(2R,5S,αS)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine

Base Information

• Chemical Name: (2R,5S,αS)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine
• CAS No.: 188446-23-3
• Molecular Formula: C₂₃H₂₈N₂O₄
• Molecular Weight: 396.486
• Mol file: 188446-23-3.mol

Synonyms:(2R,5S,αS)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine

Chemical Property of (2R,5S,αS)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S,αS)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine

There total 1 articles about (2R,5S,αS)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine 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: 45.0%

p-benzyloxybenzaldehyde (4397-53-9) + (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine (109838-85-9) → (2R,5S,αR)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (188446-24-4) + (2R,5S,αS)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (188446-23-3)

Guidance literature:

(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere;

p-benzyloxybenzaldehyde; In tetrahydrofuran; for 1.5h; Inert atmosphere;

DOI:10.1002/chem.201701259

Reference yield: 72.0%

(2R,5S,αS)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (188446-23-3) + methyl iodide (74-88-4) → (2R,5S,αS)-5-[4'-benzyloxy-α-methoxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (864954-42-7)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1021/jo0508853

Reference yield: 48.0%

(2R,5S,αS)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (188446-23-3) → methyl (2S,3S)-2-amino-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate (188446-25-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; acetonitrile; at 20 ℃; for 22h; Inert atmosphere;

DOI:10.1002/chem.201701259

upstream raw materials:

p-benzyloxybenzaldehyde

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

Downstream raw materials:

methyl (2S,3S)-2-amino-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate

(2R,5S,αS)-5-[4'-benzyloxy-α-methoxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine

(2S,3S)-2-amino-3-(4-hydroxyphenyl)-3-methoxypropanoic acid

(S)-O-benzyl-β-methoxy-L-tyrosine methyl ester