1449491-92-2

Upstream product

• 1449491-88-6 p-methoxyphenyl 2,3-anhydro-α-D-allopyranoside 
• 1449491-90-0 p-methoxyphenyl 2,3-anhydro-6-O-(tert-butyldimethylsilyl)-4-O-methyl-α-D-allopyranoside 
• 1449491-91-1 p-methoxyphenyl 6-O-(tert-butyldimethylsilyl)-4-O-methyl-3-deoxy-3-azido-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 197449-36-8 p-methoxyphenyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 1449491-86-4 p-methoxyphenyl 2,3-anhydro-6-O-(tert-butyldimethylsilyl)-α-D-allopyranoside 
• 157430-16-5 C₁₉H₃₀O₅Si 

Relevant academic research and scientific papers

A new route toward 2-acetamido-4-O-methyl-2-deoxy-d-mannopyranose from a Ferrier derivative of tri-O-acetyl-d-glucal, which contributes to aldolase-catalyzed synthesis of laninamivir (CS-8958)

A new route toward 2-acetamido-4-O-methyl-2-deoxy-d-mannopyranose (4-O-methylManNAc), the chemo-enzymatic precursor of 7-O-methylsialic acid and laninamivir, was established. Known p-methoxyphenyl 6-O-(tert- butyldimethylsilyl)-2,3-dideoxy-α-d-erythro-hex-2-enopyranoside was the starting material, and it was derived via Ferrier reaction from tri-O-acetyl-d-glucal. The total yield was 43% over six steps from the starting material. As the key steps, Payne oxidation provided a syn-epoxy alcohol, and the inversion from an aziridine to an oxazoline proceeded stereoselectively. Although the ring opening reaction of the epoxide with an azide gave both the 2- and 3-azido regioisomers, they could be merged into the desired aziridine via independent routes.