(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
• Mol file: 857285-42-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

(2S,3S)-3-(tert-butoxycarbonyl)-2,3-epoxy-5-(4-methoxybenzyl)oxypentan-1-ol (857285-41-7) + vinyl magnesium bromide (1826-67-1) → (2R,3S)-3-(tert-butoxycarbonyl)-5-(4-methoxybenzyl)oxy-2-vinyl-1,3-pentanediol (857285-42-8)

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

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

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

upstream raw materials:

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

vinyl magnesium bromide