(2R,3S)-3-(tert-butoxycarbonyl)-5-(4-methoxybenzyl)oxy-2-vinyl-1,3-pentanediol

Base Information

Chemical Name:(2R,3S)-3-(tert-butoxycarbonyl)-5-(4-methoxybenzyl)oxy-2-vinyl-1,3-pentanediol
CAS No.:857285-42-8
Molecular Formula:C₂₀H₃₀O₆
Molecular Weight:366.455
Hs Code.:

Synonyms:(2R,3S)-3-(tert-butoxycarbonyl)-5-(4-methoxybenzyl)oxy-2-vinyl-1,3-pentanediol

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Chemical Property of (2R,3S)-3-(tert-butoxycarbonyl)-5-(4-methoxybenzyl)oxy-2-vinyl-1,3-pentanediol

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Technology Process of (2R,3S)-3-(tert-butoxycarbonyl)-5-(4-methoxybenzyl)oxy-2-vinyl-1,3-pentanediol

There total 5 articles about (2R,3S)-3-(tert-butoxycarbonyl)-5-(4-methoxybenzyl)oxy-2-vinyl-1,3-pentanediol 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: 71.0%

: 857285-41-7
(2S,3S)-3-(tert-butoxycarbonyl)-2,3-epoxy-5-(4-methoxybenzyl)oxypentan-1-ol

: 1826-67-1
vinyl magnesium bromide

: 857285-42-8
(2R,3S)-3-(tert-butoxycarbonyl)-5-(4-methoxybenzyl)oxy-2-vinyl-1,3-pentanediol

Guidance literature:: vinyl magnesium bromide; With copper(l) iodide; In tetrahydrofuran; at -26 ℃; for 0.833333h;

(2S,3S)-3-(tert-butoxycarbonyl)-2,3-epoxy-5-(4-methoxybenzyl)oxypentan-1-ol; In tetrahydrofuran; at -26 ℃; for 4h;
DOI:10.1039/b500660k

Reference yield:

: (2S,3S)-2-[2-(4-Methoxy-benzyloxy)-ethyl]-3-(tetrahydro-pyran-2-yloxymethyl)-oxirane-2-carbaldehyde

: 857285-42-8
(2R,3S)-3-(tert-butoxycarbonyl)-5-(4-methoxybenzyl)oxy-2-vinyl-1,3-pentanediol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 7.14 g / 2-methyl-2-butene; aq. Na₂HPO₄; NaClO₂ / 2-methyl-propan-2-ol / 12 h / 20 °C

2.1: 5.35 g / CH₂Cl₂ / 288 h / 20 °C

3.1: 711 mg / pyridinium p-toluenesulfonate / methanol / 39 h / 20 °C

4.1: CuI / tetrahydrofuran / 0.83 h / -26 °C

4.2: 71 percent / tetrahydrofuran / 4 h / -26 °C

With sodium chlorite; disodium hydrogenphosphate; copper(l) iodide; 2-methyl-but-2-ene; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;
DOI:10.1039/b500660k

Reference yield:

: 2,3-epoxy-2-[2-(4-methoxybenzyl)oxyethyl]-4-(tetrahydropyran-2-yl)oxybutan-1-ol

: 857285-42-8
(2R,3S)-3-(tert-butoxycarbonyl)-5-(4-methoxybenzyl)oxy-2-vinyl-1,3-pentanediol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 6.09 g / SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1 h / 20 °C

2.1: 7.14 g / 2-methyl-2-butene; aq. Na₂HPO₄; NaClO₂ / 2-methyl-propan-2-ol / 12 h / 20 °C

3.1: 5.35 g / CH₂Cl₂ / 288 h / 20 °C

4.1: 711 mg / pyridinium p-toluenesulfonate / methanol / 39 h / 20 °C

5.1: CuI / tetrahydrofuran / 0.83 h / -26 °C

5.2: 71 percent / tetrahydrofuran / 4 h / -26 °C

With sodium chlorite; disodium hydrogenphosphate; copper(l) iodide; 2-methyl-but-2-ene; pyridine-SO₃ complex; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; tert-butyl alcohol;
DOI:10.1039/b500660k