[2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methyl ethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

Base Information

Chemical Name:[2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methyl ethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan
CAS No.:1335112-71-4
Molecular Formula:C₅₈H₁₀₂O₁₀Si₂
Molecular Weight:1015.61
Hs Code.:

[2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methyl ethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

Synonyms:[2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methyl ethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

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Chemical Property of [2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methyl ethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

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Technology Process of [2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methyl ethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

There total 4 articles about [2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methyl ethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan 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: 51.0%

: [2S,4R(1R),5S,6S(2S,3Z,5S,6R,7S,8Z)]-4-(2-methoxycarbonyl-1-methyl-ethyl-1-yl)-6-{5,7-dimethyl-9-iodo-2,6-bis[(methoxymethyl)oxy]-deca-3,8-dien-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

: 1335112-70-3
(2Z,4Z,6S,7S,8R,9S,10R)-9-(t-butyldimethylsilyloxy)-11-iodo-7-(triethylsilyloxy)-1,5,7,9-tetramethyl undeca-2,4-diene

: 1335112-71-4
[2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methyl ethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

Guidance literature:: (2Z,4Z,6S,7S,8R,9S,10R)-9-(t-butyldimethylsilyloxy)-11-iodo-7-(triethylsilyloxy)-1,5,7,9-tetramethyl undeca-2,4-diene; With tert.-butyl lithium; In tetrahydrofuran; diethyl ether; pentane; for 0.0333333h; Inert atmosphere;

With 9-methoxy-9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; diethyl ether; hexane; pentane; at -78 - 20 ℃; for 1.25h; Inert atmosphere;

[2S,4R(1R),5S,6S(2S,3Z,5S,6R,7S,8Z)]-4-(2-methoxycarbonyl-1-methyl-ethyl-1-yl)-6-{5,7-dimethyl-9-iodo-2,6-bis[(methoxymethyl)oxy]-deca-3,8-dien-1-yl}-5-methyl-2-phenyl-1,3-dioxinan; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; caesium carbonate; In water; N,N-dimethyl-formamide; at 20 ℃; for 16h; Inert atmosphere;
DOI:10.1002/chem.201100675

Reference yield:

: (1Z,3S,4S,5R,6R,7S)-6-(tert-butyldimethylsilyloxy)-1-[(N,N-diisopropyl)-carbamoyloxy]-8-(4-methoxybenzyloxy)-4-(triethylsilyloxy)-3,5,7-trimethyloct-1-ene

: 1335112-71-4
[2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methyl ethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

Guidance literature:: Multi-step reaction with 4 steps

1.1: bis(acetylacetonate)nickel(II) / tetrahydrofuran; diethyl ether / 16 h / 0 °C / Inert atmosphere

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3.66 h / 0 - 20 °C / Inert atmosphere

3.1: 1H-imidazole; iodine; triphenylphosphine / diethyl ether; benzene / 2 h / 0 - 20 °C / Inert atmosphere

4.1: tert.-butyl lithium / tetrahydrofuran; diethyl ether; pentane / 0.03 h / Inert atmosphere

4.2: 1.25 h / -78 - 20 °C / Inert atmosphere

4.3: 16 h / 20 °C / Inert atmosphere

With 1H-imidazole; bis(acetylacetonate)nickel(II); iodine; tert.-butyl lithium; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; pentane; benzene;
DOI:10.1002/chem.201100675

Reference yield:

: 1335112-67-8
(2Z,4Z,6S,7S,8R,9R,10S)-9-(t-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-7-(triethylsilyloxy)-1,5,7,9-tetramethyl undeca-2,4-diene

: 1335112-71-4
[2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methyl ethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3.66 h / 0 - 20 °C / Inert atmosphere

2.1: 1H-imidazole; iodine; triphenylphosphine / diethyl ether; benzene / 2 h / 0 - 20 °C / Inert atmosphere

3.1: tert.-butyl lithium / tetrahydrofuran; diethyl ether; pentane / 0.03 h / Inert atmosphere

3.2: 1.25 h / -78 - 20 °C / Inert atmosphere

3.3: 16 h / 20 °C / Inert atmosphere

With 1H-imidazole; iodine; tert.-butyl lithium; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; pentane; benzene;
DOI:10.1002/chem.201100675