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Volumn 21, Issue 6, 2002, Pages 453-470

Synthesis of 2-(trimethylsilyl)ethyl α-D-mannopyranosides revisited

Author keywords

2 (Trimethylsilyl)ethyl glycosides; Anomerization; Glycosylation; NIS AgOTf

Indexed keywords

ACETIC ACID DERIVATIVE; PYRANOSIDE; SILVER DERIVATIVE; SUCCINIMIDE DERIVATIVE;

EID: 0036925440     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-120016846     Document Type: Article
Times cited : (9)

References (21)
  • 1
    • 33845278486 scopus 로고
    • 2-(Trimethylsilyl)ethyl glycosides. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars
    • Jansson, K.; Ahlfors, S.; Frejd, T.; Kihlberg, J.; Magnusson, G.; Dahmen, J.; Noori, G.; Stenwall, K. 2-(Trimethylsilyl)ethyl glycosides. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars. J. Org. Chem. 1988, 53, 5629-5647.
    • (1988) J. Org. Chem. , vol.53 , pp. 5629-5647
    • Jansson, K.1    Ahlfors, S.2    Frejd, T.3    Kihlberg, J.4    Magnusson, G.5    Dahmen, J.6    Noori, G.7    Stenwall, K.8
  • 2
    • 0012237203 scopus 로고
    • 2-(Trimethylsilylethyl) glycosides. Treatment with electrophilic reagents to give trimethylsilyl and methoxymethyl glucopyranosides and glucopyranosyl chlorides
    • Jansson, K.; Magnusson, G. 2-(Trimethylsilylethyl) glycosides. Treatment with electrophilic reagents to give trimethylsilyl and methoxymethyl glucopyranosides and glucopyranosyl chlorides. Tetrahedron 1990, 46, 59-64.
    • (1990) Tetrahedron , vol.46 , pp. 59-64
    • Jansson, K.1    Magnusson, G.2
  • 3
    • 0025277564 scopus 로고
    • 2-(Trimethylsilyl)ethyl glycosides. Transformation into glycopyranosyl chlorides
    • Jansson, K.; Noori, G.; Magnusson, G. 2-(Trimethylsilyl)ethyl glycosides. Transformation into glycopyranosyl chlorides. J. Org. Chem. 1990, 55, 3181-3185.
    • (1990) J. Org. Chem. , vol.55 , pp. 3181-3185
    • Jansson, K.1    Noori, G.2    Magnusson, G.3
  • 4
    • 0025358881 scopus 로고
    • A facile, one-step procedure for the conversion of 2-(trimethylsilyl)ethyl glycosides to their glycosyl chlorides
    • Kartha, K.P.R.; Jennings, H.J. A facile, one-step procedure for the conversion of 2-(trimethylsilyl)ethyl glycosides to their glycosyl chlorides. Tetrahedron Lett. 1990, 31, 2537-2540.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2537-2540
    • Kartha, K.P.R.1    Jennings, H.J.2
  • 5
    • 0027366313 scopus 로고
    • A synthesis of 2-(trimethylsilyl)ethyl α-D-mannopyranoside
    • Pozsgay, V. A synthesis of 2-(trimethylsilyl)ethyl α-D-mannopyranoside. Tetrahedron Lett. 1993, 34, 7175-7178.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7175-7178
    • Pozsgay, V.1
  • 6
    • 0029947743 scopus 로고    scopus 로고
    • Synthesis of ligands related to the Vibrio cholerae O-specific antigen. Part 11. Synthesis of four glycosides of a disaccharide fragment representing the terminus of the O-polysaccharide of Vibrio cholerae O:1, serotype Inaba, bearing aglycons suitable for linking to proteins
    • Ogawa, Y.; Lei, P.-S.; Kováč, P. Synthesis of ligands related to the Vibrio cholerae O-specific antigen. Part 11. Synthesis of four glycosides of a disaccharide fragment representing the terminus of the O-polysaccharide of Vibrio cholerae O:1, serotype Inaba, bearing aglycons suitable for linking to proteins. Carbohydr. Res. 1996, 288, 85-98.
    • (1996) Carbohydr. Res. , vol.288 , pp. 85-98
    • Ogawa, Y.1    Lei, P.-S.2    Kováč, P.3
  • 7
    • 0030608338 scopus 로고    scopus 로고
    • Synthesis of ligands related to the Vibrio cholerae O-specific antigen. Part 12. Synthesis of eight glycosides of hexasaccharide fragments representing the terminus of the O-polysaccharide of Vibrio cholerae O:1, serotype Inaba and Ogawa, bearing aglycons suitable for linking to proteins
    • Ogawa, Y.; Lei, P.-S.; Kováč, P. Synthesis of ligands related to the Vibrio cholerae O-specific antigen. Part 12. Synthesis of eight glycosides of hexasaccharide fragments representing the terminus of the O-polysaccharide of Vibrio cholerae O:1, serotype Inaba and Ogawa, bearing aglycons suitable for linking to proteins. Carbohydr. Res. 1996, 293, 173-194.
    • (1996) Carbohydr. Res. , vol.293 , pp. 173-194
    • Ogawa, Y.1    Lei, P.-S.2    Kováč, P.3
  • 8
    • 0028582222 scopus 로고
    • Orthogonal glycosylation strategy in oligosaccharide synthesis
    • Kanie, O.; Ito, Y.; Ogawa, T. Orthogonal glycosylation strategy in oligosaccharide synthesis. J. Am. Chem. Soc. 1994, 116, 12073-12074.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 12073-12074
    • Kanie, O.1    Ito, Y.2    Ogawa, T.3
  • 9
    • 0025309559 scopus 로고
    • Iodonium promoted reactions of disarmed thioglycosides
    • Konradson, P.; Udodong, U.E.; Fraser-Reid, B. Iodonium promoted reactions of disarmed thioglycosides. Tetrahedron Lett. 1990, 31, 4313-4316.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 4313-4316
    • Konradson, P.1    Udodong, U.E.2    Fraser-Reid, B.3
  • 10
    • 0002503127 scopus 로고    scopus 로고
    • Glycosylation properties and reactivity of thioglycosides, sulfoxides and other S-glycosides: Current scope and future prospects
    • Khan, S.H., O'Neill, R.A., Eds.; Harwood Academic Publishers: Amsterdam
    • Norberg, T. Glycosylation properties and reactivity of thioglycosides, sulfoxides and other S-glycosides: Current scope and future prospects. In Modern Methods in Carbohydrate Synthesis; Khan, S.H., O'Neill, R.A., Eds.; Harwood Academic Publishers: Amsterdam, 1996; 82-106.
    • (1996) Modern Methods in Carbohydrate Synthesis , pp. 82-106
    • Norberg, T.1
  • 11
    • 0012335701 scopus 로고    scopus 로고
    • Synthesis of tri- and tetrasaccharide derivatives related to Klebsiella type 57
    • Sarbajna, S.; Roy, N. Synthesis of tri- and tetrasaccharide derivatives related to Klebsiella type 57. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1998, 37B (3), 252-256.
    • (1998) Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. , vol.37 B , Issue.3 , pp. 252-256
    • Sarbajna, S.1    Roy, N.2
  • 12
    • 33947446783 scopus 로고
    • Ethyl thioglycosides of D-mannose and D-galactose and a new synthesis of styracitol
    • Fried, J.; Walz, D.E. Ethyl thioglycosides of D-mannose and D-galactose and a new synthesis of styracitol. J. Am. Chem. Soc. 1949, 71, 140-143.
    • (1949) J. Am. Chem. Soc. , vol.71 , pp. 140-143
    • Fried, J.1    Walz, D.E.2
  • 13
    • 84981422033 scopus 로고
    • Synthesis of glycosides using 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide
    • Kunz, H.; Harreus, A. Synthesis of glycosides using 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide. Liebigs Ann. Chem. 1982, 41-48.
    • (1982) Liebigs Ann. Chem. , pp. 41-48
    • Kunz, H.1    Harreus, A.2
  • 14
    • 4244144203 scopus 로고
    • A study of 13CH coupling constants in hexopyranoses
    • Bock, K.; Pedersen, C. A study of 13CH coupling constants in hexopyranoses. J. Chem. Soc., Perkin Trans. 2 1974, 293-297.
    • (1974) J. Chem. Soc., Perkin Trans. 2 , pp. 293-297
    • Bock, K.1    Pedersen, C.2
  • 15
    • 0030448244 scopus 로고    scopus 로고
    • An improved method for the preparation of some ethyl 1-thioglycosides
    • Das, S.K.; Roy, N. An improved method for the preparation of some ethyl 1-thioglycosides. Carbohydr. Res. 1996, 296, 275-277.
    • (1996) Carbohydr. Res. , vol.296 , pp. 275-277
    • Das, S.K.1    Roy, N.2
  • 16
    • 0026729007 scopus 로고
    • Synthesis and conformational and NMR studies of α-D-mannopyranosyl- and α-D-mannopyranosyl-(1-2)-α-D-mannopyranosyl linked to L-serine and L-threonine
    • Helander, A.; Kenne, L.; Oscarson, S.; Peters, T.; Brisson, J.-R. Synthesis and conformational and NMR studies of α-D-mannopyranosyl- and α-D-mannopyranosyl-(1-2)-α-D-mannopyranosyl linked to L-serine and L-threonine. Carbohydr. Res. 1992, 230, 299-318.
    • (1992) Carbohydr. Res. , vol.230 , pp. 299-318
    • Helander, A.1    Kenne, L.2    Oscarson, S.3    Peters, T.4    Brisson, J.-R.5
  • 18
    • 0027086437 scopus 로고
    • Glycosylation using a one-electron-transfer, homogeneous reagent. Application to an efficient synthesis of the trimannosyl core of N-glycosylproteins
    • Zhang, Y.-M.; Mallet, J.-M.; Sinaÿ, P. Glycosylation using a one-electron-transfer, homogeneous reagent. Application to an efficient synthesis of the trimannosyl core of N-glycosylproteins. Carbohydr. Res. 1992, 236, 73-88.
    • (1992) Carbohydr. Res. , vol.236 , pp. 73-88
    • Zhang, Y.-M.1    Mallet, J.-M.2    Sinaÿ, P.3
  • 19
    • 0000335136 scopus 로고
    • The synthesis of β-mannopyranosides by intramolecular aglycon delivery: Scope and limitation of the existing methodology
    • Barresi, F.; Hindsgaul, O. The synthesis of β-mannopyranosides by intramolecular aglycon delivery: Scope and limitation of the existing methodology. Can. J. Chem. 1994, 72, 1447-1465.
    • (1994) Can. J. Chem. , vol.72 , pp. 1447-1465
    • Barresi, F.1    Hindsgaul, O.2
  • 20
    • 0000611325 scopus 로고
    • Synthetic antigenic determinants of the Brucella A polysaccharide: A disaccharide thioglycoside for block synthesis of pentasaccharide and lower homologues of a 1,2-linked 4,6-dideoxy-4-formamido-α-D-mannose
    • Peters, T.; Bundle, D.R. Synthetic antigenic determinants of the Brucella A polysaccharide: A disaccharide thioglycoside for block synthesis of pentasaccharide and lower homologues of a 1,2-linked 4,6-dideoxy-4-formamido-α-D-mannose. Can. J. Chem. 1989, 67, 491-496.
    • (1989) Can. J. Chem. , vol.67 , pp. 491-496
    • Peters, T.1    Bundle, D.R.2
  • 21
    • 0033450727 scopus 로고    scopus 로고
    • An alternative method for regioselective, anomeric deacylation
    • Zhang, J.; Kováč, P. An alternative method for regioselective, anomeric deacylation. J. Carbohydr. Chem. 1999, 18, 461-469.
    • (1999) J. Carbohydr. Chem. , vol.18 , pp. 461-469
    • Zhang, J.1    Kováč, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.