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Volumn 69, Issue 17, 2004, Pages 5774-5777

Silver(I) oxide mediated selective monoprotection of diols in pyranosides

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; POTASSIUM COMPOUNDS; REACTION KINETICS; STOICHIOMETRY;

EID: 4143142046     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0497252     Document Type: Article
Times cited : (75)

References (39)
  • 35
    • 4143110833 scopus 로고    scopus 로고
    • note
    • The reaction of mannose derivative 7 with BzCl was also tried. The desired monobenzoylated product was too unstable to purify by column chromatography. The benzoyl group migrated from one hydroxyl to another hydroxyl position during standing and separation process, and we finally got the mixture of 2- and 3-benzoylated product in a ratio of ∼1:1.
  • 36
    • 4143107472 scopus 로고    scopus 로고
    • note
    • In contrast, we treated methyl 4,6-O-benzylidene-β-D-glucopyranoside (4) with TsCl and pyridine, the 3-tosylated product was isolated in 48% yield as the major product.
  • 37
    • 4143066394 scopus 로고    scopus 로고
    • note
    • Using ethyl acetate, toluene, or 1,2-dichloroethane as solvent, similar results (yields and product ratios) were also obtained. Because 1,2-dichloroethane is more toxic and the solubility of saccharides in ethyl acetate or toluene is not good, we eventually chose dichloromethane as the solvent to perform the reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.