144848-73-7

Upstream product

• 217309-46-1 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose 
• 177493-29-7 5-O-(tert-butyldimethylsilyl)2,3-di-O-isopropylidene-D-ribitol 
• 177569-80-1 ((3aR,4S,6aS)-5-benzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl)methanol 
• 144848-66-8 (3S,4R,5R)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine 
• 18908-34-4 5-amino-5-deoxy-2,3-O-isopropylidene-D-ribono-1,5-lactam 
• 100-39-0 benzyl bromide 
• 177493-30-0 5-O-(tert-butyldimethylsilyl)-1,4-bis(methanesulfonyl)-2,3-di-O-isopropylidene-D-ribitol 
• 177569-79-8 (3aR,4S,6aS)-5-benzyl-4-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole 
• 177493-31-1 (2S,3R,4S)-<1-Benzyl-3,4-(isopropylidenedioxy)pyrrolidin-2-yl>methyl methanesulfonate 
• 144848-72-6 (3R,4R,5S)-1-Benzyl-4,5-(isopropylidenedioxy)piperidin-3-ol 

Downstream Products

• 177493-27-5 (3S,4S,5R)-1-Benzyl-5-fluoropiperidin-3,4-diol 

Relevant academic research and scientific papers

Preparation of optically active 3-substituted piperidines via ring expansion: Synthesis of 4-amino- and 4-fluoro-1,4,5-trideoxy-1,5-imino-D-ribitol and 1,5-dideoxy-1,5-imino-D-ribitol

A new method for the preparation of optically active 3-substituted 1-benzylpiperidines based on the ring expansion of the 1-benzyl-2-(methylsulfonyloxymethyl)pyrrolidine 13 with various nucleophiles has been described. Synthesis of 4-amino-1,4,5-trideoxy-1,5-imino-D-ribitol 5, 1,4,5-trideoxy-4-fluoro-1,5-imino-D-ribitol 6 and 1,5-dideoxy-1,5-imino-D-ribitol 7 has also been achieved by a route which involves ring expansion of compound 13.

Fluorinated 1,5-Dideoxy-1,5-iminoalditols: Synthesis of 1,5,6-Trideoxy-6-fluoro-1,5-imino-D-glucitol (1,6-Dideoxy-6-fluoronojirimycin) and 1,4,5-Trideoxy-4-fluoro-1,5-imino-D-ribitol (1,2,5-Trideoxy-2-fluoro-1,5-imino-L-ribitol)

An efficient synthesis of 1,5,6-trideoxy-6-fluoro-1,5-imino-D-glucitol 13 from inexpensive L-sorbose by way of reductive amination of 12 is described.Synthesis of 1,4,5-trideoxy-4-fluoro-1,5-imino-D-ribitol (1,2,5-trideoxy-2-fluoro-1,5-imino-L-ribitol) 19