74581-59-2

Upstream product

• 3253-75-6 1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside 
• 75685-18-6 methyl 8R-tert-butyldiphenylsilyloxy-9R,11R-dihydroxy-9,11-O-isopropylidene-12,12-di(ethylthio)dodeca-5Z-enoate 
• 74595-17-8 (Z)-(8R,9R,11R)-8-(tert-Butyl-diphenyl-silanyloxy)-12,12-bis-ethylsulfanyl-9,11-dihydroxy-dodec-5-enoic acid methyl ester 
• 75685-17-5 (Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-((3aR,5R,6aR)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-oct-5-enoic acid methyl ester 
• 75685-15-3 (R)-8-((3aR,5R,6aR)-2,2-Dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-8-hydroxy-oct-5-ynoic acid methyl ester 
• 75685-16-4 (Z)-(R)-8-((3aR,5R,6aR)-2,2-Dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-8-hydroxy-oct-5-enoic acid methyl ester 
• 75646-89-8 (R)-8-((3aR,5R,6aR)-2,2-Dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-8-hydroxy-oct-5-ynoic acid 
• 2457-93-4 (3aR,5R,6aR)-2,2-dimethyl-5-((S)-oxiran-2-yl)tetrahydrofuro[3,2-d][1,3]dioxole 
• 75646-85-4 3-p-toluenesulphonate of 1,2-O-isopropylidene-5,6-O-methoxymethylidene-α-D-glucofuranose 
• 75646-86-5 1,2-O-isopropylidene-5,6-O-methoxymethylidene-3-deoxy-D-erythro-3,4-hexofuranoside 
• 76119-18-1 1,2-O-isopropylidene-5,6-O-methoxymethylidene-3-deoxy-α-D-xylohexofuranose 
• 2946-01-2 (3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate 
• 53293-00-8 hex-5-ynoic acid 
• 4005-46-3 (1R)-1-[(3aR,5R,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol 

Downstream Products

• 93547-88-7 t-butyl diphenylsilanol 
• 75879-51-5 methyl 8R-tert-butyldiphenylsilyloxy-9S,11R-dihydroxy-9,11-O-isopropylidene-eicosa-5Z,12E,14Z-trienoate 
• 75646-93-4 methyl 8R-tert-butyldimethylsilyloxy-9R,11R-dihydroxy-9,11-O-isopropylidene-eicosa-5Z,12E,14-trienoate 
• 75646-92-3 methyl 8R-tert-butyldiphenylsilyloxy-9R,11R-dihydroxy-9,11-O-isopropylidene-14-oxo-tetradeca-5Z,12E-dienoate 
• 75879-50-4 methyl 8R-tert-butyldiphenylsilyloxy-9S,11R-dihydroxy-9,11-O-isopropylidene-14-oxo-tetradeca-5Z,12E-dienoate 
• 74581-62-7 (Z)-(R)-8-{(4S,6S)-6-[1-Acetoxy-2-nitro-3-(2-pentyl-[1,3]dioxolan-2-yl)-propyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-8-(tert-butyl-diphenyl-silanyloxy)-oct-5-enoic acid methyl ester 
• 80102-63-2 (5Z,12E)-(8R,9S,11S)-8-(tert-Butyl-diphenyl-silanyloxy)-9,11-dihydroxy-13-nitro-14-(2-pentyl-[1,3]dioxolan-2-yl)-tetradeca-5,12-dienoic acid methyl ester 
• 74581-67-2 (Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4R,5S)-4-hydroxy-5-((E)-3-hydroxy-oct-1-enyl)-tetrahydro-furan-2-yl]-oct-5-enoic acid methyl ester 
• 80126-60-9 methyl 8R-tert-butyldiphenylsilyloxy-11R,15S-dihydroxy-9S,12S-oxyeicosa-5Z,13E-dienoate 
• 80126-61-0 methyl 8R-tert-butyldiphenylsilyloxy-11R,15R-dihydroxy-9S,12S-oxyeicosa-5Z,13E-dienoate 
• 74581-62-7 (Z)-(R)-8-{(4S,6R)-6-[1-Acetoxy-2-nitro-3-(2-pentyl-[1,3]dioxolan-2-yl)-propyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-8-(tert-butyl-diphenyl-silanyloxy)-oct-5-enoic acid methyl ester 
• 80102-63-2 (5Z,12Z)-(8R,9S,11R)-8-(tert-Butyl-diphenyl-silanyloxy)-9,11-dihydroxy-13-nitro-14-(2-pentyl-[1,3]dioxolan-2-yl)-tetradeca-5,12-dienoic acid methyl ester 
• 80126-59-6 methyl 11R-acetoxy-8R-tert-butyldiphenylsilyloxy-15-oxo-9S,12S-oxyeicosa-5Z,13E-dienoate 
• 74595-20-3 (Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-{(2S,4R)-4-hydroxy-5-[1-nitro-2-(2-pentyl-[1,3]dioxolan-2-yl)-ethyl]-tetrahydro-furan-2-yl}-oct-5-enoic acid methyl ester 

Relevant academic research and scientific papers

Oxidation products of arachidonic acid. III. The synthesis of methyl 8R,9R,11R-, 8S,9R,11R-, and 8S,9S,11R-triacetoxyeicosa-5Z,12E,14Z-trienoate

A stereospecific synthesis of the title compounds, starting from readily available glucose derivatives, is described, and methods for differentiating them and the already reported 8R,9S,11R-eicosatrienoate are discussed.

Oxidation products of arachidonic acid II. The synthesis of methyl 8R,9S,11R-trihydroxy-5Z,12E,14Z-eicosatrienoate

A stereospecific total synthesis of the title compound, 37, starting from diacetone glucose (9), is described.Key intermediates in the synthesis are 3-deoxy-5,6-anhydro-1,2-O-isopropylidene-glucofuranose (15), obtained in 50percent yield fom 9, and methyl

Oxidation products of arachidonic acid I. The synthesis of methyl 8R, 11R, 15-trihydroxy-9S, 12-oxyeicosa-5Z, 13E-dienoate (19)

Diacetone glucose was converted in high yield to 3-deoxy-5-6-anhydro-1,2-0-isopropylidene-D-glucofuranose(3), which was transformed to title compound.3 Its mass spectrum confirms the structure of a naturally occurring oxidation product of arach