(5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(4-methoxybenzyloxy)-6-(triethylsilyloxy)-3-(trimethylsilyloxy)deca-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-(4-methoxybenzyloxy)-6-(triethylsilyloxy)-3-(trimethylsilyloxy)deca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one
CAS No.:902782-23-4
Molecular Formula:C₅₀H₇₇NO₁₀Si₂
Molecular Weight:908.333
Hs Code.:

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

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

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

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

There total 9 articles about (5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(4-methoxybenzyloxy)-6-(triethylsilyloxy)-3-(trimethylsilyloxy)deca-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: 73.0%

: 902782-22-3
(5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-10-cyclohexyl-3-(2-hydroxyethyl)-4-(4-methoxybenzyloxy)-6-(triethylsilyloxy)-3-(trimethylsilyloxy)deca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one

: 129220-90-2
diallyl imidodicarbonate

: 902782-23-4
(5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(4-methoxybenzyloxy)-6-(triethylsilyloxy)-3-(trimethylsilyloxy)deca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at -78 - 0 ℃;
DOI:10.1002/anie.200600458

Reference yield:

: 902782-15-4
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

: 902782-23-4
(5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(4-methoxybenzyloxy)-6-(triethylsilyloxy)-3-(trimethylsilyloxy)deca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 10 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

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; 1,1-Dibromoethane; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triphenylphosphine; lithium bromide; zinc; copper(I) bromide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene; benzene;
DOI:10.1002/anie.200600458

Reference yield:

: 902782-16-5
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

: 902782-23-4
(5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(4-methoxybenzyloxy)-6-(triethylsilyloxy)-3-(trimethylsilyloxy)deca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / pyridinium p-toluenesulfonate / methanol; tetrahydrofuran / 20 °C

2: 94 percent / Ti(O-iPr)4 / benzene / 0.33 h / 80 °C

3: 88 percent / Bu₄NF / tetrahydrofuran / 0.83 h / 0 - 20 °C

4: 83 percent / Zn; dibromoethane; LiBr / CuBr / ethanol; tetrahydrofuran / 2 h / 80 °C

5: 85 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

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

7: 558 mg / pyridinium p-toluenesulfonate / methanol; tetrahydrofuran / 4 h / 0 °C

8: 73 percent / PPh₃; diisopropyl azodicarboxylate / toluene / -78 - 0 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; 1,1-Dibromoethane; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triphenylphosphine; lithium bromide; zinc; copper(I) bromide; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; benzene;
DOI:10.1002/anie.200600458