1393085-98-7

Upstream product

• 7322-31-8 β-D-mannose 
• 96-22-0 pentan-3-one 
• 1393085-97-6 2,3:5,6-di-O-isopentylidene-α-D-mannofuranose 
• 100-44-7 benzyl chloride 

Downstream Products

• 1393086-00-4 C₁₇H₂₂O₅ 
• 204255-11-8 oseltamivir phosphate 
• 196618-13-0 oseltamivir 
• 204255-06-1 oseltamivir 
• 1132659-99-4 (3R,4S,5R)-4-acetylamino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 1149345-89-0 ethyl (3R,4R,5R)-4-acetamido-3-(1-ethyl-propoxy)-5-hydroxy-cyclohex-1-ene-1-carboxylate 
• 1408058-34-3 C₁₉H₂₇NO₅ 
• 1408058-32-1 C₁₉H₂₉NO₅ 
• 1408058-31-0 C₂₅H₄₃NO₅Si 
• 1408058-30-9 C₂₃H₃₉N₃O₄Si 
• 1408058-28-5 C₁₇H₂₆O₅ 

Relevant academic research and scientific papers

An efficient synthesis and regioselective hydrogenolysis of dioxolane-type of carbohydrates

Carbohydrates, inexpensive chiral sources, are very useful for many syntheses of chiral bioactive compounds. We have chosen to synthesize benzyl α-d-mannofuranosides and d-lyxofuranosides with dioxolane-type, 2,3-O-isopentylidene and 2,3-O-benzylidene acetals from d-mannose. Interestingly, we have discovered new knowledge about the cleavage of dioxolane-type using two catalysts, Cu(OTf)2/BH3·THF and TiCl4/Et3SiH. The results showed that the regioselectivity of the benzylidene acetal ring opening was affected by the adjacent hydroxy (OH) group and was not directed by the stereochemistry of the acetal center. The substrates containing OH groups at position 5 can be cleaved by Cu(OTf)2/BH3·THF in tetrahydrofuran to exclusively provide the 2-O-benzyl-3-hydroxy compounds. When the substrates bore the OH group at position 6, using TiCl4/Et3SiH in dichloromethane gave a similar pattern. If the substrates lacked the OH group at position 5 or 6, the reactions did not proceed or gave low selectivity. Our discovery is very useful for dioxolane-type ring opening of carbohydrate synthesis.

A concise and practical synthesis of oseltamivir phosphate(Tamiflu) from d-mannose

A short and practical synthesis of oseltamivir phosphate was accomplished in 11 steps from inexpensive and abundant starting material, d-mannose. This synthetic route featured an intramolecular Horner-Wadsworth-Emmons reaction as the key step to furnish the cyclohexene ring product. The hydroxyl group was converted stereo specifically into an amino group by oxidation to the ketone and reductive amination whereas the second amino group was introduced by azide substitution of a hydroxyl group. This synthesis provided an economical and practical alternative for the synthesis of Tamiflu.

A new and efficient asymmetric synthesis of oseltamivir phosphate(Tamiflu) from D-mannose

Oseltamivir phosphate (Tamiflu) was synthesized from D-mannose through a short and practical synthetic route. A unique feature of the route is that the bulky 3-pentyloxy group and adjacent acetamide of Tamiflu were introduced at an early stage of the synthesis by copper-catalyzed regioselective ringopening of the 2,3-pentylidene ketal of D-lyxofuranoside. The D-lyxofuranoside ethylphosphonate precursor was then cyclized via an intramolecular Horner-Wadsworth-Emmons reaction to furnish the Tamiflu skeleton.