(5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(diallyloxyphosphinyl)-3,6-dihydroxydeca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one

Base Information

• Chemical Name: (5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(diallyloxyphosphinyl)-3,6-dihydroxydeca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one
• CAS No.: 902782-26-7
• Molecular Formula: C₃₉H₅₆NO₁₂P
• Molecular Weight: 761.847

Synonyms:(5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(diallyloxyphosphinyl)-3,6-dihydroxydeca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one

Chemical Property of (5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(diallyloxyphosphinyl)-3,6-dihydroxydeca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(diallyloxyphosphinyl)-3,6-dihydroxydeca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one

There total 13 articles about (5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(diallyloxyphosphinyl)-3,6-dihydroxydeca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one 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: 95.0%

(5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(diallyloxyphosphinyl)-6-(triethylsilyloxy)-3-(trimethylsilyloxy)deca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one (902782-25-6) → (5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(diallyloxyphosphinyl)-3,6-dihydroxydeca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one (902782-26-7)

Guidance literature:

With acetyl chloride; In tetrahydrofuran; methanol; dichloromethane; at 0 ℃; for 2.5h;

DOI:10.1002/anie.200600458

Reference yield:

ethyl (2R,3S,4E,6R,7R,9R,12Z)-9-(tert-butyldimethylsiloxy)-6-(2-(tert-butyldiphenylsiloxy)ethyl)-13-cyclohexyl-2-ethyl-7-(4-methoxybenzyloxy)-3,6-bis(triethylsiloxy)trideca-4,12-dien-10-ynethioate (902782-15-4) → (5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(diallyloxyphosphinyl)-3,6-dihydroxydeca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one (902782-26-7)

Guidance literature:

Multi-step reaction with 14 steps

1: diisobutylaluminium hydride / toluene; hexane / 0.5 h / -78 °C

2: 2.40 g / Bu₄NOH / tetrahydrofuran; methanol / 6 h / -18 °C

3: 86 percent / pyridinium p-toluenesulfonate / methanol; tetrahydrofuran / 20 °C

4: 94 percent / Ti(O-iPr)4 / benzene / 0.33 h / 80 °C

5: 88 percent / Bu₄NF / tetrahydrofuran / 0.83 h / 0 - 20 °C

6: 83 percent / Zn; dibromoethane; LiBr / CuBr / ethanol; tetrahydrofuran / 2 h / 80 °C

7: 85 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

8: 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

9: 558 mg / pyridinium p-toluenesulfonate / methanol; tetrahydrofuran / 4 h / 0 °C

10: 73 percent / PPh₃; diisopropyl azodicarboxylate / toluene / -78 - 0 °C

11: 85 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 30 h / 0 °C

12: 1H-tetrazole / CH₂Cl₂ / 0.5 h / 20 °C

13: 311 mg / H₂O₂ / CH₂Cl₂ / 2 h / 0 °C

14: 95 percent / AcCl / methanol; tetrahydrofuran; CH₂Cl₂ / 2.5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; 1H-tetrazole; titanium(IV) isopropylate; 1,1-Dibromoethane; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; dihydrogen peroxide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; acetyl chloride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium bromide; zinc; copper(I) bromide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; toluene; benzene;

DOI:10.1002/anie.200600458

Reference yield:

(2R,3S,4E,6R,7R,9R,12Z)-9-(tert-butyldimethylsiloxy)-6-[2-(tert-butyldiphenylsiloxy)ethyl]-13-cyclohexyl-2-ethyl-7-(4-methoxybenzyloxy)-3,6-bis(triethylsiloxy)trideca-4,12-dien-10-ynal (902782-38-1) → (5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(diallyloxyphosphinyl)-3,6-dihydroxydeca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one (902782-26-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 2.40 g / Bu₄NOH / tetrahydrofuran; methanol / 6 h / -18 °C

2: 86 percent / pyridinium p-toluenesulfonate / methanol; tetrahydrofuran / 20 °C

3: 94 percent / Ti(O-iPr)4 / benzene / 0.33 h / 80 °C

4: 88 percent / Bu₄NF / tetrahydrofuran / 0.83 h / 0 - 20 °C

5: 83 percent / Zn; dibromoethane; LiBr / CuBr / ethanol; tetrahydrofuran / 2 h / 80 °C

6: 85 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

7: 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

8: 558 mg / pyridinium p-toluenesulfonate / methanol; tetrahydrofuran / 4 h / 0 °C

9: 73 percent / PPh₃; diisopropyl azodicarboxylate / toluene / -78 - 0 °C

10: 85 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 30 h / 0 °C

11: 1H-tetrazole / CH₂Cl₂ / 0.5 h / 20 °C

12: 311 mg / H₂O₂ / CH₂Cl₂ / 2 h / 0 °C

13: 95 percent / AcCl / methanol; tetrahydrofuran; CH₂Cl₂ / 2.5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; 1H-tetrazole; titanium(IV) isopropylate; 1,1-Dibromoethane; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; dihydrogen peroxide; pyridinium p-toluenesulfonate; acetyl chloride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium bromide; zinc; copper(I) bromide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; benzene;

DOI:10.1002/anie.200600458

upstream raw materials:

(5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(diallyloxyphosphinyl)-6-(triethylsilyloxy)-3-(trimethylsilyloxy)deca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one

ethyl (2R,3S,4E,6R,7R,9R,12Z)-9-(tert-butyldimethylsiloxy)-6-(2-(tert-butyldiphenylsiloxy)ethyl)-13-cyclohexyl-2-ethyl-7-(4-methoxybenzyloxy)-3,6-bis(triethylsiloxy)trideca-4,12-dien-10-ynethioate

(2R,3S,4E,6R,7R,9R,12Z)-9-(tert-butyldimethylsiloxy)-6-[2-(tert-butyldiphenylsiloxy)ethyl]-13-cyclohexyl-2-ethyl-7-(4-methoxybenzyloxy)-3,6-bis(triethylsiloxy)trideca-4,12-dien-10-ynal

ethyl (2Z,4S,5S,6E,8R,9R,11R,14Z)-11-(tert-butyldimethylsiloxy)-8-[2-(tert-butyldiphenylsiloxy)ethyl]-15-cyclohexyl-4-ethyl-9-(4-methoxybenzyloxy)-5,8-bis(triethylsiloxy)pentadeca-2,6,14-trien-12-ynoate

Downstream raw materials:

(+)-phoslactomycin B

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