[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)-9-ipropyl-5,7,11,13,15-pentamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)-nonadeca-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)-9-ipropyl-5,7,11,13,15-pentamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)-nonadeca-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan
• CAS No.: 1335112-82-7
• Molecular Formula: C₅₈H₁₀₂O₁₀Si₂
• Molecular Weight: 1015.61

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)-9-ipropyl-5,7,11,13,15-pentamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)-nonadeca-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

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)-9-ipropyl-5,7,11,13,15-pentamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)-nonadeca-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

Chemical Property:

Purity/Quality:

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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)-9-ipropyl-5,7,11,13,15-pentamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)-nonadeca-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

There total 3 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)-9-ipropyl-5,7,11,13,15-pentamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)-nonadeca-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: 10.0%

(Z)-(5S,6S,7R,8S,9R)-8-(tert-butyl-dimethyl-silanyloxy)-10-iodo-5,7,9-trimethyl-6-triethylsilanyloxy-deca-1,3-diene + [2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z)]-4-[2-methoxycarbonyl-1-methyl ethyl-1-yl]-6-{9-iodo-2,6-bis[(methoxymethyl)oxy]-5,7,10-trimethyl-undeca-3,8-dien-3-yn-1-yl}-5-methyl-2-phenyl-1,3-dioxinan (1335112-81-6) → [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)-9-ipropyl-5,7,11,13,15-pentamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)-nonadeca-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan (1335112-82-7)

Guidance literature:

(Z)-(5S,6S,7R,8S,9R)-8-(tert-butyl-dimethyl-silanyloxy)-10-iodo-5,7,9-trimethyl-6-triethylsilanyloxy-deca-1,3-diene; With tert.-butyl lithium; In diethyl ether; pentane; Inert atmosphere;

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

[2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z)]-4-[2-methoxycarbonyl-1-methyl ethyl-1-yl]-6-{9-iodo-2,6-bis[(methoxymethyl)oxy]-5,7,10-trimethyl-undeca-3,8-dien-3-yn-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:

(2S,4S,5S,6R)-2-{6-[2-(tert-butyldimethylsilyloxy)-1-methyl-ethyl]-5-methyl-2-phenyl-1,3-dioxinan-4-yl}-N-methoxy-N-methyl-acetamide (939795-42-3) → [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)-9-ipropyl-5,7,11,13,15-pentamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)-nonadeca-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan (1335112-82-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.83 h / -40 °C / Inert atmosphere

1.2: 1 h / -40 - 0 °C / Inert atmosphere

2.1: tert.-butyl lithium / diethyl ether; pentane / Inert atmosphere

2.2: 1.25 h / -78 - 20 °C / Inert atmosphere

2.3: 16 h / 20 °C / Inert atmosphere

With n-butyllithium; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; pentane;

DOI:10.1002/chem.201100675

Reference yield:

C26H50O2Sn (1335112-78-1) → [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)-9-ipropyl-5,7,11,13,15-pentamethyl-2,6-bis[(methoxymethyl)oxy]-14-(triethylsilyloxy)-nonadeca-3,8,16,18-tetraen-1-yl}-5-methyl-2-phenyl-1,3-dioxinan (1335112-82-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.83 h / -40 °C / Inert atmosphere

1.2: 1 h / -40 - 0 °C / Inert atmosphere

2.1: tert.-butyl lithium / diethyl ether; pentane / Inert atmosphere

2.2: 1.25 h / -78 - 20 °C / Inert atmosphere

2.3: 16 h / 20 °C / Inert atmosphere

With n-butyllithium; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; pentane;

DOI:10.1002/chem.201100675

upstream raw materials:

[2S,4R(1R),5S,6S(2S,3Z,5S,6S,7S,8Z)]-4-[2-methoxycarbonyl-1-methyl ethyl-1-yl]-6-{9-iodo-2,6-bis[(methoxymethyl)oxy]-5,7,10-trimethyl-undeca-3,8-dien-3-yn-1-yl}-5-methyl-2-phenyl-1,3-dioxinan

(2S,4S,5S,6R)-2-{6-[2-(tert-butyldimethylsilyloxy)-1-methyl-ethyl]-5-methyl-2-phenyl-1,3-dioxinan-4-yl}-N-methoxy-N-methyl-acetamide

C₂₆H₅₀O₂Sn

Downstream raw materials:

C₅₂H₈₈O₁₀Si

C₅₃H₈₉NO₁₁Si

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