385836-99-7

Upstream product

• 100-51-6 benzyl alcohol 
• 77-76-9 2,2-dimethoxy-propane 
• 113278-68-5 2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid 

Downstream Products

• 42491-79-2 (2S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxypropanoic acid 
• 1429470-98-3 benzyl (5R)-2,2-dimethyl-5-[(1E)-3-oxobut-1-en-1-yl]-1,3-oxazolidine-3-carboxylate 
• 1429470-99-4 benzyl (5R)-2,2-dimethyl-5-[(1Z)-3-oxobut-1-en-1-yl]-1,3-oxazolidine-3-carboxylate 
• 134038-73-6 benzyl (S)-5-hydroxymethyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 135582-88-6 (S)-3-benzyloxycarbonyl-5-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine 
• 134038-74-7 benzyl (S)-5-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 1429471-04-4 benzyl (5S)-5-[(1R,2R)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 1429471-03-3 benzyl (5S)-5-[(1S,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 1429470-96-1 benzyl (5S)-5-[(1S,2R)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 1429470-97-2 benzyl (5S)-5-[(1R,2S)-1,2-dihydroxy-3-oxobutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 135582-87-5 (S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxypropanoate 

Relevant academic research and scientific papers

Organocatalytic syn-aldol reactions of hydroxy ketones with (S)-isoserinal: Asymmetric synthesis of 6-deoxy-1,5-iminohexitols and related compounds

An improved and convenient preparation of protected (S)-isoserinal on a large scale is reported. This key intermediate was reacted through organocatalyzed aldol reaction or Wittig based chain extension and functionalization to give enantiopure 1,5,6-trideoxy-1,5-imino-hexitols such as 10a (L-manno) and 10b (D-gluco). These two compounds are of interest as glycosidase inhibitors. The elaborated organocatalytic process includes diastereoselective syn aldol reaction of (S)-isoserinal hydrate and hydroxyacetone or 1-hydroxy-2-octanone and is promoted by various amino acid-based catalysts. Diastereoselectivities of up to 8:1 were achieved, thus establishing a new, efficient synthetic route to these important carbohydrate mimics. A novel protocol for the preparation of 1,5,6-trideoxy-1,5-imino-L- mannitol and 1,5,6-trideoxy-1,5-imino-D-glucitol is reported. The key steps include organocatalyzed syn-selective direct aldol reaction of hydroxyacetone and CBz-protected isoserinal hydrate, followed by reductive amination/ cyclization. Copyright

Novel glucagon receptor antagonists with improved selectivity over the glucose-dependent insulinotropic polypeptide receptor

Optimization of a new series of small molecule human glucagon receptor (hGluR) antagonists is described. In the process of optimizing glucagon receptor antagonists, we counter-screened against the closely related human gastric inhibitory polypeptide receptor (hGIPR), and through structure activity analysis, we obtained compounds with low nanomolar affinities toward the hGluR, which were selective against the hGIPR and the human glucagon-like peptide-1 receptor (hGLP-1R). In the best cases, we obtained a >50 fold selectivity for the hGluR over the hGIPR and a >1000 fold selectivity over the hGLP-1R. A potent and selective glucagon receptor antagonist was demonstrated to inhibit glucagon-induced glycogenolysis in primary rat hepatocytes as well as to lower glucagon-induced hyperglycemia in Sprague - Dawley rats. Furthermore, the compound was shown to lower blood glucose in the ob/ob mouse after oral dosing.

Glucagon antagonists/inverse agonists

A novel class of compounds, which act to antagonize the action of the glucagon hormone on the glucagon receptor. Owing to their antagonizing effect of the glucagon receptor the compounds may be suitable for the treatment and/or prevention of any diseases and disorders, wherein a glucagon antagonistic action is beneficial, such as hyperglycemia, Type 1 diabetes, Type 2 diabetes, disorders of the lipid metabolism, such as dyslipidemia, and obesity.