172877-80-4

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 172877-76-8 ((3aR,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxol-3a-yl)methanol 
• 172877-75-7 (3aS,7aR)-methyl 2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylate 
• 172877-72-4 (-)-(1S,6R)-methyl 1,6-dihydroxycyclohexa-2,4-dienecarboxylate 
• 32359-20-9 (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid 

Relevant academic research and scientific papers

Synthetic application of biotransformations: absolute stereochemistry and Diels-Alder reactions of the (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid from Pseudomonas putida

1,cis-2-Dihydroxycyclohexa-3,5-diene-1-carboxylic acid, 2, produced by Pseudomonas putide, U103, was shown via X-ray analysis of its p-bromobenzoylmethyl ester to have (1S 2R) absolute stereochemistry.The stereo- and regio-selectivity of a series of cycloadditions of the methyl ester 3 (R = Me) the methyl ester acetonide 5 and the hydroxymethylacetonide 6 (R = H) with singlet oxygen, 4-phenyl-4,5-dihydro-3H-1,2,4-triazole-3,5-dione, N-phenylmaleimide and nitrosobenzene have been established.The stereochemistry of the oxygen adduct 7 of 5 was unambiguously assigned by X-ray analysis of 7.The acetonides 5 and 6 (R = H) were attacked by the dienophiles anti to the acetonide group.The diol ester 3 underwent attack on the face syn to the diol groups.The regiochemistry of the addition of nitrosobenzene was predominantly with the N-phenyl group distal to the ester function in 3 and 5, but proximal to the hydroxymethyl group in 6 (R = H).