(R)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-methanol

Base Information

• Chemical Name: (R)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-methanol
• CAS No.: 259867-00-0
• Molecular Formula: C₂₂H₃₂N₂O₄
• Molecular Weight: 388.507
• Mol file: 259867-00-0.mol

Synonyms:(R)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-methanol

Chemical Property of (R)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-methanol

There total 5 articles about (R)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-methanol 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: 74.0%

4-Methoxy-3-(γ,γ-dimethylallyl)benzaldehyde (56074-98-7) + (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine (109838-85-9) → (R)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-methanol (259867-00-0) + (S)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-methanol (259866-97-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 - -20 ℃;

DOI:10.1016/S0040-4039(99)01930-9

Reference yield:

4-bromo-phenol (106-41-2) → (R)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-methanol (259867-00-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Na / diethyl ether

1.2: 74 percent / ZnBr₂ / CH₂Cl₂

2.1: 93 percent / K₂CO₃ / acetone / Heating

3.1: 85 percent / t-BuLi / tetrahydrofuran / -78 °C

4.1: BuLi / tetrahydrofuran / -78 - -20 °C

With n-butyllithium; tert.-butyl lithium; sodium; potassium carbonate; In tetrahydrofuran; diethyl ether; acetone; 1.1: Metallation / 1.2: Alkylation / 2.1: Methylation / 3.1: Carbonylation / 4.1: Addition;

DOI:10.1016/S0040-4039(99)01930-9

Reference yield:

4-bromo-2-(3-methylbut-2-en-1-yl)phenol (151071-00-0) → (R)-((2S,5R)-5-Isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-methanol (259867-00-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / K₂CO₃ / acetone / Heating

2: 85 percent / t-BuLi / tetrahydrofuran / -78 °C

3: BuLi / tetrahydrofuran / -78 - -20 °C

With n-butyllithium; tert.-butyl lithium; potassium carbonate; In tetrahydrofuran; acetone; 1: Methylation / 2: Carbonylation / 3: Addition;

DOI:10.1016/S0040-4039(99)01930-9

upstream raw materials:

4-Methoxy-3-(γ,γ-dimethylallyl)benzaldehyde

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

4-bromo-phenol

4-bromo-2-(3-methylbut-2-en-1-yl)phenol

Downstream raw materials:

1-[2-(2-{2-{2-[2-(2-benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionylamino}-acetylamino)-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester

(2S,3R)-2-{2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionic acid methyl ester

cyclic Pro-Gly-Val-Gly-Tyr(β-OH,4-methyl,3-(2-methylbutyl))-Gly-Trp

(2S,3R)-2-Amino-3-hydroxy-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid methyl ester