[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

Base Information

• Chemical Name: [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
• CAS No.: 1335112-81-6
• Molecular Formula: C₃₃H₅₁IO₈
• Molecular Weight: 702.668

Synonyms:

Chemical Property of [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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [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

There total 1 articles about [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 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:

(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) + C26H50O2Sn (1335112-78-1) + chloromethyl methyl ether (107-30-2) + diazomethyl-trimethyl-silane (18107-18-1) → [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)

Guidance literature:

C₂₆H₅₀O₂Sn; With n-butyllithium; In tetrahydrofuran; diethyl ether; at -40 ℃; for 0.833333h; Inert atmosphere;

(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; With 9-methoxy-9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; hexane; at -40 - 0 ℃; for 1h; Inert atmosphere;

chloromethyl methyl ether; diazomethyl-trimethyl-silane; Further stages;

DOI:10.1002/chem.201100675

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,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) → C52H88O10Si (1335113-13-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tert.-butyl lithium / diethyl ether; pentane / 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 methanol; diethyl ether; pentane;

DOI:10.1002/chem.201100675

upstream raw materials:

(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

chloromethyl methyl ether

diazomethyl-trimethyl-silane

Downstream raw materials:

[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

C₅₂H₈₈O₁₀Si

C₅₃H₈₉NO₁₁Si

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