153124-47-1

Upstream product

• 121195-27-5 2,4-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol 

Downstream Products

• 209348-44-7 (6R,7S,8R,8aR)-6,8-Bis-benzyloxy-7-hydroxy-hexahydro-oxazolo[3,4-a]pyridin-3-one 
• 209345-58-4 Methanesulfonic acid (6R,7S,8R,8aR)-6,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-7-yl ester 
• 209345-53-9 Acetic acid (6R,7S,8R,8aR)-6,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-7-yl ester 
• 209345-55-1 (6R,7S,8R,8aR)-6,8-Bis-benzyloxy-7-methoxymethoxy-hexahydro-oxazolo[3,4-a]pyridin-3-one 
• 209345-56-2 C₂₁H₁₉NO₇ 
• 209345-61-9 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((6R,7R,8R,8aR)-6,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-7-yloxy)-tetrahydro-thiopyran-3-yl ester 
• 209345-52-8 Trifluoro-methanesulfonic acid (6R,7R,8R,8aR)-6,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-7-yl ester 

Relevant academic research and scientific papers

Inhibitors of endo-α-mannosidase. Part II. 1-Deoxy-3-O-(α-D-glucopyranosyl)-mannojirimycin and congeners modified in the mannojirimycin unit

The syntheses of 1-deoxy-3-O-(α-D-glucopyranosyl)-mannojirimycin (9) and its 2-deoxy, 2-O-methyl, 4-deoxy, 4-O-methyl, 6-deoxy, 6-O-methyl, N-methyl, and N-propyl congeners are described. Since 9 was previously shown to effectively inhibit endo-α-D-mannosidase, a glycoprotein-processing hydrolase, these chemical modifications were designed to assist in the assessment of intermolecular hydrogen bonds of the inhibitor-enzyme complex. The previously reported data require that all hydroxyl groups of the deoxymannojirimycin unit of 9 namely, OH-2, OH-4, OH-6, and also the NH-5 group, interact with charged and polar groupings of the enzyme since deoxygenations and alkylations abolished or significantly reduced activities. Conformational analysis of 9 and some of its congeners based on NMR chemical shifts, experimental and theoretical nuclear Overhauser enhancements and HSEA calculations were performed. The chemical modifications of the glucose unit of 9 are described in the accompanying paper.