Glycoside Synthesis from 1‐Oxygen Substituted Glycosyl Donors: Sections 3.3 and 3.4

Latent O‐glycosides, 2‐(2‐propylthiol)benzyl (PTB) glycosides, were converted into the corresponding active glycosyl donors, 2‐(2‐propylsulfinyl)benzyl (PSB) glycosides, by a simple and efficient oxidation. Treatment of the PSB donor and various acceptors with triflic anhydride provided the desired glycosides in good to excellent yields. The leaving group, which was activated by an interrupted Pummerer reaction, can be recycled (PSB‐OH) and regenerated as the precursor (PTB‐OH). A natural hepatoprotective glycoside, leonoside F, was efficiently synthesized in a convergent [3+1] manner with this newly developed method. The present total synthesis also led to a structural revision of this phenylethanoid glycoside.

show abstract

S‐Benzimidazolyl Glycosides as a Platform for Oligosaccharide Synthesis by an Active–Latent Strategy

Hasty

Kleine

Demchenko

2011

Angew Chem Int Ed

View full text Add to dashboard Cite

show abstract

Glycoside Synthesis from 1‐Oxygen Substituted Glycosyl Donors: Sections 3.3 and 3.4

Cited by 7 publications

References 195 publications

S‐Benzimidazolyl Glycosides as a Platform for Oligosaccharide Synthesis by an Active–Latent Strategy

S‐Benzimidazolyl Glycosides as a Platform for Oligosaccharide Synthesis by an Active–Latent Strategy

Interrupted Pummerer Reaction in Latent‐Active Glycosylation: Glycosyl Donors with a Recyclable and Regenerative Leaving Group

S‐Benzimidazolyl Glycosides as a Platform for Oligosaccharide Synthesis by an Active–Latent Strategy

Contact Info

Product

Resources

About