71204-40-5

Upstream product

• 100-39-0 benzyl bromide 
• 53626-10-1 methyl 6-deoxy-4-O-methyl-α-L-mannopyranoside 
• 74-88-4 methyl iodide 
• 53577-83-6 methyl endo-2,3-O-benzylidene-4-O-methyl-α-L-rhamnopyranoside 
• 71204-39-2 methyl 3-O-benzyl-6-deoxy-4-O-methyl-α-L-mannopyranoside 

Downstream Products

• 94958-32-4 tert-Butyl-((2S,3S,4R,5R,6S)-3,5-dimethoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yloxy)-dimethyl-silane 

Relevant academic research and scientific papers

Selective cleavage of methoxy protecting groups in carbohydrates

The selective cleavage of methoxy protecting groups next to hydroxy groups is achieved using a radical hydrogen abstraction reaction as the key step. Under the reaction conditions, the hydroxy group generates an alkoxyl radical that reacts with the sterically accessible adjacent methoxy group, which is transformed into an acetal. In the second step, the acetals are hydrolyzed to give alcohols or diols. A one-pot hydrogen abstraction-hydrolysis procedure was also developed. Good yields were usually achieved, and the mild conditions of this methodology were compatible with different functional groups and sensitive substrates such as carbohydrates.

Total synthesis of elfamycins: Aurodox and efrotomycin. 1. Strategy and construction of key intermediates

The strategy for the total synthesis of aurodox and efrotomycin and the construction of key intermediates IV-VIII are described.

SYNTHESIS OF L-NOGALOSE AND ITS ENANTIOMER

L-Nogalose (6-deoxy-3-C-methyl-2,3,4-tri-O-methyl-L-mannopyranose) and its enantiomer were synthesized via (a) introduction of the C-methyl branch by successive epoxidation and reduction of methyl 3,6-dideoxy-2,4-di-O-methyl-3-C-methylene-α-L-arabino-hexopyranoside, and (b) deoxygenation at C-6 of methyl 4,6-O-benzylidene-3-C-methyl-2-O-methyl-α-D-mannopyranoside, and O-methylation of the product.