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Volumn 8, Issue 2, 2006, Pages 297-299

Intramolecular benzyl protection delivery: A practical synthesis of DMDP and DGDP from D-fructose

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIDEOXY 2,5 IMINO D GLUCITOL; 2,5 DIDEOXY 2,5 IMINO D MANNITOL; 2,5-DIDEOXY-2,5-IMINO-D-GLUCITOL; 2,5-DIDEOXY-2,5-IMINO-D-MANNITOL; DRUG DERIVATIVE; ETHER DERIVATIVE; FRUCTOSE; GLYCOSIDASE; IMINOSUGAR; MANNITOL; SORBITOL;

EID: 31544469758     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052668u     Document Type: Article
Times cited : (31)

References (30)
  • 3
    • 26444578866 scopus 로고    scopus 로고
    • Some remarkable preparations of partially benzylated carbohydrate derivatives have been accomplished by an alternative strategy involving regioselective O-debenzylation. See, for example: (a) Bistri, O.; Sinaÿ, P.; Sollogoub, M. Tetrahedron Lett. 2005, 46, 7757.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 7757
    • Bistri, O.1    Sinaÿ, P.2    Sollogoub, M.3
  • 7
  • 17
    • 18344415504 scopus 로고    scopus 로고
    • For a very interesting approach to the synthesis of selectively functionalized DMDP derivatives, see: (a) Wrodnigg, T. A.; Stütz, A. E.; Withers, S. G. Tetrahedron 1997, 38, 5463.
    • (1997) Tetrahedron , vol.38 , pp. 5463
    • Wrodnigg, T.A.1    Stütz, A.E.2    Withers, S.G.3
  • 24
  • 25
    • 0032413194 scopus 로고    scopus 로고
    • Compound 5 can be prepared in one step from commercially available D-fructose by reaction with acetone in the presence of sulfuric acid (45% yield). See: Lichtenthaler, F. W. Carbohydr. Res. 1998, 313, 69.
    • (1998) Carbohydr. Res. , vol.313 , pp. 69
    • Lichtenthaler, F.W.1
  • 26
    • 37049125206 scopus 로고
    • For early, but remarkable, examples on the manipulation of D-fructose at C-5, see: (a) Murphy, D. J. Chem. Soc. C 1967, 1732.
    • (1967) J. Chem. Soc. C , pp. 1732
    • Murphy, D.1
  • 29
    • 0000507441 scopus 로고
    • For a discussion on the influence of polar and steric factors on the nucleophilic displacement of sulfonate esters, see: Richardson, A. C. Carbohydr. Res. 1969, 10, 395.
    • (1969) Carbohydr. Res. , vol.10 , pp. 395
    • Richardson, A.C.1
  • 30
    • 0042890584 scopus 로고    scopus 로고
    • The fact that efficient methods to access L-fructose have been recently reported additionally broadens the scope of this approach to access unnatural polyhydroxypyrrolidine derivatives. See: Franke, D.; Machajewski, T.; Hsu, C.-C.; Wong, C.-H. J. Org. Chem. 2003, 68, 6828.
    • (2003) J. Org. Chem. , vol.68 , pp. 6828
    • Franke, D.1    Machajewski, T.2    Hsu, C.-C.3    Wong, C.-H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.