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Volumn 23, Issue 2-3, 2004, Pages 83-93

Synthesis of C-3 branched allyl and pentadienyl glucosamines via radical coupling of sugar-thionocarbonates

Author keywords

Allyltributyltin; C Branched alkenyl sugars; Pentadienyltributyltin; Radical reaction; Thionocarbonates

Indexed keywords


EID: 33746671835     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1081/CAR-120030469     Document Type: Article
Times cited : (6)

References (25)
  • 1
    • 0032552046 scopus 로고    scopus 로고
    • Recent advances in stereoselective C-glycoside synthesis
    • Du, Y.; Linhardt, R.J.; Vlahov, I.R. Recent advances in stereoselective C-glycoside synthesis. Tetrahedron 1998, 54, 9913-9959.
    • (1998) Tetrahedron , vol.54 , pp. 9913-9959
    • Du, Y.1    Linhardt, R.J.2    Vlahov, I.R.3
  • 2
    • 0000733916 scopus 로고    scopus 로고
    • C-glycosidation technology with free radical reactions
    • Togo, H.; He, W.; Waki, Y.; Yokoyama, M. C-glycosidation technology with free radical reactions. Synlett. 1998, 700-717.
    • (1998) Synlett , pp. 700-717
    • Togo, H.1    He, W.2    Waki, Y.3    Yokoyama, M.4
  • 5
    • 0002476212 scopus 로고    scopus 로고
    • Nucleophilic C-glycosyl donors for C-glycoside synthesis
    • Beau, J.-M.; Gallagher, T. Nucleophilic C-glycosyl donors for C-glycoside synthesis. Top. Curr. Chem. 1997, 187, 1-54.
    • (1997) Top. Curr. Chem. , vol.187 , pp. 1-54
    • Beau, J.-M.1    Gallagher, T.2
  • 6
    • 0000627598 scopus 로고    scopus 로고
    • C-glycosyl compounds as stable analogs of natural oligosaccharides and glycosyl aminoacids, in glycoscience
    • Fraser-Reid, B., Tatsuta, K., Thiem, J., Eds.; Springer Verlag: Heidelberg
    • Beau, J.-M.; Vauzeilles, B.; Skrydstrup, T. C-glycosyl compounds as stable analogs of natural oligosaccharides and glycosyl aminoacids, in glycoscience. In Chemistry and Chemical Biology; Fraser-Reid, B., Tatsuta, K., Thiem, J., Eds.; Springer Verlag: Heidelberg, 2001; Vol. 3, 2679-2724.
    • (2001) Chemistry and Chemical Biology , vol.3 , pp. 2679-2724
    • Beau, J.-M.1    Vauzeilles, B.2    Skrydstrup, T.3
  • 7
    • 0029860709 scopus 로고    scopus 로고
    • The synthesis of C-trisaccharides exploiting the stereochemical diversity of a central sugar
    • Sutherlin, D.P.; Armstrong, R.W. The synthesis of C-trisaccharides exploiting the stereochemical diversity of a central sugar. J. Am. Chem. Soc. 1996, 118, 9802-9803.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9802-9803
    • Sutherlin, D.P.1    Armstrong, R.W.2
  • 8
    • 0001199729 scopus 로고    scopus 로고
    • Synthesis of 12 stereochemically and structurally diverse C-trisaccharides
    • Sutherlin, D.P.; Armstrong, R.W. Synthesis of 12 stereochemically and structurally diverse C-trisaccharides. J. Org. Chem. 1997, 62, 5267-5283.
    • (1997) J. Org. Chem. , vol.62 , pp. 5267-5283
    • Sutherlin, D.P.1    Armstrong, R.W.2
  • 9
    • 0035812397 scopus 로고    scopus 로고
    • A unified approach to differentially linked β-C-disaccharides by ring-closing metathesis
    • Liu, L.; Postema, M.H.D. A unified approach to differentially linked β-C-disaccharides by ring-closing metathesis. J. Am. Chem. Soc. 2001, 123, 8602-8603.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 8602-8603
    • Liu, L.1    Postema, M.H.D.2
  • 10
    • 0038617365 scopus 로고    scopus 로고
    • Synthesis and partial biological evaluation of a small library of differentially-linked β-C-disaccharides
    • Postema, M.H.D.; Piper, J.L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. Synthesis and partial biological evaluation of a small library of differentially-linked β-C-disaccharides. J. Org. Chem. 2003, 68, 4748-4754.
    • (2003) J. Org. Chem. , vol.68 , pp. 4748-4754
    • Postema, M.H.D.1    Piper, J.L.2    Liu, L.3    Shen, J.4    Faust, M.5    Andreana, P.6
  • 11
    • 0031034008 scopus 로고    scopus 로고
    • New access to C-disaccharide analogs of α,α-trehalose using aqueous hetero Diels-Alder reaction
    • Lubineau, A.; Grand, E.; Scherrmann, M.-C. New access to C-disaccharide analogs of α,α-trehalose using aqueous hetero Diels-Alder reaction. Carbohydr. Res. 1997, 297, 169-174.
    • (1997) Carbohydr. Res. , vol.297 , pp. 169-174
    • Lubineau, A.1    Grand, E.2    Scherrmann, M.-C.3
  • 12
    • 33746672456 scopus 로고    scopus 로고
    • Synthesis of normuramic acid carba analog and its glycopeptide derivative resistant to β-elimination splitting of the side chain
    • Ledvina, M.; Pavelova, R.; Rohlenova, A.; Jezek, J.; Saman, D. Synthesis of normuramic acid carba analog and its glycopeptide derivative resistant to β-elimination splitting of the side chain. Collect. Czech. Chem. Commun. 2000, 65, 1726-1736.
    • (2000) Collect. Czech. Chem. Commun. , vol.65 , pp. 1726-1736
    • Ledvina, M.1    Pavelova, R.2    Rohlenova, A.3    Jezek, J.4    Saman, D.5
  • 13
    • 84912488909 scopus 로고
    • Organic sulfur compounds. XVI. (Thermal) rearrangement of thionocarbonic esters into thiolcarbonic esters
    • Schönberg, A.; Vargha, L. Organic sulfur compounds. XVI. (Thermal) rearrangement of thionocarbonic esters into thiolcarbonic esters. Chem. Ber. 1930, 63B, 178-180.
    • (1930) Chem. Ber. , vol.63 B , pp. 178-180
    • Schönberg, A.1    Vargha, L.2
  • 14
    • 85172014955 scopus 로고
    • Acetone-sugar. X. 3-Thioglucose
    • Freudenberg, K.; Wolf, A. Acetone-sugar. X. 3-Thioglucose. Chem. Ber. 1927, 60B, 232-238.
    • (1927) Chem. Ber. , vol.60 B , pp. 232-238
    • Freudenberg, K.1    Wolf, A.2
  • 15
    • 33947299993 scopus 로고
    • Nucleophilic displacement in 1,2:5,6-di-O-isopropylidene-3-O-(p- tolylsulfonyl)-α-D-glucofuranose
    • Nayak, U.G.; Whistler, R.L. Nucleophilic displacement in 1,2:5,6-di-O-isopropylidene-3-O-(p-tolylsulfonyl)-α-D-glucofuranose. J. Org. Chem. 1969, 34, 3819-3822.
    • (1969) J. Org. Chem. , vol.34 , pp. 3819-3822
    • Nayak, U.G.1    Whistler, R.L.2
  • 16
    • 0032542121 scopus 로고    scopus 로고
    • A practical modification of Barton-McCombie reaction and radical O- to S-rearrangement of xanthates
    • Quiclet-Sire, B.; Zard, S.Z. A practical modification of Barton-McCombie reaction and radical O- to S-rearrangement of xanthates. Tetrahedron Lett. 1998, 39, 9435-9438.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 9435-9438
    • Quiclet-Sire, B.1    Zard, S.Z.2
  • 17
    • 0029912413 scopus 로고    scopus 로고
    • An efficient rearrangement of secondary alkyl S-methyl xanthates by trimethylaluminum (TMA)
    • Barton, D.H.R.; Choi, S.-Y. An efficient rearrangement of secondary alkyl S-methyl xanthates by trimethylaluminum (TMA). Tetrahedron Lett. 1996, 37, 2695-2698.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2695-2698
    • Barton, D.H.R.1    Choi, S.-Y.2
  • 18
    • 0000896969 scopus 로고
    • A new annulated furanoses: A new free-radical isomerization of an S-methyl hex-5-enylxanthate to an S-(cyclopentylmethyl) S-methyl dithiocarbonate
    • Marco-Contelles, J.; Ruiz-Fernández, P.; Sánchez, B. A new annulated furanoses: a new free-radical isomerization of an S-methyl hex-5-enylxanthate to an S-(cyclopentylmethyl) S-methyl dithiocarbonate. J. Org. Chem. 1993, 58, 2894-2898.
    • (1993) J. Org. Chem. , vol.58 , pp. 2894-2898
    • Marco-Contelles, J.1    Ruiz-Fernández, P.2    Sánchez, B.3
  • 19
    • 0026738595 scopus 로고
    • The invention of radical reactions. Part XXIV. Relative rates of acylation and radical deoxygenation of secondary alcohols
    • Barton, D.H.R.; Dorchak, J.; Jaszberenyi, J.Cs. The invention of radical reactions. Part XXIV. Relative rates of acylation and radical deoxygenation of secondary alcohols. Tetrahedron 1992, 48, 7435-7446.
    • (1992) Tetrahedron , vol.48 , pp. 7435-7446
    • Barton, D.H.R.1    Dorchak, J.2    Jaszberenyi, J.Cs.3
  • 20
    • 37049083508 scopus 로고
    • Electron spin resonance spectroscopic investigation of carbohydrate radicals. Part 3. Conformation in deoxypyranosan-2-, -3-, and -4-yl radicals
    • Korth, H.-G.; Sustmann, R.; Gröninger, K.S.; Witzel, T.; Giese, B. Electron spin resonance spectroscopic investigation of carbohydrate radicals. Part 3. Conformation in deoxypyranosan-2-, -3-, and -4-yl radicals. J. Chem. Soc. Perkin Trans. II 1986, 1461-1464.
    • (1986) J. Chem. Soc. Perkin Trans. II , pp. 1461-1464
    • Korth, H.-G.1    Sustmann, R.2    Gröninger, K.S.3    Witzel, T.4    Giese, B.5
  • 21
    • 0028086078 scopus 로고
    • Radical-based deoxygenation of aliphatic alcohols via thioxocarbamate derivatives
    • Oba, M.; Nishiyama, K. Radical-based deoxygenation of aliphatic alcohols via thioxocarbamate derivatives. Tetrahedron 1994, 50, 10193-10200.
    • (1994) Tetrahedron , vol.50 , pp. 10193-10200
    • Oba, M.1    Nishiyama, K.2
  • 22
    • 0015645167 scopus 로고
    • The behavior of some aldoses with 2,2-dimethoxypropane-N,N- dimethylformamide-p-toluenesulfonic acid. I. At room termperature (∼25°C)
    • Hasegawa, A.; Fletcher Jr., H.G. The behavior of some aldoses with 2,2-dimethoxypropane-N,N-dimethylformamide-p-toluenesulfonic acid. I. At room termperature (∼25°C). Carbohydr. Res. 1973, 29, 209-222.
    • (1973) Carbohydr. Res. , vol.29 , pp. 209-222
    • Hasegawa, A.1    Fletcher Jr., H.G.2
  • 25
    • 0028808903 scopus 로고
    • Radical allylation of α-silyl acetic esters
    • Landais, Y.; Planchenault, D. Radical allylation of α-silyl acetic esters. Tetrahedron 1995, 51, 12097-12108.
    • (1995) Tetrahedron , vol.51 , pp. 12097-12108
    • Landais, Y.1    Planchenault, D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.