883143-13-3

Upstream product

• 883143-12-2 (1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane] 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 24850-33-7 allyltributylstanane 

Downstream Products

• 883143-17-7 methyl 2-oxo-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate 
• 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 
• 883143-16-6 ((2R,3R,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester 
• 883143-21-3 methyl (2S)-benzylamino-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate 
• 883143-19-9 methyl 2-benzyl imino-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate 
• 883143-20-2 ((2R,3R,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-[(Z)-benzylimino]-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 

Relevant academic research and scientific papers

Synthesis of Carbohydrate-Templated Amino Acids and Methods of Using Same

The present invention generally relates to tetrahydropyranyl-derivatized amino acids, their syntheses and their incorporation into peptides and peptidomimetics. The tetrahydropyran moiety constrains the side chain of an amino acid, thereby providing a molecule that may act as a sugar- or amino acid-mimetic as well as a scaffold for combinatorial synthesis.

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.