(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

Base Information

• Chemical Name: (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
• CAS No.: 80102-63-2
• Molecular Formula: C₃₉H₅₇NO₉Si
• Molecular Weight: 711.968
• Mol file: 80102-63-2.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 14 articles about (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 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 15.0%

(Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-{(4S,6R)-2,2-dimethyl-6-[(Z)-2-nitro-3-(2-pentyl-[1,3]dioxolan-2-yl)-propenyl]-[1,3]dioxan-4-yl}-oct-5-enoic acid methyl ester → (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 (74595-20-3) + (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 (80102-63-2)

Guidance literature:

With hydrogenchloride; In methanol; water; for 2h; Ambient temperature;

DOI:10.1139/v81-394

Reference yield:

(Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-{(4S,6S)-2,2-dimethyl-6-[(E)-2-nitro-3-(2-pentyl-[1,3]dioxolan-2-yl)-propenyl]-[1,3]dioxan-4-yl}-oct-5-enoic acid methyl ester → (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 (80102-63-2)

Guidance literature:

With ammonium chloride; In methanol; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(00)78823-X

Reference yield:

1-nitro-octan-3-one ethylene ketal (74581-60-5) → (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 (80102-63-2)

Guidance literature:

Multi-step reaction with 4 steps

1: di-isopropylamine / dimethylformamide / 18 h

2: 4-Me₂N-pyridine

3: K₂CO₃, 18-crown-6 / benzene / 4 h / 75 °C

4: NH₄Cl / methanol / 2 h / 20 °C

With dmap; 18-crown-6 ether; potassium carbonate; ammonium chloride; diisopropylamine; In methanol; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)78823-X

upstream raw materials:

1-nitro-octan-3-one ethylene ketal

(Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-((3aR,5S,6aR)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-oct-5-enoic acid methyl ester

(Z)-(8R,9S,11R)-8-(tert-Butyl-diphenyl-silanyloxy)-12,12-bis-ethylsulfanyl-9,11-dihydroxy-dodec-5-enoic acid methyl ester

methyl 8R-tert-butyldiphenylsilyloxy-9S,11R-dihydroxy-9,11-O-isopropylidene-12-oxo-dodeca-5Z-enoate

Downstream raw materials:

(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

methyl 8R-tert-butyldiphenylsilyloxy-11R-hydroxy-15-oxo-9S,12S-oxyeicosa-5Z,13E-dienoate

methyl 8R-tert-butyldiphenylsilyloxy-11R-hydroxy-13-nitro-15-oxo-9S,12S-oxyeicosa-5Z-enoate

methyl 8R-tert-butyldiphenylsilyloxy-11R,15S-dihydroxy-9S,12S-oxyeicosa-5Z,13E-dienoate