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Volumn 59, Issue 47, 2003, Pages 9349-9360

C-Glycosylidene derivatives (exo-glycals): Their synthesis by reaction of protected sugar lactones with tributylphosphonium ylids, conformational analysis and stereoselective reduction

Author keywords

C glycosylidene derivatives; Galactosylidene derivatives; Tributylphosphonium ylids

Indexed keywords

3,7 ANHYDRO 4,5,6,8 TETRA O BENZYL 2 DEOXY DEXTRO GALACTOOCT 2 ENONIC ACID METHYL ESTER; 3,7 ANHYDRO 4,5,6,8 TETRA O BENZYL 2 DEOXY DEXTRO GALACTOOCT 2 ENONIC ACID TERT BUTYL ESTER; 3,7 ANHYDRO 4,5,6,8 TETRA O BENZYL 2 DEOXY DEXTRO GALACTOOCT 2 ENONONITRILE; 3,7 ANHYDRO 4,5,6,8 TETRA O BENZYL 2 DEOXY DEXTRO GLUCOOCT 2 ENOMIC ACID METHYL ESTER; 3,7 ANHYDRO 4,5,6,8 TETRA O BENZYL 2 DEOXY DEXTRO GLUCOOCT 2 ENOMIC ACID TERT BUTYL ESTER; 3,7 ANHYDRO 4,5,6,8 TETRA O BENZYL 2 DEOXY DEXTRO GLUCOOCT 2 ENONIC ACID METHYL ESTER; 3,7 ANHYDRO 4,5,6,8 TETRA O BENZYL 2 DEOXY DEXTRO GLUCOOCT 2 ENONONITRILE; ACETONITRILE DERIVATIVE; ALKENE DERIVATIVE; BENZYL DERIVATIVE; CARBOHYDRATE DERIVATIVE; GALACTOSE; GLUCOSYLIDENEACETONITRILE; GLYCOSIDE; LACTONE DERIVATIVE; PHOSPHONIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0142184458     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.081     Document Type: Article
Times cited : (17)

References (22)
  • 1
    • 0000046979 scopus 로고    scopus 로고
    • For recent reviews on glycoamino acids see: e.g. (a) Schweizer F. Angew Chem. Int. Ed. 41:2002;230-253 (b) Gruner S.A.W., Locardi E., Lohof E., Kessler H. Chem. Rev. 102:2002;491-514.
    • (2002) Angew Chem. Int. Ed. , vol.41 , pp. 230-253
    • Schweizer, F.1
  • 2
    • 0036462603 scopus 로고    scopus 로고
    • For recent reviews on glycoamino acids see: e.g. (a)
    • For recent reviews on glycoamino acids see: e.g. (a) Schweizer F. Angew Chem. Int. Ed. 41:2002;230-253 (b) Gruner S.A.W., Locardi E., Lohof E., Kessler H. Chem. Rev. 102:2002;491-514.
    • (2002) Chem. Rev. , vol.102 , pp. 491-514
    • Gruner, S.A.W.1    Locardi, E.2    Lohof, E.3    Kessler, H.4
  • 7
    • 33748725769 scopus 로고    scopus 로고
    • (a) Lakhrissi M., Chapleur Y. Angew Chem., Int. Ed. 35:1996;750-752 (b) Lakhrissi Y., Taillefumier C., Lakhrissi M., Chapleur Y. Tetrahedron: Asymmetry. 11:2000;417-421.
    • (1996) Angew Chem., Int. Ed. , vol.35 , pp. 750-752
    • Lakhrissi, M.1    Chapleur, Y.2
  • 10
  • 11
    • 0001650014 scopus 로고    scopus 로고
    • For a review of synthetic applications of the non-classical Wittig reaction see:
    • For a review of synthetic applications of the non-classical Wittig reaction see: Murphy P.J., Lee S.E. J. Chem. Soc., Perkin Trans. 1. 1999;3049-3066.
    • (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 3049-3066
    • Murphy, P.J.1    Lee, S.E.2
  • 16
    • 0035857259 scopus 로고    scopus 로고
    • (a) Bérces A., Whitfield D.M., Nukada T. Tetrahedron. 57:2001;477-491 (b) http://www.nrc.ca/ibs/6ring.html . The conformation of a six-membered ring can be expressed in spherical polar co-ordinates such that d indicates the amount of puckering; θ=0 or 180° corresponds to a chair; θ=90°, φ=60n (where n=0, 1, 2...) corresponds to a boat and θ=90°, φ=60(n+0.5) corresponds to a twist-boat. (Z)-4c gives d=0.92; φ=76° θ=88°.
    • (2001) Tetrahedron , vol.57 , pp. 477-491
    • Bérces, A.1    Whitfield, D.M.2    Nukada, T.3
  • 17
    • 0035857259 scopus 로고    scopus 로고
    • The conformation of a six-membered ring can be expressed in spherical polar co-ordinates such that d indicates the amount of puckering; θ=0 or 180° corresponds to a chair; θ=90°, φ=60n (where n=0, 1, 2...) corresponds to a boat and θ=90°, φ=60(n+0.5) corresponds to a twist-boat. (Z)-4c gives d=0.92; φ=76° θ=88°.
    • (a) Bérces A., Whitfield D.M., Nukada T. Tetrahedron. 57:2001;477-491 (b) http://www.nrc.ca/ibs/6ring.html . The conformation of a six-membered ring can be expressed in spherical polar co-ordinates such that d indicates the amount of puckering; θ=0 or 180° corresponds to a chair; θ=90°, φ=60n (where n=0, 1, 2...) corresponds to a boat and θ=90°, φ=60(n+0.5) corresponds to a twist-boat. (Z)-4c gives d=0.92; φ=76° θ=88°.
  • 19
    • 85030958670 scopus 로고    scopus 로고
    • (Z)-5c gives d=0.88; φ=9° θ=168° when analysed by the methods of Ref. 13
    • (Z)-5c gives d=0.88; φ=9° θ=168° when analysed by the methods of Ref. 13.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.