[2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methylethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-14-hydroxy-2,6-bis[(methoxymethyl)oxy]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-methylethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-14-hydroxy-2,6-bis[(methoxymethyl)oxy]icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan
CAS No.:1335112-89-4
Molecular Formula:C₅₂H₈₈O₁₀Si
Molecular Weight:901.35
Hs Code.:

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

There total 6 articles about [2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methylethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-14-hydroxy-2,6-bis[(methoxymethyl)oxy]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: 70.0%

: 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

: 1335112-89-4
[2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methylethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-14-hydroxy-2,6-bis[(methoxymethyl)oxy]icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1002/chem.201100675

Reference yield:

: [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

: 1335112-89-4
[2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methylethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-14-hydroxy-2,6-bis[(methoxymethyl)oxy]icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 1.25 h / -78 - 20 °C / Inert atmosphere

1.3: 16 h / 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / methanol / 1 h / 0 °C / Inert atmosphere

With tert.-butyl lithium; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; pentane;
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

: 1335112-89-4
[2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)]-4-(2-methoxycarbonyl-1-methylethyl-1-yl)-6-{12-(t-butyldimethylsilyloxy)-5,7,9,11,13,15,19-heptamethyl-14-hydroxy-2,6-bis[(methoxymethyl)oxy]icosa-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

Guidance literature:: Multi-step reaction with 5 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

5.1: toluene-4-sulfonic acid / methanol / 1 h / 0 °C / Inert atmosphere

With 1H-imidazole; bis(acetylacetonate)nickel(II); iodine; tert.-butyl lithium; toluene-4-sulfonic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; pentane; benzene;
DOI:10.1002/chem.201100675