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

Base Information

• Chemical Name: (2S,3R)-2-Amino-3-hydroxy-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid methyl ester
• CAS No.: 259867-05-5
• Molecular Formula: C₁₆H₂₃NO₄
• Molecular Weight: 293.363
• Mol file: 259867-05-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (2S,3R)-2-Amino-3-hydroxy-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid methyl ester 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: 56.0%

(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) → (2S,3R)-2-Amino-3-hydroxy-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid methyl ester (259867-05-5)

Guidance literature:

With trifluoroacetic acid; In water;

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

Reference yield:

4-bromo-phenol (106-41-2) → (2S,3R)-2-Amino-3-hydroxy-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid methyl ester (259867-05-5)

Guidance literature:

Multi-step reaction with 5 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

5.1: 56 percent / TFA / H₂O

With n-butyllithium; tert.-butyl lithium; sodium; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; water; acetone; 1.1: Metallation / 1.2: Alkylation / 2.1: Methylation / 3.1: Carbonylation / 4.1: Addition / 5.1: Hydrolysis;

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

Reference yield:

4-Methoxy-3-(γ,γ-dimethylallyl)benzaldehyde (56074-98-7) → (2S,3R)-2-Amino-3-hydroxy-3-[4-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-propionic acid methyl ester (259867-05-5)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 56 percent / TFA / H₂O

With n-butyllithium; trifluoroacetic acid; In tetrahydrofuran; water; 1: Addition / 2: Hydrolysis;

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

upstream raw materials:

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

4-bromo-phenol

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

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