(4S,5S,7R,11R)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-11-(4-methoxybenzyloxy)-4,6,6-trimethylhexadeca-2,8-diynyl pivalate

Base Information

Chemical Name:(4S,5S,7R,11R)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-11-(4-methoxybenzyloxy)-4,6,6-trimethylhexadeca-2,8-diynyl pivalate
CAS No.:1554321-42-4
Molecular Formula:C₃₈H₆₂O₆Si
Molecular Weight:642.992
Hs Code.:

Synonyms:(4S,5S,7R,11R)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-11-(4-methoxybenzyloxy)-4,6,6-trimethylhexadeca-2,8-diynyl pivalate

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Chemical Property of (4S,5S,7R,11R)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-11-(4-methoxybenzyloxy)-4,6,6-trimethylhexadeca-2,8-diynyl pivalate

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Technology Process of (4S,5S,7R,11R)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-11-(4-methoxybenzyloxy)-4,6,6-trimethylhexadeca-2,8-diynyl pivalate

There total 10 articles about (4S,5S,7R,11R)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-11-(4-methoxybenzyloxy)-4,6,6-trimethylhexadeca-2,8-diynyl pivalate 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: 51.0%

: 1554321-35-5
(3R,7R)-3-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-ynal

: 1554321-42-4
(4S,5S,7R,11R)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-11-(4-methoxybenzyloxy)-4,6,6-trimethylhexadeca-2,8-diynyl pivalate

: 1554321-43-5
(4S,5R,7R,11R)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-11-(4-methoxybenzyloxy)-4,6,6-trimethylhexadeca-2,8-diynyl pivalate

Guidance literature:: (3R,7R)-3-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-ynal; With palladium diacetate; triphenylphosphine; In tetrahydrofuran; at -78 ℃; for 0.416667h; Inert atmosphere;

(3R,7R)-3-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,2-dimethyldodec-4-ynal; With diethylzinc; In tetrahydrofuran; hexane; at -78 - -20 ℃; for 37h;
DOI:10.1021/ol500050p

Reference yield:

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

: 1554321-42-4
(4S,5S,7R,11R)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-11-(4-methoxybenzyloxy)-4,6,6-trimethylhexadeca-2,8-diynyl pivalate

Guidance literature:: Multi-step reaction with 8 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

6.1: diisobutylaluminium hydride / toluene; hexane / 1 h / -78 °C / Inert atmosphere

7.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-tetramethyl-piperidine-N-oxyl / dichloromethane / 74 h / 20 °C

8.1: palladium diacetate; triphenylphosphine / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

8.2: 37 h / -78 - -20 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; (-)-N-methylephedrine; palladium diacetate; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; mineral oil;
DOI:10.1021/ol500050p

Reference yield:

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

: 1554321-42-4
(4S,5S,7R,11R)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-11-(4-methoxybenzyloxy)-4,6,6-trimethylhexadeca-2,8-diynyl pivalate

Guidance literature:: Multi-step reaction with 7 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

5.1: diisobutylaluminium hydride / toluene; hexane / 1 h / -78 °C / Inert atmosphere

6.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-tetramethyl-piperidine-N-oxyl / dichloromethane / 74 h / 20 °C

7.1: palladium diacetate; triphenylphosphine / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

7.2: 37 h / -78 - -20 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; (-)-N-methylephedrine; palladium diacetate; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/ol500050p