(2R,5S,1'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine

Base Information

• Chemical Name: (2R,5S,1'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine
• CAS No.: 182207-35-8
• Molecular Formula: C₂₅H₄₁N₂O₆P
• Molecular Weight: 496.584
• Mol file: 182207-35-8.mol

Synonyms:(2R,5S,1'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine

Chemical Property of (2R,5S,1'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S,1'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine

There total 4 articles about (2R,5S,1'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-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: 15.0%

(3S)-3,6-dihydro-2,5-diethoxy-3-isopropylpyrazine (134870-62-5) + (1Z)-[3-(benzyloxy)-1-propenyl]phosphonic acid diethyl ester (618892-44-7) → (2R,5S,1'S)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine (618892-48-1) + (2R,5S,1'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine (182207-35-8) + [5-Benzyloxy-2-benzyloxymethyl-4-((S)-3,6-diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl)-3-(diethoxy-phosphoryl)-pentyl]-phosphonic acid diethyl ester

Guidance literature:

(3S)-3,6-dihydro-2,5-diethoxy-3-isopropylpyrazine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(1Z)-[3-(benzyloxy)-1-propenyl]phosphonic acid diethyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

DOI:10.1021/jo034707q

Reference yield:

2-Benzyloxyethanol (622-08-2,1201808-31-2) → (2R,5S,1'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine (182207-35-8)

Guidance literature:

Multi-step reaction with 3 steps

1: PCC

2: 1.) LDA, ClPO₃Et₂ / 1.) THF, -78 deg C; 2.) THF, -78 deg C to 0 deg C

3: tetrahydrofuran / 0.08 h / -78 °C

With diethyl chlorophosphate; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)01230-0

Reference yield:

benzyloxyacetoaldehyde (60656-87-3) → (2R,5S,1'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine (182207-35-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA, ClPO₃Et₂ / 1.) THF, -78 deg C; 2.) THF, -78 deg C to 0 deg C

2: tetrahydrofuran / 0.08 h / -78 °C

With diethyl chlorophosphate; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)01230-0

upstream raw materials:

(3S)-3,6-dihydro-2,5-diethoxy-3-isopropylpyrazine

(1E)-(3-benzyloxypropen-1-yl)phosphonic acid diethyl ester

(1Z)-[3-(benzyloxy)-1-propenyl]phosphonic acid diethyl ester

2-Benzyloxyethanol

Downstream raw materials:

ethyl (2R,3R)-2-amino-3-(benzyloxymethyl)-4-(diethoxyphosphoryl)butanoate