(3R,7R)-methyl 3-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-ynoate

Base Information

Chemical Name:(3R,7R)-methyl 3-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-ynoate
CAS No.:1554321-31-1
Molecular Formula:C₂₉H₄₈O₅Si
Molecular Weight:504.783
Hs Code.:

Synonyms:(3R,7R)-methyl 3-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-ynoate

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Chemical Property of (3R,7R)-methyl 3-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-ynoate

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Technology Process of (3R,7R)-methyl 3-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-ynoate

There total 7 articles about (3R,7R)-methyl 3-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-ynoate 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: 97.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 1554321-21-9
(3R,7R)-methyl 3-hydroxy-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-ynoate

: 1554321-31-1
(3R,7R)-methyl 3-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-ynoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 - -30 ℃; for 2.5h;
DOI:10.1021/ol500050p

Reference yield:

: 80800-66-4,120925-79-3
(R)-2-hydroxyheptyl p-toluenesulfonate

: 1554321-31-1
(3R,7R)-methyl 3-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-ynoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / diethyl ether; mineral oil / 43 h / 0 - 20 °C / Inert atmosphere

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 151 h / 0 - 20 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / dichloromethane / 143 h / 20 °C / Inert atmosphere

4.1: zinc trifluoromethanesulfonate; (-)-N-methylephedrine; triethylamine / tetrahydrofuran / 0.35 h / 20 °C / Inert atmosphere

4.2: 48 h / 20 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / -78 - -30 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; (-)-N-methylephedrine; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; mineral oil;
DOI:10.1021/ol500050p

Reference yield:

: 110549-07-0
(R)-1,2-epoxyheptane

: 1554321-31-1
(3R,7R)-methyl 3-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-ynoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 151 h / 0 - 20 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / dichloromethane / 143 h / 20 °C / Inert atmosphere

3.1: zinc trifluoromethanesulfonate; (-)-N-methylephedrine; triethylamine / tetrahydrofuran / 0.35 h / 20 °C / Inert atmosphere

3.2: 48 h / 20 °C / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / -78 - -30 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; (-)-N-methylephedrine; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol500050p