694527-30-5

Upstream product

• 1476028-70-2 (3S,4R,5R)-5-methanesulfonyloxy-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid ethyl ester 
• 1476028-72-4 (3S,4R,5R)-5-azido-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid ethyl ester 
• 1476028-74-6 (3S,4S,5R)-ethyl 5-azido-3-(tert-butyldiphenylsilyloxy)-4-hydroxycyclohex-1-enecarboxylate 
• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 
• 1476028-76-8 (3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate 
• 108-24-7 acetic anhydride 
• 1476028-78-0 (1R,2S,3S,4S,5S)-2-acetoxy-1-azido-3-(tert-butyldiphenylsilyloxy)-4,5-dihydroxycyclohex-5-ylmethyl acetate 
• 1476028-67-7 (3S,4S,5R)-ethyl 3-chloro-4,5-bis(formyloxy)cyclohex-1-ene-1-carboxylate 
• 1476028-68-8 (3R,4S,5R)-ethyl 3,4-epoxy-5-hydroxycyclohex-1-ene-1-carboxylate 
• 1476028-69-9 (3R,4R,5R)-ethyl 3,4-epoxy-5-(methylsulfonyloxy)cyclohex-1-ene-1-carboxylate 
• 693245-43-1 (1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-9-tosyloxy-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecan-7-ol 
• 694527-29-2 1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4,5-tetra-O-acetyl-1,2,3,4,5-cyclohexanepentol 
• 693245-41-9 (1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecane-7,9-diol 
• 693245-37-3 (1S,3R,6S,8R,9S,10R)-3-phenyl-2,4-dioxabicyclo[4.4.0]decane-6,8,9,10-tetrol 

Downstream Products

• 141042-85-5 (1S)-(1(OH),2,4/1,3,5)-5-Amino-1-C-(hydroxymethyl)-1,2,3,4-cyclohexanetetrol 
• 1476028-79-1 (1R,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane 
• 183505-16-0 1L-(1,2,4/3,5)-5-acetamido-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-1,2,3,4-cyclohexanetetraol 

Relevant academic research and scientific papers

Total syntheses of (+)-valiolamine and (-)-1-epi-valiolamine from naturally abundant (-)-shikimic acid

Total syntheses of (+)-valiolamine (1) and (-)-1-epi-valiolamine (2) from the naturally abundant (-)-shikimic acid are described. Ethyl 3-epi-5-O-methylsulfonyl-shikimate (3), as the key common intermediate, was first synthesized in five steps in 74 % overall yield, and then converted into the targets 1 and 2 in seven steps in 48 and 41 % overall yield, respectively. Copyright

Convenient synthesis of (+)-valiolamine and (-)-1-epi-valiolamine from (-)-vibo-quercitol

The synthesis of (+)-valiolamine and (-)-1-epi-valiolamine using bioconversion of (-)-vibo-quercitol was investigated. The quercitols were separated and purified by combination of chromatography on ion-exchange-resin columns and recrystallization. Valiolamine was isolated from fermentation broth of antibiotic validamycins. The obtained crude ketone was subjected to C-C bond formation conditions in which diazomethane was considered adequate in polar and protic solvsnts.