(2R,5S)-2-Isopropyl-3,6-dimethoxy-5-(2-phenylsulfanyl-allyl)-2,5-dihydro-pyrazine

Base Information

• Chemical Name: (2R,5S)-2-Isopropyl-3,6-dimethoxy-5-(2-phenylsulfanyl-allyl)-2,5-dihydro-pyrazine
• CAS No.: 203920-11-0
• Molecular Formula: C₁₈H₂₄N₂O₂S
• Molecular Weight: 332.467
• Mol file: 203920-11-0.mol

Synonyms:(2R,5S)-2-Isopropyl-3,6-dimethoxy-5-(2-phenylsulfanyl-allyl)-2,5-dihydro-pyrazine

Chemical Property of (2R,5S)-2-Isopropyl-3,6-dimethoxy-5-(2-phenylsulfanyl-allyl)-2,5-dihydro-pyrazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S)-2-Isopropyl-3,6-dimethoxy-5-(2-phenylsulfanyl-allyl)-2,5-dihydro-pyrazine

There total 2 articles about (2R,5S)-2-Isopropyl-3,6-dimethoxy-5-(2-phenylsulfanyl-allyl)-2,5-dihydro-pyrazine 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:

benzenesulfenyl chloride (931-59-9) → (2R,5S)-2-Isopropyl-3,6-dimethoxy-5-(2-phenylsulfanyl-allyl)-2,5-dihydro-pyrazine (203920-11-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 0.5 h / -30 - -20 °C

2: 1) n-BuLi / 1) THF, hexane, -78 deg C, 10 min, 2) THF, hexane, -60 deg C, 4 h; -60 deg C to room temperature, 12 h

With n-butyllithium; In tetrahydrofuran;

DOI:10.1021/jo972133h

Reference yield:

1-Chlor-2-phenylthio-2-propen (15893-06-8) + (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine (109838-85-9) → (2R,5S)-2-Isopropyl-3,6-dimethoxy-5-(2-phenylsulfanyl-allyl)-2,5-dihydro-pyrazine (203920-11-0)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1) THF, hexane, -78 deg C, 10 min, 2) THF, hexane, -60 deg C, 4 h; -60 deg C to room temperature, 12 h;

DOI:10.1021/jo972133h

Reference yield: 79.0%

(2R,5S)-2-Isopropyl-3,6-dimethoxy-5-(2-phenylsulfanyl-allyl)-2,5-dihydro-pyrazine (203920-11-0) → D-Valine methyl ester (4070-48-8,18869-42-6,21685-47-2) + (S)-2-Amino-4-phenylsulfanyl-pent-4-enoic acid methyl ester (203920-12-1)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1021/jo972133h

upstream raw materials:

1-Chlor-2-phenylthio-2-propen

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

benzenesulfenyl chloride

Downstream raw materials:

D-Valine methyl ester

(S)-2-Amino-4-phenylsulfanyl-pent-4-enoic acid methyl ester

(2R,6S)-2,6-diaminoheptanedioic acid

(S,S)-2,6-diaminopimelic acid