110390-52-8

Upstream product

• 136340-68-6 (1'R,2'S,5'R)-menthyl (1S,2R,3S,4S,5S,6S)-5,6-dihydroxy-3-<(S)_S-2-pyridylsulphinyl>-7-oxabicyclo<2.2.1>heptane-2-carboxylate 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 
• 121467-52-5 (1R,2R,3S,4S)-3-((S)-Pyridine-2-sulfinyl)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 

Downstream Products

• 136340-70-0 (1'R,2'S,5'R)-menthyl (1S,4S,5S,6S)-5,6-(isopropylidenedioxy)-3-(2-pyridylthio)7-oxabicyclo<2.2.1>hept-2-ene-2-carboxylate 
• 136340-69-7 (1'R,2'S,5'R)-menthyl (1S,4S,5S,6S)-5,6-(isopropylidenedioxy)-3-oxo-7-oxabicyclo<2.2.1>heptane-2-carboxylate 
• 110390-53-9 (1S,2S,6S,7S,8R,9S)-4,4-Dimethyl-9-(pyridine-2-sulfonyl)-3,5,10-trioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 16755-07-0 showdomycin 
• 136340-71-1 (1'R,2'S,5'R)-menthyl (1R,5S,6S,7S)-6,7-(isopropylidenedioxy)-3-oxo-2,8-dioxabicyclo<3.2.1>octan-4-carboxylate 

Relevant academic research and scientific papers

New Approach to Sugar Derivatives by Pummerer Reactions of Optically Active Sulphoxide and Sulphide having a 7-Oxabicycloheptane Ring System

Pummerer reactions of 3-(2-pyridylsulphinyl)-7-oxabicycloheptane-2-carboxylate 3 and the corresponding sulphide 4, which were obtained by an asymmetric Diels-Alder reaction of the (S)S-3-(2-pyridylsulphinyl)acrylate 2 with high diastereoselectivity, gave the β-keto ester 5 and the vinyl sulphide 6 in 62 and 87percent yield, respectively.The keto ester 5 was transformed into the C(5)-branched-chain sugar derivative by successive Baeyer-Villiger oxidation and stereoselective cleavage of the resulting lactone 16.Dealkoxycarbonylation of the keto ester 5 afforded the 7-oxanorbornanone derivative 8.In addition, upon ozonolysis, the vinyl sulphide 6 was converted into the D-2,5-anhydroallose derivative 9.