TIPS group-assisted isomerization of benzyl protected d-manno- and d-glucopyranose to d-fructofuranose derivatives

Carbohydr Res. 2023 Sep 21;534:108942. doi: 10.1016/j.carres.2023.108942. Online ahead of print.ABSTRACTBase-promoted (MeONa in MeOH or imidazole in DMF) isomerization of a series of 3,4,6-tri-O-benzyl-d-gluco- and d-mannopyranose derivatives with triisopropylsilyl (TIPS) substituents was studied. The presence of a bulky TIPS group at O-1 or O-2 was shown to be favorable for the isomerization of benzyl protected d-gluco- and d-mannopyranose derivatives to d-fructofuranose derivatives, in which the bulky silyl group occupies less sterically hindered primary position. The highest yield (33%) of the fructofuranose derivative was achieved when 3,4,6-tri-O-benzyl-2-O-triisopropylsilyl-d-mannopyranose was treated with MeONa in MeON at 50 °C.PMID:37769375 | DOI:10.1016/j.carres.2023.108942

Source: Carbohydrate Research - September 28, 2023 Category: Genetics & Stem Cells Authors: Maxim Y Karpenko Polina I Abronina Alexander I Zinin Alexander O Chizhov Leonid O Kononov Source Type: research