208592-90-9

Upstream product

• 208592-84-1 (2R,3R,4R,5R)-2-Acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-hexanoic acid amide 
• 208592-88-5 N-((3R,4R,5S,6S)-4,5-Bis-benzyloxy-6-benzyloxymethyl-6-hydroxy-2-oxo-piperidin-3-yl)-acetamide 

Downstream Products

• 168037-66-9 (5R,6R,7R,8R)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine 
• 167904-24-7 (5R,6R,7R,8S)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine 
• 208592-93-2 (3R,4R,5R,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-2-oxo-piperidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

1,5-Dideoxy-1,5-imino-D-glucitol Compounds

1,5-Dideoxy-1,5-imino-D-glucitol compounds as shown in the specification. Also disclosed is a method of treating a hexosaminidase-associated disease.

Synthesis and Some Transformations of 2-Acetamido-5-amino-3,4,6-tri-O-benzyl-2,5-dideoxy-D-glucono-1,5-lactam

The lactam 21 was obtained in an overall yield of 72% from the hydroxy amide 16 by oxidation with the Dess-Martin periodinane, acid-catalysed isomerization of the oxidation products in toluene, whereupon 18/19 precipitated, and reductive dehydroxylation of 18/19 (Et3SiH/BF3 · OEt2; Scheme 1). The amide 16 was obtained by ammonolysis of the N-acetylglucosamine-derived lactone 15. Depending on the oxidation method, 16 yielded the keto amide 17, the hydroxy lactams 18/19, and the pyrrolidinecarboxamide 20 in widely different proportions. The pyrrolidinecarboxamide 20 was not reduced under the conditions of the reductive dehydroxylation. Hydrogenolysis of the benzyl-protected lactam 21 gave the trihydroxy lactam 22, while reduction with NaBH4/ BF3 · OEt2 led to the 2-acetamidopiperidine derivative 24 (Scheme 2). Selective (tert-butoxy)carbonylation of the lactam 21 (→ 25) followed by NaBH4 reduction and acid-catalysed solvolysis in EtOH led to the α-ethoxycarbamates 28/29. Similarly, (tert-butoxy)carbonylation of 1 (→ 31) followed by reduction to 32/33 and glycosidation yielded the ethoxycarbamate 34. Treatment of the GlcNAc-derived ethyl glycosides 28/29 with Me3SiCN/ BF3 · OEt2 gave the equatorial amino nitrile 30. Under similar conditions, the Glc-derived glycoside 34 led to the iminooxazolidinone 35. In the presence of a larger proportion of Me3SiCN at 5°, 34 was transformed into the axial, selectively monodebenzylated amino nitrile 36.