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Volumn 49, Issue 44, 2008, Pages 6356-6359

Synthesis of novel glycolipids derived from glycopyranosyl azides and N-(β-glycopyranosyl)azidoacetamides

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; AMIDE; AZIDE; CUPROUS ION; ETHER LIPID; GLUCOSE; GLYCOLIPID; GLYCOPYRANOSYL AZIDE; N (BETA GLYCOPYRANOSYL)AZIDOACETAMIDE; UNCLASSIFIED DRUG;

EID: 51749114007     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.08.073     Document Type: Article
Times cited : (27)

References (31)
  • 19
    • 51749109184 scopus 로고    scopus 로고
    • 2 (20 mol %, 1 M solution) and sodium ascorbate (40 mol %, 1 M solution) were added with stirring at room temperature. TLC analysis of the reaction mixture showed complete disappearance of the azide after 0.5-2 h. Following removal of the solvent using a rotoevaporator, the residue was extracted with ethyl acetate (3 × 20 mL). The ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated to dryness. The resulting syrupy product obtained was purified by flash column chromatography (10-50% ethyl acetate in hexane) over silica gel to furnish the title compounds.
    • 2 (20 mol %, 1 M solution) and sodium ascorbate (40 mol %, 1 M solution) were added with stirring at room temperature. TLC analysis of the reaction mixture showed complete disappearance of the azide after 0.5-2 h. Following removal of the solvent using a rotoevaporator, the residue was extracted with ethyl acetate (3 × 20 mL). The ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated to dryness. The resulting syrupy product obtained was purified by flash column chromatography (10-50% ethyl acetate in hexane) over silica gel to furnish the title compounds.
  • 22
    • 51749102255 scopus 로고    scopus 로고
    • 3, 400 MHz): δ
    • 3, 400 MHz): δ
  • 23
    • 51749121081 scopus 로고    scopus 로고
    • +. Found 396.2111.
    • +. Found 396.2111.
  • 26
    • 51749102256 scopus 로고    scopus 로고
    • 3, 400 MHz): δ 7.70 (s, 1H), 7.50 (s, 1H), 5.84 (d, 1H, J = 9.1 Hz, H-1), 5.48 (m, 1H, H-2), 5.42 (m, 1H, H-3), 5.06 (t, 1H, J = 9.6 Hz, H-4), 4.66 (dd, 1H, J = 2.4, 14.8 Hz, H-6b), 4.62 (s, 2H), 4.58 (s, 2H), 4.46 (dd, 1H, J = 7.6, 14.8 Hz
    • 3, 400 MHz): δ 7.70 (s, 1H), 7.50 (s, 1H), 5.84 (d, 1H, J = 9.1 Hz, H-1), 5.48 (m, 1H, H-2), 5.42 (m, 1H, H-3), 5.06 (t, 1H, J = 9.6 Hz, H-4), 4.66 (dd, 1H, J = 2.4, 14.8 Hz, H-6b), 4.62 (s, 2H), 4.58 (s, 2H), 4.46 (dd, 1H, J = 7.6, 14.8 Hz
  • 27
    • 51749121080 scopus 로고    scopus 로고
    • 2-), 1.59 (m, 4H), 1.40-1.20 (m, 20H), 0.90 (m, 6H, 2 ×
    • 2-), 1.59 (m, 4H), 1.40-1.20 (m, 20H), 0.90 (m, 6H, 2 ×
  • 29
    • 51749109183 scopus 로고    scopus 로고
    • 1H NMR
    • 1H NMR
  • 30
    • 51749102257 scopus 로고    scopus 로고
    • +. Found 487.3132.
    • +. Found 487.3132.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.