(S,Z)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(4-methoxybenzyloxy)hex-1-en-3-ol

Base Information

• Chemical Name: (S,Z)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(4-methoxybenzyloxy)hex-1-en-3-ol
• CAS No.: 1586033-64-8
• Molecular Formula: C₄₃H₆₂O₆Si
• Molecular Weight: 703.047
• Mol file: 1586033-64-8.mol

Synonyms:(S,Z)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(4-methoxybenzyloxy)hex-1-en-3-ol

Chemical Property of (S,Z)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(4-methoxybenzyloxy)hex-1-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,Z)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(4-methoxybenzyloxy)hex-1-en-3-ol

There total 13 articles about (S,Z)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(4-methoxybenzyloxy)hex-1-en-3-ol 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)-6-(4-methoxybenzyloxy)hex-1-en-3-ol (1571059-44-3) + tert-butyl-((R)-1-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)octyloxy)diphenylsilane (1586033-52-4) → (S,E)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(4-methoxybenzyloxy)hex-1-en-3-ol (1586033-53-5) + (S,Z)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(4-methoxybenzyloxy)hex-1-en-3-ol (1586033-64-8)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In dichloromethane; for 24h; Overall yield = 65 %; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2014.02.072

Reference yield:

C9H18O2 (1586033-59-1) → (S,Z)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(4-methoxybenzyloxy)hex-1-en-3-ol (1586033-64-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: dmap; 1H-imidazole / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 12 h / 20 °C / Inert atmosphere

4.1: camphorsulphonic acid / dichloromethane / 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 2.5 h / -78 °C / Inert atmosphere

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

6.2: 1 h / 20 °C / Inert atmosphere

7.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Inert atmosphere; Reflux

With 1H-imidazole; dmap; osmium(VIII) oxide; Hoveyda-Grubbs catalyst second generation; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination / 6.1: |Wittig Olefination / 6.2: |Wittig Olefination / 7.1: |Cross Metathesis;

DOI:10.1016/j.tet.2014.02.072

Reference yield:

4-((4-methoxybenzyl)oxy)butanal (119649-27-3) → (S,Z)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(4-methoxybenzyloxy)hex-1-en-3-ol (1586033-64-8)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2: chlorodicarbonyl(1-(isopropylamino)-2,3,4,5-tetraphenylcyclopentadienyl) ruthenium (II); sodium carbonate; potassium tert-butylate / toluene / 8 h / 20 °C / Inert atmosphere; Enzymatic reaction

3: potassium carbonate / methanol / 1.5 h / 20 °C / Inert atmosphere

4: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Inert atmosphere; Reflux

With chlorodicarbonyl(1-(isopropylamino)-2,3,4,5-tetraphenylcyclopentadienyl) ruthenium (II); Hoveyda-Grubbs catalyst second generation; potassium tert-butylate; sodium carbonate; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; toluene; 4: |Cross Metathesis;

DOI:10.1016/j.tet.2014.02.072

upstream raw materials:

C₉H₁₈O₂

p-Methoxybenzyl bromide

4-(p-methoxybenzyloxy)butan-1-ol

4-((4-methoxybenzyl)oxy)butanal

Refernces