Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1390036 | Carbohydrate Research | 2016 | 5 Pages |
•Synthesis of pyranoid glycals using Zn/NH4Cl system.•High yields and short reaction time.•Simple operation and broad functional group compatibility.•Efficient synthesis of glucal in gram-scale amount.
A simple and efficient procedure was designed for the preparation of pyranoid glycals. In a novel fashion, a series of protected glycopyranosyl bromides underwent reductive elimination in the presence of zinc dust and ammonium chloride in CH3CN at 30–60 °C. The corresponding glycals were obtained with excellent isolated yields (72–96%) in a short time (20–50 min). Furthermore, the transformation was compatible with different protection patterns and conveniently scalable (86% for 45 g acetobromoglucose) which made it very applicable in organic synthesis.
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