(3S,7R,Z)-methyl 3-(tert-butyldimethylsilyloxy)-4-iodo-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-enoate

Base Information

Chemical Name:(3S,7R,Z)-methyl 3-(tert-butyldimethylsilyloxy)-4-iodo-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-enoate
CAS No.:1554321-27-5
Molecular Formula:C₂₉H₄₉IO₅Si
Molecular Weight:632.695
Hs Code.:

Synonyms:(3S,7R,Z)-methyl 3-(tert-butyldimethylsilyloxy)-4-iodo-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-enoate

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Chemical Property of (3S,7R,Z)-methyl 3-(tert-butyldimethylsilyloxy)-4-iodo-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-enoate

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Technology Process of (3S,7R,Z)-methyl 3-(tert-butyldimethylsilyloxy)-4-iodo-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-enoate

There total 9 articles about (3S,7R,Z)-methyl 3-(tert-butyldimethylsilyloxy)-4-iodo-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-enoate 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: 91.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 1554321-25-3
(3S,7R,Z)-methyl 3-hydroxy-4-iodo-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-enoate

: 1554321-27-5
(3S,7R,Z)-methyl 3-(tert-butyldimethylsilyloxy)-4-iodo-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-enoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 - 0 ℃; for 5h; Inert atmosphere;
DOI:10.1021/ol500050p

Reference yield:

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

: 1554321-27-5
(3S,7R,Z)-methyl 3-(tert-butyldimethylsilyloxy)-4-iodo-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-enoate

Guidance literature:: Multi-step reaction with 7 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: triethyl borane / toluene; hexane / 0.08 h / 20 °C / Inert atmosphere

5.2: air / 7.67 h / 20 °C

6.1: N-iodo-succinimide / dichloromethane / 30 h / 20 °C / Inert atmosphere; Darkness

7.1: 2,6-dimethylpyridine / dichloromethane / 5 h / -78 - 0 °C / Inert atmosphere

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

Reference yield:

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

: 1554321-27-5
(3S,7R,Z)-methyl 3-(tert-butyldimethylsilyloxy)-4-iodo-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-enoate

Guidance literature:: Multi-step reaction with 6 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: triethyl borane / toluene; hexane / 0.08 h / 20 °C / Inert atmosphere

4.2: air / 7.67 h / 20 °C

5.1: N-iodo-succinimide / dichloromethane / 30 h / 20 °C / Inert atmosphere; Darkness

6.1: 2,6-dimethylpyridine / dichloromethane / 5 h / -78 - 0 °C / Inert atmosphere

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