200432-36-6

Upstream product

• 89-82-7 pulegone 
• 660849-38-7 (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (1R,4R,5R,7S,8S)-8-acetoxy-2-benzyl-4-(methoxymethoxy)-7-iodo-3-oxo-2-azabicyclo[2.2.2]octane-5-carboxylate 
• 660849-30-9 (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (1R,4R,5S,7R,8R)-8-acetoxy-2-benzyl-4-(methoxymethoxy)-3-oxo-7-[(trifluoromethyl)sulfonyloxy]-2-azabicyclo[2.2.2]octane-5-carboxylate 
• 108-24-7 acetic anhydride 
• 660849-34-3 (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (1R,4R,5S,7S,8R)-7,8-diacetoxy-2-benzyl-4-(methoxymethoxy)-3-oxo-2-azabicyclo[2.2.2]octane-5-carboxylate 
• 660849-39-8 (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (1R,4R,5S,8S)-8-acetoxy-2-benzyl-4-(methoxymethoxy)-3-oxo-2-azabicyclo[2.2.2]octane-5-carboxylate 
• 65253-04-5 (-)-8-phenylmenthol 

Downstream Products

• 217323-86-9 ({(1R,2S,5R)-5-methyl-2-[1-methyl-1-(4-nitrophenyl)ethyl]cyclohexyl}oxy)carbonylhydroxylamine 
• 186045-26-1 (-)-(1R,2S,5R)-5-methyl-2-[1-methyl-1-(4-nitrophenyl)ethyl]cyclohexanol 
• 445012-71-5 (2S,5S,1R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (3S)-4,4,4-trifluoro-3-(4-methoxyanilino)-butanoate 
• 445009-12-1 (+)-(2S,5S,1R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl (Z)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-butenoate 
• 217323-75-6 (1R,2S,5R)-5-methyl-2-[1-methyl-1-(4-nitrophenyl)ethyl]cyclohexyl acetate 

Relevant academic research and scientific papers

Probing the conformational changes in the enzymatic hydrolysis of 2-acetamido-2-deoxy-β-D-glucopyranosides

The isoquinuclidines 7 and 8 were synthesised and tested as inhibitors of hexosaminidases from jack beans and from bovine kidney. These isoquinuclidines mimick the 1,4β-conformer of a N-acetyl-glucosamine-derived β-D-glucopyranoside; they are c

Isoquinuclidine Mimics of β-D-Glucopyranosides: Differences and Similarities in the Mechanism of Action of some β-D-Glucosidases and a β-D-Mannosidase

The D-gluco-isoquinuclidines 3 and 4 were prepared and tested as inhibitors of the β-glucosidases from Caldocellum saccharolyticum and from sweet almonds; the results are compared to the inhibition of snail β-mannosidase by the D-manno-isoquinuclidines 1

Total synthesis of (-)-epibatidine using an asymmetric Diels-Alder reaction with a chiral n-acylnitroso dienophile

An asymmetric total synthesis of (-)-epibatidine (1), isolated from the skin of the Ecuadorian poison frog, Epipedobates tricolor, of the family Dendrobatidae, has been achieved by virtue of the development of asymmetric hereto Diels-Alder (D-A) cycloaddition with an N-acylnitroso dienophile bearing the optically active 8-arylmenthol as a chiral source. Thus, in situ oxidation of the hydroxamic acid ent-12f incorporating the (1S,2R,5S)-8-(2- naphthyl)menthyl auxiliary was performed using the Swern conditions to produce the acylnitroso dienophile, which reacted at once with 2-chloro-5- (1,5-cyclohexadienyl)pyridine (7) to provide the (1S,4R)-meta-aza cycloadduct 24 as a major diastereoisomer. The observed facial diastereoselectivity is consistent with a transition-state model with the naphthyl group in 'stacked' position and with the acylnitroso group in the s-cis conformation, wherein π attractive interaction between the naphthyl and nitrosocarbonyl groups may contribute to facial control. Compound 24 underwent hydrogenation followed by removal of the chiral auxiliary with LiH2NBH3 and reductive cleavage of the N-O bond with Mo(CO)6 to give the amino alcohol derivative 29, which was converted to (-)-epibatidine via bromination followed by cyclization.