(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

Base Information

• Chemical Name: (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
• CAS No.: 1460293-60-0
• Molecular Formula: C₃₉H₆₈O₆S₂Si
• Molecular Weight: 725.183
• Mol file: 1460293-60-0.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 6 articles about (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 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:

(S,E)-10-methyl-11-oxoundec-7-enyl pivalate (1460293-39-3) + (S)-(4-(1,3-dithian-2-yl)-3-((4-methoxybenzyl)oxy)butoxy)(tert-butyl)dimethylsilane → (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 (1460293-59-7) + (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 (1460293-60-0)

Guidance literature:

(S)-(4-(1,3-dithian-2-yl)-3-((4-methoxybenzyl)oxy)butoxy)(tert-butyl)dimethylsilane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -10 ℃; for 1h;

(S,E)-10-methyl-11-oxoundec-7-enyl pivalate; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Overall yield = 92%; Overall yield = 210 mg; diastereoselective reaction;

DOI:10.1039/c3ob41569d

Reference yield:

(4S)-4-((1,3-dithian-2-yl)methyl)-2-(4-methoxyphenyl)-1,3-dioxane (1460293-45-1) → (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 (1460293-59-7) + (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 (1460293-60-0)

Guidance literature:

Multi-step reaction with 3 steps

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

2.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

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

3.2: 2 h / -78 °C

With 1H-imidazole; n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1039/c3ob41569d

Reference yield:

(S)-4-(1,3-dithian-2-yl)-3-((4-methoxybenzyl)oxy)butan-1-ol (1460293-46-2) → (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 (1460293-59-7) + (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 (1460293-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

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

2.2: 2 h / -78 °C

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1039/c3ob41569d

upstream raw materials:

(S,E)-10-methyl-11-oxoundec-7-enyl pivalate

(2S,4S)-4-hydroxymethyl-2-(p-methoxymethyl)-1,3-dioxane

(4S)-4-(iodomethyl)-2-(4-methoxyphenyl)-1,3-dioxane

(4S)-4-((1,3-dithian-2-yl)methyl)-2-(4-methoxyphenyl)-1,3-dioxane