1476028-70-2

Upstream product

• 1476028-68-8 (3R,4S,5R)-ethyl 3,4-epoxy-5-hydroxycyclohex-1-ene-1-carboxylate 
• 1476028-67-7 (3S,4S,5R)-ethyl 3-chloro-4,5-bis(formyloxy)cyclohex-1-ene-1-carboxylate 
• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 

Downstream Products

• 1476028-71-3 (3S,4S,5S)-ethyl 5-azido-3,4-dihydroxycyclohex-1-ene-1-carboxylate 
• 1476028-73-5 (3S,4S,5S)-ethyl 5-azido-3-(tert-butyldiphenylsilyloxy)-4-hydroxycyclohex-1-enecarboxylate 
• 1476028-74-6 (3S,4S,5R)-ethyl 5-azido-3-(tert-butyldiphenylsilyloxy)-4-hydroxycyclohex-1-enecarboxylate 
• 1476028-75-7 (3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate 
• 1476028-76-8 (3S,4S,5S)-4-acetoxy-5-azido-3-(tert-butyldiphenylsilyloxy)cyclo-hex-1-enylmethyl acetate 
• 1476028-77-9 (1S,2S,3S,4S,5S)-2-acetoxy-1-azido-3-(tert-butyldiphenylsilyloxy)-4,5-dihydroxycyclohex-5-ylmethyl acetate 
• 1476028-78-0 (1R,2S,3S,4S,5S)-2-acetoxy-1-azido-3-(tert-butyldiphenylsilyloxy)-4,5-dihydroxycyclohex-5-ylmethyl acetate 
• 148347-73-3 (1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-1,2,3-triyl triacetate 
• 694527-30-5 1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-5-azido-1,2,3,4-cyclohexanetetrol 
• 1054636-37-1 (1S,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane 
• 1476028-79-1 (1R,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane 
• 83465-22-9 (1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane 
• 141042-85-5 (1S)-(1(OH),2,4/1,3,5)-5-Amino-1-C-(hydroxymethyl)-1,2,3,4-cyclohexanetetrol 

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