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Volumn , Issue 24, 2009, Pages 4143-4148

Stereoselective synthesis of novel N-b-glycosyl sulfonamides by sulfonamidoglycosylation of per-O-acetylated sugars

Author keywords

stereoselectivity; Exo anomeric effect; Per O acetylated carbohydrates; Sulfonamides; Sulfonamidoglycosylation

Indexed keywords

ACETYLATED SUGARS; ANOMERIC EFFECT; ANOMERICS; GLYCOSYL; GOOD YIELD; N-GLYCOSYL SULFONAMIDES; PER-O-ACETYLATED CARBOHYDRATES; STEREOSELECTIVE SYNTHESIS; SULFONAMIDES; SULFONAMIDOGLYCOSYLATION;

EID: 77958054104     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217045     Document Type: Article
Times cited : (17)

References (24)
  • 3
    • 0029739240 scopus 로고    scopus 로고
    • Danishefsky's group reported on the reaction of glycals with iodonium di-sym-collidine perchlorate and benzenesulfon-amide to afford 2-b-iodo-1-a-sulfonamidohexose in a stereoselective manner. These glycosylsulfonamides were used for the preparation of oligosaccharides containing a 2-aminohexose subunit. For a review, see: Danishefsky, S. J.; Bilodeau M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1380
    • Danishefsky, S.J.1    Bilodeau, M.T.2
  • 16
    • 0033953820 scopus 로고    scopus 로고
    • C1-H1 coupling constants of 149-154 Hz while those of the a-anomers occur at around 166 Hz, see: Crich, D.; Li, H. J. Org. Chem. 2000, 65, 801.
    • (2000) J. Org. Chem. , vol.65 , pp. 801
    • Crich, D.1    Li, H.2
  • 19
    • 33846553079 scopus 로고    scopus 로고
    • An open-chain anomerization mechanism was also proposed as an explanation for the stereoselectivity in the Lewis acid catalysed reactions of peracetylated sugars with MeCN to afford N-b-D-glycosyl amides, see: Song, X.; Hollingsworth, R. I. Synlett 2006, 3451.
    • (2006) I. Synlett , pp. 3451
    • Song, X.1    Hollingsworth, R.2
  • 20
    • 78650742697 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra of the crude reaction mixtures showed only the presence of b-sulfonamidomanno-pyranoside and unreacted per-O-acetylated manno-pyranoside.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.