175981-99-4

Upstream product

• 591-51-5 phenyllithium 
• 1615225-40-5 (2R,3S,4R,5S,6S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-nitro-6-phenyltetrahydro-2H-pyran 
• 117136-22-8 3,4,6-tri-O-benzyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose 
• 100-58-3 phenylmagnesium bromide 
• 175981-95-0 (3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran-2-ol 
• 160701-84-8 (3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 108-24-7 acetic anhydride 
• 175982-00-0 (2S,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran 

Downstream Products

• 176198-89-3 N-((2S,3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenyl-tetrahydro-pyran-3-yl)-acetamide 

Relevant academic research and scientific papers

Stereoselective access to β-C-glycosamines by nitro-Michael addition of organolithium reagents

The nitro-Michael addition of organolithium species to 2-nitroglycal derivatives was investigated. This methodology affords straightforward and stereoselective access to C-nitroglycosides, which are excellent precursors to C-N-acetylglycosamines. The corresponding products bearing an aromatic, heteroaromatic, alkynyl, alkenyl, or alkyl moiety were isolated in good yields with excellent selectivities. The β isomer was isolated as a single stereoisomer in most cases, and the structure was clearly elucidated by NMR spectroscopy experiments. Copyright

Stereocontrolled synthesis of 2-azido and 2-N-acetylamino-2-deoxy-β-D-C-glycosides from the corresponding lactones

The reaction of perbenzylated 2-azido-2-deoxy-D-hexono1,5-lactones with organometallic reagents followed by reduction provides a new stereocontrolled synthesis of 2-azido-2-deoxy-β-D-C-glycosides, which can be efficiently transformed into 2-N-acetylamino-