3971-46-8

Upstream product

• 67-56-1 methanol 
• 1949-89-9 2-deoxy-D-galactose 
• 61-58-5 2-deoxy-D-lyxo-hexopyranose 
• 23568-30-1 2-Deoxy-L-arabino-hexose 
• 20770-58-5 Acetic acid (1S,2S)-2,3-diacetoxy-1-((S)-1,2-diacetoxy-ethyl)-4-nitro-butyl ester 
• 87858-15-9 3,4,5,6-Tetra-O-acetyl-1,2-dideoxy-1-nitro-L-arabino-hexitol 
• 87858-14-8 3,4,5,6-Tetra-O-acetyl-1,2-dideoxy-1-nitro-L-arabino-hex-1-enitol 

Downstream Products

• 151130-22-2 methyl 3-O-benzyl-2-deoxy-β-D-lyxo-hexopyranoside 
• 151130-24-4 methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl-2-deoxy-β-D-lyxo-hexopyranoside 
• 151183-18-5 methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside 
• 151130-26-6 methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl-2-deoxy-4-O-methylsulfonyl-β-D-lyxo-hexoside 
• 19131-11-4 methyl-2,6-didesoxy-β-L-arabino-hexopyranoside 
• 19131-10-3 methyl-2,6-didesoxy-α-L-arabino-hexopyranoside 
• 87782-53-4 Methyl 2-deoxy-β-L-arabino-hexopyranoside 6-p-toluenesulfonate 
• 87782-52-3 Methyl 2-deoxy-α-L-arabino-hexopyranoside 6-p-toluenesulfonate 
• 18981-64-1 Methyl 3-azido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 
• 85439-70-9 methyl-3,4-anhydro-2,6-didesoxy-α-L-lyxo-hexopyranoside 
• 19129-68-1 Methyl 3-azido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 4-benzoate 
• 18981-62-9 methyl 3-azido-2,3,6-trideoxy-4-O-methanesulphonyl-α-L-arabino-hexopyranoside 
• 67758-43-4 Methyl 2,6-dideoxy-α-L-arabino-hexopyranoside 3,4-di-p-toluenesulfonate 
• 18981-61-8 Methyl 2,6-dideoxy-α-L-arabino-hexopyranoside 3-p-toluenesulfonate 

Relevant academic research and scientific papers

A Unified Strategy to Access 2- And 4-Deoxygenated Sugars Enabled by Manganese-Promoted 1,2-Radical Migration

The selective manipulation of carbohydrate scaffolds is challenging due to the presence of multiple, nearly chemically indistinguishable O-H and C-H bonds. As a result, protecting-group-based synthetic strategies are typically necessary for carbohydrate modification. Here we report a concise semisynthetic strategy to access diverse 2- and 4-deoxygenated carbohydrates without relying on the exhaustive use of protecting groups to achieve site-selective reaction outcomes. Our approach leverages a Mn2+-promoted redox isomerization step, which proceeds via sugar radical intermediates accessed by neutral hydrogen atom abstraction under visible light-mediated photoredox conditions. The resulting deoxyketopyranosides feature chemically distinguishable functional groups and are readily transformed into diverse carbohydrate structures. To showcase the versatility of this method, we report expedient syntheses of the rare sugars l-ristosamine, l-olivose, l-mycarose, and l-digitoxose from commercial l-rhamnose. The findings presented here validate the potential for radical intermediates to facilitate the selective transformation of carbohydrates and showcase the step and efficiency advantages attendant to synthetic strategies that minimize a reliance upon protecting groups.

SYNTHESIS OF METHYL 2,6-DIDEOXY-α-D-XYLO- AND α-D-LYXO-HEXOPYRANOSIDE

Synthesis of the title glycosides from methyl 3,4-anhydro-6-deoxy-α-D-galactopyranoside and 2-deoxy-D-lyxo-hexopyranose is described.