1233944-58-5

Upstream product

• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 291753-79-2 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-α-D-manno-pyranoside 
• 52290-43-4 methyl 6-deoxy-6-iodo-α-D-mannopyrannoside 
• 155049-46-0 methyl 2,3,4-tri-O-benzyl-5-methylene-α-D-lyxopyranoside 

Downstream Products

• 1152509-47-1 (3S,4R,5R)-3,4,5-tris(benzyloxy)-1-(6-hydroxyhexyl)piperidin-2-one 
• 1152509-46-0 (3S,4R,5R)-3,4,5-tris(benzyloxy)-1-decylpiperidin-2-one 
• 1228764-28-0 (3S,4R,5R)-3,4,5-tris(benzyloxy)-1-(but-3-enyl)piperidin-2-one 
• 1228764-29-1 (3S,4R,5R)-3,4,5-tris(benzyloxy)-1-(pent-4-enyl)piperidin-2-one 
• 1228764-27-9 (3S,4R,5R)-1-allyl-3,4,5-tris(benzyloxy)piperidin-2-one 
• 1233965-58-6 (3R,5R)-3,4,5-tris(benzyloxy)-1-decylpiperidine 

Relevant academic research and scientific papers

Vinyl Grignard-Mediated Stereoselective Carbocyclization of Lactone Acetals

A novel Ferrier-type carbocyclization is reported. It involves a carbohydrate-derived lactone acetal synthesized from methyl α-d-glucopyranoside, which upon treatment with excess vinylmagnesium bromide provides a highly substituted carbocyclic product as a single stereoisomer. The yield is greatly increased when N,N,N′,N′-tetramethylethylenediamine is added to the reaction mixture. Optimized reaction conditions have been applied to lactone acetals derived from other carbohydrates. Based on the obtained results, a possible reaction mechanism has been proposed. Furthermore, scalability of the reaction up to 15 g scale and derivatization of the carbocyclic product has been demonstrated, including the formation of a rare trans-bicyclo[4.3.0]nonene scaffold via a ring-closing metathesis. The structure of this and all carbocyclic products were confirmed by X-ray crystallographic analysis.

NOVEL MANNOPYRANOSIDE DERIVATIVES WITH ANTICANCER ACTIVITY

The present invention relates to mannopyranoside-derived compounds and to the use thereof as medicaments, in particular in the treatment of cancer diseases, and also to the method for preparing same and to pharmaceutical compositions comprising such compo

Synthetic N-alkylated iminosugars as new potential immunosuppressive agents

The new emerging immunosuppressive effects displayed by iminosugars have not been much investigated so far. Several new N-alkyl dideoxy iminoalditols were designed and synthesized to explore their immunosuppressive effects. These iminosugars inhibited the

A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides

A facile, versatile and stereoselective synthesis of bicyclic polyhydroxylated alkaloids as castanospermine analogues is described. The synthetic route started from methyl pyranosides. The key steps involved a high-yielding expeditious one-pot tandem reaction from alkenes to N-substituted δ-lactams. The δ-lactams were stereoselectively vinylated to give the dienes, which were followed by the ring-closing metathesis to produce the cyclized products. The functional group transformations of the resulting bicyclic compounds furnished diverse polyhydroxylated alkaloids in good yields. The Royal Society of Chemistry 2010.

Rational design and synthesis of highly potent pharmacological chaperones for treatment of N370S mutant Gaucher disease

Highly potent N-substituted δ-lactams have been rationally designed and synthesized by a concise route with a one-pot tandem reaction as key step. These iminosugars show weak inhibition of wildtype β-glucocerebrosidase but 3- to 6-fold increases in mutant