182156-06-5

Upstream product

• 182156-01-0 2-[1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-succinic acid 1-ethyl ester 
• 182156-03-2 2-[((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-hydroxy-succinic acid 1-ethyl ester 4-methyl ester 
• 182156-04-3 (4'R,5'S)-5'-Benzyloxymethyl-5-methoxycarbonylmethyl-2',2'-dimethyl-2-oxo-[4,4']bi[[1,3]dioxolanyl]-5-carboxylic acid ethyl ester 
• 182156-02-1 2-[1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-succinic acid 1-ethyl ester 4-methyl ester 
• 81028-12-8 (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 
• 65434-72-2 2-(triphenylphosphoranylidene)succinic acid 1-ethyl ester 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 182156-05-4 (Z)-2-[((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-but-2-enedioic acid 1-ethyl ester 4-methyl ester 

Downstream Products

• 182156-20-3 (E)-2-[((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-but-2-ene-1,4-diol 

Relevant academic research and scientific papers

Evaluation of furan photooxygenation as a device for construction of the zaragozic acid (squalestatin) core

A practical application of the photooxygenation chemistry of 3-substituted furans to construction of the zaragozic acid/squalestatin backbone is described. Although addition of 3-lithiofuran to the tartrate-derived aldehyde 7 proceeds without chelation control to give a 1:1 mixture of diastereomeric alcohols 8, it is demonstrated initially that ready conversion to the polyfunctional intermediate 16 is possible by sequential treatment of 9 with singlet oxygen, sodium borohydride, and triisopropylsilyl triflate. The actual enantiocontrolled route consisted of oxidation of 8 to the ketone and Wittig olefination of the latter in advance of asymmetric dihydroxylation with AD-mix-β. Cnce this series of transformations had been accomplished, formation of the target product 30 was realized by an entirely comparable photooxygenation.