(2S)-2-{[(benzyloxy)carbonyl]amino}-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propyl acetate

Base Information

• Chemical Name: (2S)-2-{[(benzyloxy)carbonyl]amino}-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propyl acetate
• CAS No.: 213127-92-5
• Molecular Formula: C₂₄H₃₂NO₇P
• Molecular Weight: 477.494
• Mol file: 213127-92-5.mol

Synonyms:(2S)-2-{[(benzyloxy)carbonyl]amino}-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propyl acetate

Chemical Property of (2S)-2-{[(benzyloxy)carbonyl]amino}-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-{[(benzyloxy)carbonyl]amino}-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propyl acetate

There total 7 articles about (2S)-2-{[(benzyloxy)carbonyl]amino}-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propyl acetate 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: 52.0%

(2S)-3-acetoxy-2-{4-[(diethoxyphosphoryl)methyl]benzyl}propanoic acid (213127-90-3) + benzyl alcohol (100-51-6,185532-71-2) → (2S)-2-{[(benzyloxy)carbonyl]amino}-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propyl acetate (213127-92-5)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; In benzene; for 24h; Heating;

DOI:10.1016/S0040-4020(98)00586-9

Reference yield:

diethyl 4-methylbenzylphosphonate (3762-25-2) → (2S)-2-{[(benzyloxy)carbonyl]amino}-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propyl acetate (213127-92-5)

Guidance literature:

Multi-step reaction with 6 steps

1: N-bromosuccinimide; AIBN / CCl₄ / 3 h / 90 °C

2: 76 percent / NaH / tetrahydrofuran / 0.5 h / 20 °C

3: 79 percent / NaBH₄ / methanol / 2 h / 20 °C

4: 97 percent / lipase PS / tetrahydrofuran / 2 h / 25 °C / Enzymatic reaction; 2 equiv. vinyl acetate

5: Jones reagent / acetone / 4 h / 20 °C

6: 52 percent / diphenylphosphoryl azide; triethylamine / benzene / 24 h / Heating

With sodium tetrahydroborate; N-Bromosuccinimide; jones reagent; Lipase PS; 2,2'-azobis(isobutyronitrile); diphenylphosphoranyl azide; sodium hydride; triethylamine; In tetrahydrofuran; methanol; tetrachloromethane; acetone; benzene; 1: Bromination / 2: Substitution / 3: Reduction / 4: Acetylation / 5: Oxidation / 6: Rearrangement;

DOI:10.1016/S0040-4020(98)00586-9

Reference yield:

4-(diethoxyphosphorylmethyl)-1-bromomethyl-phenyl (108228-81-5) → (2S)-2-{[(benzyloxy)carbonyl]amino}-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propyl acetate (213127-92-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / NaH / tetrahydrofuran / 0.5 h / 20 °C

2: 79 percent / NaBH₄ / methanol / 2 h / 20 °C

3: 97 percent / lipase PS / tetrahydrofuran / 2 h / 25 °C / Enzymatic reaction; 2 equiv. vinyl acetate

4: Jones reagent / acetone / 4 h / 20 °C

5: 52 percent / diphenylphosphoryl azide; triethylamine / benzene / 24 h / Heating

With sodium tetrahydroborate; jones reagent; Lipase PS; diphenylphosphoranyl azide; sodium hydride; triethylamine; In tetrahydrofuran; methanol; acetone; benzene; 1: Substitution / 2: Reduction / 3: Acetylation / 4: Oxidation / 5: Rearrangement;

DOI:10.1016/S0040-4020(98)00586-9

upstream raw materials:

(2S)-3-acetoxy-2-{4-[(diethoxyphosphoryl)methyl]benzyl}propanoic acid

benzyl alcohol

diethyl 4-methylbenzylphosphonate

4-(diethoxyphosphorylmethyl)-1-bromomethyl-phenyl

Downstream raw materials:

(2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propyl acetate

diethyl [(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropyl}phenyl)methyl]phosphonate

(2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propanoic acid