Epoxidation and Bis-hydroxylation of C-Phenyl-Δ2,3-glyco-pyranosides.

Molecules

Ghada Fakha¹ 

[1] id="af1-molecules-10-00859">Laboratoire de Synthèse Asymétrique, UMR 5181, CPE Lyon, Université Claude Bernard Lyon 1, 43, Boulevard du 11 novembre 1918, 69622 Villeurbanne, France. Tel. [phone], Fax [phone]

关键词: (2;    3-Unsaturated-glycopyranosyl)benzene;    epoxidation;    cis-hydroxylation;   

DOI  :  10.3390/10080859

来源: mdpi

【 摘 要 】

Epoxidation and cis-hydroxylation of C-phenyl-Δ^2,3-glycopyranosides have been carried out with a view to developing C-aryl glycoside synthesis. Epoxidation of (2,3- dideoxy-d-erythro-hex-2-enopyranosyl)benzene and (6-O-tert-butyldimethylsilyl-2,3- dideoxy-d-erythro-hex-2-enopyranosyl)benzene gave predominantly the allo-adducts whatever the configuration at the anomeric center. Epoxidation of (4,6-di-O-tert-butyl-dimethylsilyl-2,3-dideoxy-d-erythro-hex-2-enopyranosyl)benzene gave the manno- and allo-adducts in a 89:11 and 40:60 ratios for the α- and β-anomers, respectively. Hydroxylation of α-C-phenyl-Δ^2,3-glycopyranosides using OsO₄ afforded the manno-adduct only, whatever the substituents at positions 4 and 6, whereas hydroxylation of (2,3-dideoxy- β-d-erythro-hex-2-enopyranosyl)benzene and (4,6-di-O-tert-butyldimethylsilyl-2,3- dideoxy- β-d-erythro-hex-2-enopyranosyl)benzene gave the manno- and allo-adducts in 25:75 and 80:20 ratios, respectively.

【 授权许可】

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