Synthesis of Protected 3-Deoxy-3-fluoro- and 4-Deoxy-4-fluoro-d-galactopyranosides from Levoglucosan

摘要

src="http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/joceah/2017/joceah.2017.82.issue-9/acs.joc.7b00543/20170501/images/medium/jo-2017-00543r_0006.gif">Fluorinated carbohydrates are invaluable tools to study various biochemical processes. Herein, we describe a new strategy to access orthogonally protected 3-deoxy-3-fluorogalactopyranose and acetylated 4-deoxy-4-fluorogalactopyranose. Starting from inexpensive levoglucosan, most reactions were performed on a gram scale and allowed excellent regio- and stereocontrol with a minimal use of protection/deprotection cycles. Hence, we developed practical alternatives to the decade-long reported method to access both 3-deoxy-3-fluoro- and 4-deoxy-4-fluorogalactopyranose.