129751-08-2

Upstream product

• 131759-58-5 4-amino-3-(phenylthio)-3-buten-2-one 
• 88-95-9 Phthaloyl dichloride 
• 98816-00-3 4-hydroxy-3-(phenylthio)-3-buten-2-one 
• 76511-78-9 4-(dimethylamino)-3-(phenylthio)-3-buten-2-one 
• 131759-57-4 4-ethoxy-3-(phenylthio)-3-buten-2-one 

Downstream Products

• 129751-13-9 Acetic acid (2R,3R,4R)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-ethoxy-6-methyl-5-phenylsulfanyl-3,4-dihydro-2H-pyran-3-yl ester 
• 129751-13-9 Acetic acid (2S,3S,4R)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-ethoxy-6-methyl-5-phenylsulfanyl-3,4-dihydro-2H-pyran-3-yl ester 

Relevant academic research and scientific papers

Inter- and Intramolecular Hetero-Diels-Alder Reactions, 37. Syntheses of the 3-Amino Sugar Glycosides rac-4-Deoxydaunosaminide, rac-4-Deoxyristosaminide, and rac-Acosaminide

The hetero-Diels-Alder reaction of the phenylthio-activated N-monoacyl- and N,N-diacyl-enamino ketones 8a-c containing a methyl group at position 2 of the oxadiene with the electron-rich dienophiles 9a-c yields the exo/endo adducts 10a-d and 11a-d in 82-95percent yield with the endo adducts as the main products.The enamino ketone 8d with a S-ethyl group at C-3 does not react.Hydrogenation of 11a with Raney nickel in THF leads to the desulfurized dihydropyran 12, whereas in MeOH gives stereoselectively the perhydrophthalimido derivative 13, which, after deprotection, yieldsthe β-methyl glycoside 14 of rac-4-deoxydaunosamine.Under similar conditions 10c is converted into the β-ethyl glycoside 15 of rac-N-benzoyl-4-deoxyristosamine.Stereoselective hydroboration of 12 affords 17 and subsequent cleavage of the protecting group leads to the β-methyl glycoside 18 or rac-acosamine.