tert-butyl((1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyloxy)dimethylsilane

Base Information

Chemical Name:tert-butyl((1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyloxy)dimethylsilane
CAS No.:1308247-24-6
Molecular Formula:C₂₃H₃₈O₅Si
Molecular Weight:422.637
Hs Code.:

Synonyms:tert-butyl((1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyloxy)dimethylsilane

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Chemical Property of tert-butyl((1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyloxy)dimethylsilane

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Technology Process of tert-butyl((1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyloxy)dimethylsilane

There total 7 articles about tert-butyl((1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyloxy)dimethylsilane 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: 84.0%

: 1308247-23-5
(1S,2R)-1-(tert-butyldimethylsilyloxy)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-2-ol

: 2746-25-0
p-Methoxybenzyl bromide

: 1308247-24-6
tert-butyl((1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyloxy)dimethylsilane

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1016/j.tet.2011.03.107

Reference yield:

: 879572-98-2
ethyl (2R,3R)-3,4-O-isopropylidene-2-[(tert-butyldimethylsilyl)oxy]-3,4-dihydroxybutanoate

: 1308247-24-6
tert-butyl((1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyloxy)dimethylsilane

Guidance literature:: Multi-step reaction with 5 steps

1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C

2: tetrahydrofuran / 3.33 h / -78 - 20 °C

3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3 h / 20 °C

4: potassium tri-sec-butyl-borohydride / tetrahydrofuran; toluene / 6 h / -78 - -40 °C

5: sodium hydride / tetrahydrofuran / 0 - 20 °C

With sodium hydride; diisobutylaluminium hydride; potassium tri-sec-butyl-borohydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1016/j.tet.2011.03.107

Reference yield:

: 1175536-43-2
(1S,2S)-1-(tert-butyldimethylsilyloxy)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-2-ol

: 1308247-24-6
tert-butyl((1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxybenzyloxy)but-3-enyloxy)dimethylsilane

Guidance literature:: Multi-step reaction with 3 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3 h / 20 °C

2: potassium tri-sec-butyl-borohydride / tetrahydrofuran; toluene / 6 h / -78 - -40 °C

3: sodium hydride / tetrahydrofuran / 0 - 20 °C

With sodium hydride; potassium tri-sec-butyl-borohydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; toluene;
DOI:10.1016/j.tet.2011.03.107