688764-97-8

Upstream product

• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 

Downstream Products

• 173170-20-2 (1R)-2,3,4,6-tetra-O-benzyl-5-O-(methylsulfonyl)-1-C-(1H-imidazol-2-yl)-D-glucitol 
• 173242-91-6 (1R)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-C-(1H-imidazol-2-yl)-D-glucitol 
• 173242-92-7 (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-C-(1H-imidazol-2-yl)-D-glucitol 

Relevant academic research and scientific papers

Synthesis and evaluation as glycosidase inhibitors of 1H-imidazol-2-yl C-glycopyranosides

The (1H-imidazol-2-yl)ulose 8 and the 1H-imidazol-2-yl C-glycopyranosides 23 and 24 have been prepared from tetra-O-benzylgluconolactone 6 in two and six steps, respectively. The imidazoles 8 and 24 are moderate competitive inhibitors of sweet-almond β-glucosidase (pH 6.8, K(i) ~ 0.79 and 0.64 mM, respectively), while 23 is a competitive inhibitor of yeast α-glucosidase (pH 6.8, K(i) ~ 0.26 mM). Addition of 2-lithiated 1-[(dimethylamino)methyl]-1H-imidazole to 6 gave the ulose 7 (68%), which was deprotected to 8. Reduction of 7 with NaBH4 yielded a 12:88 mixture 10/11. Attempts to selectively mesylate HO-C(1) of these diols failed, while dinitrobenzoylation led to 19/20, which cyclized easily (NaH) to a 25 :75 mixture of 21 and 22 which were separated and debenzylated to the C-glycosides 23 and 24.