First Synthesis of a Series of New Natural Glucosides

Alkyl glucoside 1 and aryl glycosides 2–4 were highly stereospecifically synthesized over 4–6 steps from commercially available starting materials. The coupling reaction of the acetobromo-α-D-glucose with the unprotective dihydroxy aglycon in the presence of silver oxide, or with aromatic aglycon in the presence of sodium hydroxide produced the key intermediate. Only β-configuration glycosides were formed in this procedure. The synthesis of all these glycosides was reported for the first time.