(S,E)-1-[α-deuterio(2-methoxybenzyl)oxy]-2-(triisopropylsilyloxymethyl)but-2-ene

Base Information

• Chemical Name: (S,E)-1-[α-deuterio(2-methoxybenzyl)oxy]-2-(triisopropylsilyloxymethyl)but-2-ene
• CAS No.: 1374335-99-5
• Molecular Formula: C₂₂H₃₈O₃Si
• Molecular Weight: 379.619
• Mol file: 1374335-99-5.mol

Synonyms:(S,E)-1-[α-deuterio(2-methoxybenzyl)oxy]-2-(triisopropylsilyloxymethyl)but-2-ene

Chemical Property of (S,E)-1-[α-deuterio(2-methoxybenzyl)oxy]-2-(triisopropylsilyloxymethyl)but-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-1-[α-deuterio(2-methoxybenzyl)oxy]-2-(triisopropylsilyloxymethyl)but-2-ene

There total 2 articles about (S,E)-1-[α-deuterio(2-methoxybenzyl)oxy]-2-(triisopropylsilyloxymethyl)but-2-ene 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: 67.0%

(Z)-1-bromo-2-(triisopropylsilyloxymethyl)but-2-ene (1044749-61-2) + (S)-α-deuterio-2-methoxybenzyl alcohol (1374335-95-1) → (S,E)-1-[α-deuterio(2-methoxybenzyl)oxy]-2-(triisopropylsilyloxymethyl)but-2-ene (1374335-99-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tet.2012.03.059

Reference yield:

2-methoxybenzaldehyde-α-d1 (13278-00-7) → (S,E)-1-[α-deuterio(2-methoxybenzyl)oxy]-2-(triisopropylsilyloxymethyl)but-2-ene (1374335-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; bis(acetato){(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl}rutenium(II); hydrogen / tetrahydrofuran; methanol; water / 24 h / 20 °C / 3000.3 Torr

2: potassium tert-butylate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

With hydrogenchloride; bis(acetato){(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl}rutenium(II); potassium tert-butylate; hydrogen; In tetrahydrofuran; methanol; water;

DOI:10.1016/j.tet.2012.03.059

Reference yield:

(S,E)-1-[α-deuterio(2-methoxybenzyl)oxy]-2-(triisopropylsilyloxymethyl)but-2-ene (1374335-99-5) → (1R,2S)-1-deuterio-1-(2-methoxyphenyl)-2-methyl-3-(triisopropylsilyloxymethyl)-but-3-en-1-ol (1374336-02-3) + (1S,2R)-1-deuterio-1-(2-methoxyphenyl)-2-methyl-3-(triisopropylsilyloxymethyl)-but-3-en-1-ol (1374336-01-2)

Guidance literature:

(S,E)-1-[α-deuterio(2-methoxybenzyl)oxy]-2-(triisopropylsilyloxymethyl)but-2-ene; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 2h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; pentane; at -78 - 20 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2012.03.059

upstream raw materials:

(Z)-1-bromo-2-(triisopropylsilyloxymethyl)but-2-ene

(S)-α-deuterio-2-methoxybenzyl alcohol

2-methoxybenzaldehyde-α-d₁

Downstream raw materials:

(1R,2S)-1-deuterio-1-(2-methoxyphenyl)-2-methyl-3-(triisopropylsilyloxymethyl)-but-3-en-1-ol

(1S,2R)-1-deuterio-1-(2-methoxyphenyl)-2-methyl-3-(triisopropylsilyloxymethyl)-but-3-en-1-ol