Pyrazine, 3,6-diethoxy-2,5-dihydro-2-[(2S)-3-methyl-2-[(phenylmethoxy)methyl]but yl]-, (2R)-

Base Information

• Chemical Name: Pyrazine, 3,6-diethoxy-2,5-dihydro-2-[(2S)-3-methyl-2-[(phenylmethoxy)methyl]but yl]-, (2R)-
• CAS No.: 173007-37-9
• Molecular Formula: C₂₁H₃₂N₂O₃
• Molecular Weight: 360.497
• Mol file: 173007-37-9.mol

Synonyms:

Chemical Property of Pyrazine, 3,6-diethoxy-2,5-dihydro-2-[(2S)-3-methyl-2-[(phenylmethoxy)methyl]but yl]-, (2R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pyrazine, 3,6-diethoxy-2,5-dihydro-2-[(2S)-3-methyl-2-[(phenylmethoxy)methyl]but yl]-, (2R)-

There total 6 articles about Pyrazine, 3,6-diethoxy-2,5-dihydro-2-[(2S)-3-methyl-2-[(phenylmethoxy)methyl]but yl]-, (2R)- 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:

(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine (109838-85-9) + (2S)-(benzyloxymethyl)-3-methyl-butyl bromide (172901-00-7) → (2R)-2-{(2S)-2-[(benzyloxy)methyl]-3-methylbutyl}-3,6-diethoxy-2,5-dihydropyrazine (173007-37-9) + (2S)-2-{(2S)-2-[(benzyloxy)methyl]-3-methylbutyl}-3,6-diethoxy-2,5-dihydropyrazine (172900-78-6)

Guidance literature:

(2S)-(benzyloxymethyl)-3-methyl-butyl bromide; With n-butyllithium; In tetrahydrofuran; at -40 ℃;

(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine; In tetrahydrofuran; at -40 - -18 ℃; for 16h; Title compound not separated from byproducts;

DOI:10.1002/hlca.200390235

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (2R)-2-{(2S)-2-[(benzyloxy)methyl]-3-methylbutyl}-3,6-diethoxy-2,5-dihydropyrazine (173007-37-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: TiCl₄; Huenig'base / CH₂Cl₂ / 1 h / 0 °C

1.2: 50 percent / CH₂Cl₂ / 20 h / 0 °C

2.1: H₂O₂; LiOH / tetrahydrofuran; H₂O / 0 - 2 °C

2.2: 92 percent / tetrahydrofuran; H₂O / 16 h / 20 °C

3.1: NaBH₄ / tetrahydrofuran / 0.67 h / 10 - 20 °C

3.2: I₂ / tetrahydrofuran / 72 h / 20 °C

3.3: 92 percent / tetrahydrofuran; methanol / 1 h / 20 °C

4.1: 70 percent / Ph₃P; NBS / 20 °C

5.1: BuLi / tetrahydrofuran / -40 °C

5.2: tetrahydrofuran / 16 h / -40 - -18 °C

With lithium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; dihydrogen peroxide; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/hlca.200390235

Reference yield:

(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one (145589-03-3) → (2R)-2-{(2S)-2-[(benzyloxy)methyl]-3-methylbutyl}-3,6-diethoxy-2,5-dihydropyrazine (173007-37-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: TiCl₄; Huenig'base / CH₂Cl₂ / 1 h / 0 °C

1.2: 50 percent / CH₂Cl₂ / 20 h / 0 °C

2.1: H₂O₂; LiOH / tetrahydrofuran; H₂O / 0 - 2 °C

2.2: 92 percent / tetrahydrofuran; H₂O / 16 h / 20 °C

3.1: NaBH₄ / tetrahydrofuran / 0.67 h / 10 - 20 °C

3.2: I₂ / tetrahydrofuran / 72 h / 20 °C

3.3: 92 percent / tetrahydrofuran; methanol / 1 h / 20 °C

4.1: 70 percent / Ph₃P; NBS / 20 °C

5.1: BuLi / tetrahydrofuran / -40 °C

5.2: tetrahydrofuran / 16 h / -40 - -18 °C

With lithium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; dihydrogen peroxide; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/hlca.200390235

upstream raw materials:

(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine

(2S)-(benzyloxymethyl)-3-methyl-butyl bromide

Benzyloxymethyl chloride

(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one

Refernces