 2000, 1281-1282;
    • (2000) Synlett , pp. 1281-1282
    • Masson, C.1    Soto, J.2    Bessodes, M.3
  • 15
    • 0036222957 scopus 로고    scopus 로고
    • An efficient method for the synthesis of 2,3-unsaturated glycopyranosides catalyzed by bismuth trichloride in Ferrier rearrangement
    • Swamy, N. R.; Venkateswarlu, Y. An efficient method for the synthesis of 2,3-unsaturated glycopyranosides catalyzed by bismuth trichloride in Ferrier rearrangement. Synthesis 2002, 598-600.
    • (2002) Synthesis , pp. 598-600
    • Swamy, N.R.1    Venkateswarlu, Y.2
  • 16
    • 0042882780 scopus 로고    scopus 로고
    • 2-catalyzed Ferrier reaction; Synthesis of 2,3-unsaturated 1-O-glucopyranosides of allylic, benzylic and tertiary alcohols
    • 2-catalyzed Ferrier reaction; Synthesis of 2,3-unsaturated 1-O-glucopyranosides of allylic, benzylic and tertiary alcohols. Tetrahedron Lett. 2003, 44, 7257-7259.
    • (2003) Tetrahedron Lett , vol.44 , pp. 7257-7259
    • Bettadaiah, B.K.1    Srinivas, P.2
  • 17
    • 0033618317 scopus 로고    scopus 로고
    • Synthesis of 2,3-unsaturated thioglycopyranosides mediated by lithium tetrafluoroborate
    • Babu, B. S.; Balasubramnaian, K. K. Synthesis of 2,3-unsaturated thioglycopyranosides mediated by lithium tetrafluoroborate. Tetrahedron Lett. 1999, 40, 5777-5778.
    • (1999) Tetrahedron Lett , vol.40 , pp. 5777-5778
    • Babu, B.S.1    Balasubramnaian, K.K.2
  • 18
    • 14844330112 scopus 로고
    • Practical glycosidation method of glycals using montmorillonite K-10 as an environmentally acceptable and inexpensive industrial catalyst
    • (a) Toshima, K.; Ishizuka, T.;Matsuo, G.;Nakata, M. Practical glycosidation method of glycals using montmorillonite K-10 as an environmentally acceptable and inexpensive industrial catalyst. Synlett 1995, 306-308;
    • (1995) Synlett , pp. 306-308
    • Toshima, K.1    Ishizuka, T.2    Matsuo, G.3    Nakata, M.4
  • 19
    • 0037119676 scopus 로고    scopus 로고
    • Microwave-induced, Montmorillonite K-10-catalyzed Ferrier rearrangement of tri-O-acetyl-D-galactal: Mild, eco-friendly, rapid glycosidation with allylic rearrangement
    • (b) Shanmugasundaram, B.; Bose, A. K.; Balasubramanian, K. K. Microwave-induced, Montmorillonite K-10-catalyzed Ferrier rearrangement of tri-O-acetyl-D-galactal: Mild, eco-friendly, rapid glycosidation with allylic rearrangement. Tetrahedron Lett. 2002, 43, 6795-6798;
    • (2002) Tetrahedron Lett , vol.43 , pp. 6795-6798
    • Shanmugasundaram, B.1    Bose, A.K.2    Balasubramanian, K.K.3
  • 20
    • 0037128473 scopus 로고    scopus 로고
    • Microwave-induced synthesis of 2,3-unsaturated O-glycosides under solvent-free conditions
    • (c) de Oliveira, R. N.; de Freitas, J. R.; Srivastava, R. M. Microwave-induced synthesis of 2,3-unsaturated O-glycosides under solvent-free conditions. Tetrahedron Lett. 2002, 43, 2141-2143.
    • (2002) Tetrahedron Lett , vol.43 , pp. 2141-2143
    • de Oliveira, R.N.1    de Freitas, J.R.2    Srivastava, R.M.3
  • 21
    • 0036431738 scopus 로고    scopus 로고
    • 3 immobilized in ionic liquids: A novel and recyclable reaction media for the synthesis of 2,3-unsaturated glycopyranosides
    • 3 immobilized in ionic liquids: A novel and recyclable reaction media for the synthesis of 2,3-unsaturated glycopyranosides. J. Chem. Soc., Perkin Trans. 1 2002, 2390-2394.
    • (2002) J. Chem. Soc., Perkin Trans. 1 , pp. 2390-2394
    • Yadav, J.S.1    Reddy, B.V.S.2    Reddy, J.S.S.3
  • 22
    • 2342483630 scopus 로고    scopus 로고
    • 4-catalyzed efficient Ferrier glycosylation: A facile synthesis of pseudoglycals
    • 4-catalyzed efficient Ferrier glycosylation: A facile synthesis of pseudoglycals. Synthesis 2004, 834-836;
    • (2004) Synthesis , pp. 834-836
    • Smitha, G.1    Reddy, C.S.2
  • 23
    • 33746287518 scopus 로고    scopus 로고
    • Zirconium (IV) chloride catalyzed synthesis of 2,3-unsaturated C, N, O, S, and heteroaromatic glycosylation in the ferrier rearrangement
    • (b) Swamy, N. R.; Srinivasulu, M.; Reddy, T. S.; Goud, T. V.; Venkateswarlu, Y. Zirconium (IV) chloride catalyzed synthesis of 2,3-unsaturated C, N, O, S, and heteroaromatic glycosylation in the ferrier rearrangement. J. Carbohydr. Chem. 2004, 23, 435-441.
    • (2004) J. Carbohydr. Chem , vol.23 , pp. 435-441
    • Swamy, N.R.1    Srinivasulu, M.2    Reddy, T.S.3    Goud, T.V.4    Venkateswarlu, Y.5
  • 24
    • 1042288189 scopus 로고    scopus 로고
    • Stereoselective palladium-catalyzed O-glycosylation using glycals
    • Kim, H.; Men, H. B.; Lee, C. Stereoselective palladium-catalyzed O-glycosylation using glycals. J. Am. Chem. Soc. 2004, 126, 1336-1337.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 1336-1337
    • Kim, H.1    Men, H.B.2    Lee, C.3
  • 25
    • 2942585504 scopus 로고    scopus 로고
    • A mild, efficient and α-selective glycosidation by using potassium dodecatungstocobaltate trihydrate as catalyst
    • Rafiee, E.; Tangestaninejad, S.; Habibi, M. H.; Mirkhani, V. A mild, efficient and α-selective glycosidation by using potassium dodecatungstocobaltate trihydrate as catalyst. Bioorg. Med. Chem. Lett. 2004, 14, 3611-3614.
    • (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 3611-3614
    • Rafiee, E.1    Tangestaninejad, S.2    Habibi, M.H.3    Mirkhani, V.4
  • 26
    • 4344701510 scopus 로고    scopus 로고
    • 4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O- glucosides and a chiral furan diol from 2,3-glycals
    • 4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O- glucosides and a chiral furan diol from 2,3-glycals. J. Org. Chem. 2004, 69, 6137-6140;
    • (2004) J. Org. Chem , vol.69 , pp. 6137-6140
    • Agarwal, A.1    Rani, S.2    Vankar, Y.D.3
  • 28
    • 37049085215 scopus 로고
    • Glycosidation of glycals by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as a catalytic promoter
    • Toshima, K.; Ishizuka, T.; Matsuo, G.; Nakata, M.; Konoshita, M. Glycosidation of glycals by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as a catalytic promoter. J. Chem. Soc., Chem. Commun. 1993, 704-706.
    • (1993) J. Chem. Soc., Chem. Commun , pp. 704-706
    • Toshima, K.1    Ishizuka, T.2    Matsuo, G.3    Nakata, M.4    Konoshita, M.5
  • 29
    • 0035798050 scopus 로고    scopus 로고
    • Ceric ammonium nitrate-catalyzed tetrahydropyranylation of alcohols and synthesis of 2-deoxy-O-glycosides
    • Pachamuthu, K.; Vankar, Y. D. Ceric ammonium nitrate-catalyzed tetrahydropyranylation of alcohols and synthesis of 2-deoxy-O-glycosides. J. Org. Chem. 2001, 66, 7511-7513.
    • (2001) J. Org. Chem , vol.66 , pp. 7511-7513
    • Pachamuthu, K.1    Vankar, Y.D.2
  • 30
    • 0010689758 scopus 로고    scopus 로고
    • Gutmann, H. R.; Chang, S. F. DL- and L-threonine p-toluenesulfonate benzyl ester. J. Org. Chem. 1962, 27, 2248-2250.
    • Gutmann, H. R.; Chang, S. F. DL- and L-threonine p-toluenesulfonate benzyl ester. J. Org. Chem. 1962, 27, 2248-2250.
  • 31
    • 0028787280 scopus 로고
    • Easy synthesis and different conformational behavior of purine and pyrimidine: β-D- Glycero-pent-2′-enopyranosyl nucleosides
    • (a) Doboszewski, B.; Blaton, N.; Herdewijn, P. Easy synthesis and different conformational behavior of purine and pyrimidine: β-D- Glycero-pent-2′-enopyranosyl nucleosides. J. Org. Chem. 1995, 60, 7909-7919;
    • (1995) J. Org. Chem , vol.60 , pp. 7909-7919
    • Doboszewski, B.1    Blaton, N.2    Herdewijn, P.3
  • 32
    • 0000667781 scopus 로고
    • De novo synthesis of carbohydrates and related natural products, part 6: Synthesis and glycosidation reactions of acetylated racemic pseudoglycals
    • (b) Schmidt, R. R.; Angerbauer, R. De novo synthesis of carbohydrates and related natural products, part 6: Synthesis and glycosidation reactions of acetylated racemic pseudoglycals. Carbohydr. Res. 1981, 89, 193-201.
    • (1981) Carbohydr. Res , vol.89 , pp. 193-201
    • Schmidt, R.R.1    Angerbauer, R.2
  • 33
    • 0000316365 scopus 로고    scopus 로고
    • 2, is known to catalyze glycals with alcohols to form the 2-deoxy-O-glycosides, See Sabesan, S.; Neira, S. Synthesis of 2-deoxy sugars from glycols. J. Org. Chem. 1991, 56, 5468-5472.
    • 2, is known to catalyze glycals with alcohols to form the 2-deoxy-O-glycosides, See Sabesan, S.; Neira, S. Synthesis of 2-deoxy sugars from glycols. J. Org. Chem. 1991, 56, 5468-5472.


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