(10S,11R,14S,E)-16-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-((4-methoxybenzyl)oxy)-10-methyl-12-oxohexadec-7-en-1-yl pivalate

Base Information

Chemical Name:(10S,11R,14S,E)-16-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-((4-methoxybenzyl)oxy)-10-methyl-12-oxohexadec-7-en-1-yl pivalate
CAS No.:1460293-48-4
Molecular Formula:C₃₆H₆₂O₇Si
Molecular Weight:634.97
Hs Code.:

Synonyms:(10S,11R,14S,E)-16-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-((4-methoxybenzyl)oxy)-10-methyl-12-oxohexadec-7-en-1-yl pivalate

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Chemical Property of (10S,11R,14S,E)-16-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-((4-methoxybenzyl)oxy)-10-methyl-12-oxohexadec-7-en-1-yl pivalate

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Technology Process of (10S,11R,14S,E)-16-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-((4-methoxybenzyl)oxy)-10-methyl-12-oxohexadec-7-en-1-yl pivalate

There total 8 articles about (10S,11R,14S,E)-16-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-((4-methoxybenzyl)oxy)-10-methyl-12-oxohexadec-7-en-1-yl 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: 75.0%

: 1460293-59-7
(10S,E)-11-(2-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-1,3-dithian-2-yl)-11-hydroxy-10-methylundec-7-en-1-yl pivalate

: 1460293-48-4
(10S,11R,14S,E)-16-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-((4-methoxybenzyl)oxy)-10-methyl-12-oxohexadec-7-en-1-yl pivalate

Guidance literature:: With bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.0166667h;
DOI:10.1039/c3ob41569d

Reference yield:

: 1460293-39-3
(S,E)-10-methyl-11-oxoundec-7-enyl pivalate

: 1460293-48-4
(10S,11R,14S,E)-16-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-((4-methoxybenzyl)oxy)-10-methyl-12-oxohexadec-7-en-1-yl pivalate

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 - -10 °C

1.2: 2 h / -78 °C

2.1: bis-[(trifluoroacetoxy)iodo]benzene / tetrahydrofuran; methanol; water / 0.02 h / 20 °C

With n-butyllithium; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; hexane; water;
DOI:10.1039/c3ob41569d

Reference yield:

: 103708-37-8
(2S,4S)-4-hydroxymethyl-2-(p-methoxymethyl)-1,3-dioxane

: 1460293-48-4
(10S,11R,14S,E)-16-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-((4-methoxybenzyl)oxy)-10-methyl-12-oxohexadec-7-en-1-yl pivalate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 12 h / 0 - 20 °C

2.1: tert.-butyl lithium; N,N,N,N,N,N-hexamethylphosphoric triamide / hexane; tetrahydrofuran / 1.5 h / -30 °C

2.2: 0.75 h / -78 °C

3.1: diisobutylaluminium hydride / toluene; dichloromethane / 4 h / -78 - 20 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

5.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 - -10 °C

5.2: 2 h / -78 °C

6.1: bis-[(trifluoroacetoxy)iodo]benzene / tetrahydrofuran; methanol; water / 0.02 h / 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; iodine; tert.-butyl lithium; diisobutylaluminium hydride; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1039/c3ob41569d