883143-20-2

Upstream product

• 883143-13-3 ((2R,3R,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-trimethylsilanyloxy-acetic acid methyl ester 
• 883143-14-4 ((2S,3R,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hydroxy-acetic acid methyl ester 
• 883143-18-8 ((2S,3R,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-oxo-acetic acid methyl ester 
• 100-46-9 benzylamine 

Relevant academic research and scientific papers

Synthesis of spirocyclic glucose-proline hybrids (GlcProHs)

A short synthetic route to polyhydroxylated spirocyclic glucose-based L-proline analogues is described from easily prepared 2,3,4,6 tetra-O-benzyl-D-glucono-lactone. The synthesis involves C-glycosylation of an exocyclic glucose-based epoxide with allyltributylstannane that affords functionalized C-ketosides containing an α-hydroxy ester moiety. Oxidation of the alcohol function, followed by stereoselective reductive amination provides an amine that undergoes iodine-induced aminocyclization to provide spirocyclic glucose-proline hybrids bearing an iodomethylene side-chain. The iodo function of the side-chain can be converted into other functional groups such as ester and hydroxyl groups, thereby allowing additional modifications to the pyrrolidine ring. Georg Thieme Verlag Stuttgart.