An unusual Wittig reaction with sugar derivatives: exclusive formation of a 4-deoxy analogue of α-galactosyl ceramide?
RSC Advances Pub Date: 2014-06-06 DOI: 10.1039/C4RA03369H
Abstract
The Wittig reaction of the pyrano-type reducing sugars undergoes an unexpected formation of dienes through the elimination of a benzyloxy group in the presence of t-BuOK. LiHMDS is used rather than t-BuOK to prevent alcohol elimination in the same sugar derivatives. Collectively, t-BuOK has unusual functions in the Wittig reaction that correspond with other bases such as LiHMDS, NaH, and n-BuLi. This unusual function of t-BuOK showed that a unique 4-deoxy-5-hydroxyl analogue 2 of α-galactosyl ceramide was formed exclusively.
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Journal Name：RSC Advances
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CAS no.: 89640-58-4
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