Abstract
AbstractWe have developed a versatile deprotection method for the synthesis of 2‐deoxyoligosaccharides containing a 1,4‐dialkylhydroquinone moiety at the anomeric position. The Birch reduction of a 2,6‐dideoxy monosaccharide with potassium and 1,3‐pentadiene gave the deprotected product without any undesired reduction. The utility of this method was then demonstrated in the Birch reduction of a landomycin E deoxytrisaccharide. Pd‐catalysed hydrogenation led to the anomerization, or cleavage, of the glycosidic linkages. In contrast, Birch reduction based on the optimized conditions followed by treatment with mCPBA (m‐chloroperoxybenzoic acid) provided the fully deprotected deoxytrisaccharide in 65 % overall yield. These results show that the Birch reduction is a powerful deprotection method for the synthesis of complex natural glycosides, including 2‐deoxyoligosaccharides.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
