(R,E)-methyl 3-(2,3-bis(tert-butyldimethylsilyloxy)propoxy)-4-(4-methoxybenzyloxy)but-2-enoate

Base Information

Chemical Name:(R,E)-methyl 3-(2,3-bis(tert-butyldimethylsilyloxy)propoxy)-4-(4-methoxybenzyloxy)but-2-enoate
CAS No.:1426310-13-5
Molecular Formula:C₂₈H₅₀O₇Si₂
Molecular Weight:554.872
Hs Code.:

Synonyms:(R,E)-methyl 3-(2,3-bis(tert-butyldimethylsilyloxy)propoxy)-4-(4-methoxybenzyloxy)but-2-enoate

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Chemical Property of (R,E)-methyl 3-(2,3-bis(tert-butyldimethylsilyloxy)propoxy)-4-(4-methoxybenzyloxy)but-2-enoate

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Technology Process of (R,E)-methyl 3-(2,3-bis(tert-butyldimethylsilyloxy)propoxy)-4-(4-methoxybenzyloxy)but-2-enoate

There total 5 articles about (R,E)-methyl 3-(2,3-bis(tert-butyldimethylsilyloxy)propoxy)-4-(4-methoxybenzyloxy)but-2-enoate 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:

: 1426310-12-4
(S,E)-methyl 3-(2,3-dihydroxypropoxy)-4-(4-methoxybenzyloxy)but-2-enoate

: 69739-34-0
t-butyldimethylsiyl triflate

: 1426310-13-5
(R,E)-methyl 3-(2,3-bis(tert-butyldimethylsilyloxy)propoxy)-4-(4-methoxybenzyloxy)but-2-enoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -30 ℃; for 0.5h;
DOI:10.1021/ol4001894

Reference yield:

: 1426310-11-3
(R,E)-methyl 3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-4-(4-methoxybenzyloxy)but-2-enoate

: 1426310-13-5
(R,E)-methyl 3-(2,3-bis(tert-butyldimethylsilyloxy)propoxy)-4-(4-methoxybenzyloxy)but-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: hydrogenchloride; water / methanol / 4 h / 0 °C

2: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -30 °C

With 2,6-dimethylpyridine; hydrogenchloride; water; In methanol; dichloromethane;
DOI:10.1021/ol4001894

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 1426310-13-5
(R,E)-methyl 3-(2,3-bis(tert-butyldimethylsilyloxy)propoxy)-4-(4-methoxybenzyloxy)but-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C

1.2: 22 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 1 h / -78 - 20 °C

3.1: trimethylphosphane / tetrahydrofuran; dichloromethane / 1 h / 0 °C

4.1: hydrogenchloride; water / methanol / 4 h / 0 °C

5.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -30 °C

With 2,6-dimethylpyridine; hydrogenchloride; n-butyllithium; water; sodium hydride; trimethylphosphane; In tetrahydrofuran; methanol; hexane; dichloromethane; mineral oil;
DOI:10.1021/ol4001894