1149345-82-3

Upstream product

• 1149345-81-2 ethyl (3R,4R,5R)-5-O-benzoyl-shikimate 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 1149345-83-4 ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate 
• 1224733-28-1 ethyl (3S,4S,5R)-3-acetoxy-5-benzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate 
• 1224733-30-5 ethyl (3S,4S,5R)-3,5-dibenzoyloxy-4-(methylsulfonyloxy)cyclohex-1-enecarboxylate 

Relevant academic research and scientific papers

Inversion of secondary chiral alcohols in toluene with the tunable complex of R3N{single bond}R′COOH

The SN2 reaction of enantiomerically pure sulfonates with the tunable complex of R3N-R′COOH in toluene has been extensively studied. It was revealed that the molar ratio of the tertiary amines and carboxylic acids in the complex of R3NR′COOH is crucial for the SN2 reaction, and should be tuned for each sulfonate to give the best yield. Fifteen sulfonates 1 and 3-13 (Scheme 2) were prepared and transformed into 22 corresponding inverted esters 2 and 14-24 (Scheme 2) in good to high yields.

A novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (-)-shikimic acid

Oseltamivir phosphate 1 was synthesized starting from a readily available acetonide, that is, ethyl (3R,4S,5R)-3,4-O-isopropylidene shikimate 2, through a new route via 11 steps and in 44% overall yield. The synthesis described in this article is characterized by two particular steps: the highly regioselective and stereoselective facile nucleophilic replacement of an OMs by an N3 group at the C-3 position of ethyl (3R,4S,5R)-3,4-O-bismethanesulfonyl-5-O-benzoyl shikimate 5, and the mild ring-opening of an aziridine with 3-pentanol at the C-1 position of ethyl (1S,5R,6S)-7-acetyl-5-benzoyloxy-7-azabicyclo[4,1,0]hept-2-ene-3-carboxylate 8.