Short synthesis of a benzyl ether-protected building block for the synthesis of carbocyclic galactopyranose mimics.
A versatile intermediate for the synthesis of galactose-mimicking carbasugars was synthesised from tetrabenzyl galactose in five steps and 30% overall yield. The reaction sequence uses an L-proline-mediated aldol reaction as key step. The reaction sequence was run on several grams of material.
Cumpstey
Ian
I
Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden. ian.cumpstey@sjc.oxon.org
D000447:Aldehydes / Q000737:chemistry; D054329:Carbasugars / Q000138:chemical synthesis* / Q000737:chemistry*; D053138:Cyclohexenes / Q000737:chemistry; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry*; D006595:Hexosamines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D000447:Aldehydes; D054329:Carbasugars; D053138:Cyclohexenes; D006595:Hexosamines; C030791:valienamine; C116609:3-hydroxybutanal; D005690:Galactose