(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

Base Information

Chemical Name:(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
CAS No.:1586033-53-5
Molecular Formula:C₄₃H₆₂O₆Si
Molecular Weight:703.047
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 13 articles about (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 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:

: 1571059-44-3
(S)-6-(4-methoxybenzyloxy)hex-1-en-3-ol

: 1586033-52-4
tert-butyl-((R)-1-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)octyloxy)diphenylsilane

: 1586033-53-5
(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

: 1586033-64-8
(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

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:

: 119649-45-5
4-(p-methoxybenzyloxy)butan-1-ol

: 1586033-53-5
(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

Guidance literature:: Multi-step reaction with 5 steps

1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

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

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

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

5: 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; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; toluene; 5: |Cross Metathesis;
DOI:10.1016/j.tet.2014.02.072

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 1586033-53-5
(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

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

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

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

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

6.1: 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 hydride; sodium carbonate; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; toluene; mineral oil; 6.1: |Cross Metathesis;
DOI:10.1016/j.tet.2014.02.072