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Volumn 47, Issue 38, 2006, Pages 6907-6909

First synthesis of indirubin N-glycosides (red sugars)

Author keywords

Indirubin; N Glycosides; N Glycosyl anilines; N Glycosyl isatines; N Heterocycles

Indexed keywords

ACETIC ACID DERIVATIVE; GLYCOSIDE; N (BETA DEXTRO GALACTOPYRANOSYL)INDIRUBIN; N (BETA DEXTRO MANNOPYRANOSYL)INDIRUBIN; N (BETA DEXTRO RHAMNOPYRANOSYL)INDIRUBIN; N (BETA DEXTRO RIBOPYRANOSYL)INDIRUBIN; N (BETA LEVO RHAMNOPYRANOSYL)INDIRUBIN; UNCLASSIFIED DRUG;

EID: 33747192579     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.024     Document Type: Article
Times cited : (19)

References (20)
  • 12
    • 33747171013 scopus 로고    scopus 로고
    • Indirubin, the red shade of indigo. In Life in Progress; Meijer, L., Guyard, N., Skaltsounis, L. A., Eisenbrand, G., Ed.; Station Biologique, Roscoff, in press.
  • 17
    • 33747184664 scopus 로고    scopus 로고
    • note
    • 11 N-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)isatine and N-(2,3,4,6-tetra-O-acetyl-β-d-mannopyranosyl)isatine were carried out following the procedure as described above. In contrast, isomerically enriched β-anomers (β/α >5:1) were employed as starting materials. Starting with N-(2,3,4,6-tetra-O-acetyl-α,β-d-glucopyranosyl)aniline (1.00 g, 2.36 mmol), N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)isatine was isolated (0.34 g, 30%). N-(2,3,4-Tri-O-acetyl-α,β-d-ribopyranosyl)aniline (0.75 g, 2.13 mmol) was transformed into N-(2,3,4-tri-O-acetyl-β-d-ribopyranosyl)isatine (0.18 g, 21%). Starting with N-(2,3,4,6-tetra-O-acetyl-α,β-d-galactopyranosyl)aniline (0.80 g, 1.89 mmol), N-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)isatine was isolated (0.47 g, 52%). N-(2,3,4,6-Tetra-O-acetyl-α,β-d-mannopyranosyl)aniline (1.00 g, 2.36 mmol) was transformed into N-(2,3,4,6-tetra-O-acetyl-β-d-mannopyranosyl)isatine (0.24 g, 21%). All products were purified by column chromatography (heptane/EtOAc = 2:1).
  • 20
    • 33747173865 scopus 로고    scopus 로고
    • note
    • 3-MeOH, 20:1→10:1) yielded 9β (100 mg, 59%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.