1476028-75-7

Upstream product

• 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 
• 108-24-7 acetic anhydride 
• 101769-63-5 (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 1476028-71-3 (3S,4S,5S)-ethyl 5-azido-3,4-dihydroxycyclohex-1-ene-1-carboxylate 
• 1476028-70-2 (3S,4R,5R)-5-methanesulfonyloxy-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid ethyl ester 

Downstream Products

• 1476028-77-9 (1S,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 
• 1054636-37-1 (1S,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 

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