(R)-2-Acetylamino-3-{(1R,2S)-2-[2-(diethoxy-phosphoryl)-ethyl]-cyclohexyl}-propionic acid methyl ester

Base Information

• Chemical Name: (R)-2-Acetylamino-3-{(1R,2S)-2-[2-(diethoxy-phosphoryl)-ethyl]-cyclohexyl}-propionic acid methyl ester
• CAS No.: 144236-12-4
• Molecular Formula: C₁₈H₃₄NO₆P
• Molecular Weight: 391.445
• Mol file: 144236-12-4.mol

Synonyms:(R)-2-Acetylamino-3-{(1R,2S)-2-[2-(diethoxy-phosphoryl)-ethyl]-cyclohexyl}-propionic acid methyl ester

Chemical Property of (R)-2-Acetylamino-3-{(1R,2S)-2-[2-(diethoxy-phosphoryl)-ethyl]-cyclohexyl}-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-Acetylamino-3-{(1R,2S)-2-[2-(diethoxy-phosphoryl)-ethyl]-cyclohexyl}-propionic acid methyl ester

There total 12 articles about (R)-2-Acetylamino-3-{(1R,2S)-2-[2-(diethoxy-phosphoryl)-ethyl]-cyclohexyl}-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:

(E)-2-Acetylamino-3-{(1S,2S)-2-[2-(diethoxy-phosphoryl)-ethyl]-cyclohexyl}-acrylic acid methyl ester (144236-11-3) → (S)-2-Acetylamino-3-{(1R,2S)-2-[2-(diethoxy-phosphoryl)-ethyl]-cyclohexyl}-propionic acid (144236-13-5) + (R)-2-Acetylamino-3-{(1R,2S)-2-[2-(diethoxy-phosphoryl)-ethyl]-cyclohexyl}-propionic acid methyl ester (144236-12-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 4h; under 2585.7 Torr;

DOI:10.1021/jo00077a058

Reference yield:

(1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid (31139-02-3,31139-03-4,56124-48-2,88335-93-7,88335-94-8,93603-11-3) → (R)-2-Acetylamino-3-{(1R,2S)-2-[2-(diethoxy-phosphoryl)-ethyl]-cyclohexyl}-propionic acid methyl ester (144236-12-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 78 percent / LiEt₃BH / tetrahydrofuran / Ambient temperature

2: DIBAL / toluene / 1 h / -45 - -35 °C

3: NaH / tetrahydrofuran; toluene / 1.) r.t., 1 h, 2.) 0 deg C, 30 min; 60 deg C, 4 h

4: H₂ / Pd/C

5: 84 percent / oxalyl chloride, DMSO, triethylamine / CH₂Cl₂ / - 60 deg C, 30 min; r.t., 30 min

6: NaH / tetrahydrofuran / 24 h / Ambient temperature

7: H₂ / 5percent Pd/C / ethanol / 4 h / 2585.7 Torr

With oxalyl dichloride; hydrogen; sodium hydride; diisobutylaluminium hydride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/jo00077a058

Reference yield:

(3aS,7aR)-3a,4,7,7a-tetrahydroisobenzofuran-1(3H)-one (88586-06-5) → (R)-2-Acetylamino-3-{(1R,2S)-2-[2-(diethoxy-phosphoryl)-ethyl]-cyclohexyl}-propionic acid methyl ester (144236-12-4)

Guidance literature:

Multi-step reaction with 6 steps

1: DIBAL / toluene / 1 h / -45 - -35 °C

2: NaH / tetrahydrofuran; toluene / 1.) r.t., 1 h, 2.) 0 deg C, 30 min; 60 deg C, 4 h

3: H₂ / Pd/C

4: 84 percent / oxalyl chloride, DMSO, triethylamine / CH₂Cl₂ / - 60 deg C, 30 min; r.t., 30 min

5: NaH / tetrahydrofuran / 24 h / Ambient temperature

6: H₂ / 5percent Pd/C / ethanol / 4 h / 2585.7 Torr

With oxalyl dichloride; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/jo00077a058

upstream raw materials:

(E)-2-Acetylamino-3-{(1S,2S)-2-[2-(diethoxy-phosphoryl)-ethyl]-cyclohexyl}-acrylic acid methyl ester

(3aS,7aR)-3a,4,7,7a-tetrahydroisobenzofuran-1(3H)-one

(1S,6R)-8-oxabicyclo[4.3.0]nonan-7-one

(1S,6R,7RS)-7-hydroxy-8-oxabicyclo[4.3.0]nonane

Downstream raw materials:

NPC 17742