[benzyloxycarbonylamino-(2-hydroxy-propylcarbamoyl)-methyl]-phosphonic acid dimethyl ester

Base Information

• Chemical Name: [benzyloxycarbonylamino-(2-hydroxy-propylcarbamoyl)-methyl]-phosphonic acid dimethyl ester
• CAS No.: 352273-45-1
• Molecular Formula: C₁₅H₂₃N₂O₇P
• Molecular Weight: 374.331
• Mol file: 352273-45-1.mol

Synonyms:[benzyloxycarbonylamino-(2-hydroxy-propylcarbamoyl)-methyl]-phosphonic acid dimethyl ester

Chemical Property of [benzyloxycarbonylamino-(2-hydroxy-propylcarbamoyl)-methyl]-phosphonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [benzyloxycarbonylamino-(2-hydroxy-propylcarbamoyl)-methyl]-phosphonic acid dimethyl ester

There total 2 articles about [benzyloxycarbonylamino-(2-hydroxy-propylcarbamoyl)-methyl]-phosphonic acid dimethyl 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: 86.0%

(+/-)-2-<(benzyloxycarbonyl)amino>-2-(dimethoxyphosphinyl)acetic acid (89525-07-5) + 3-amino-2-propanol (78-96-6,1674-56-2) → [benzyloxycarbonylamino-(2-hydroxy-propylcarbamoyl)-methyl]-phosphonic acid dimethyl ester (352273-45-1)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 25 ℃; for 24h;

DOI:10.1016/S1874-6004(04)80025-X

Reference yield:

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) → [benzyloxycarbonylamino-(2-hydroxy-propylcarbamoyl)-methyl]-phosphonic acid dimethyl ester (352273-45-1)

Guidance literature:

Multi-step reaction with 2 steps

1: LiOH / tetrahydrofuran; methanol; H₂O / 0.5 h / 25 °C

2: 86 percent / DCC; HOBt / CH₂Cl₂ / 24 h / 0 - 25 °C

With lithium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/S1874-6004(04)80025-X

Reference yield:

[benzyloxycarbonylamino-(2-hydroxy-propylcarbamoyl)-methyl]-phosphonic acid dimethyl ester (352273-45-1) → (S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-[(S)-2-(3-methoxy-5-methyl-naphthalene-1-carbonyloxy)-2-((S)-2-methyl-oxiranyl)-acetylamino]-4-(2-oxo-propylcarbamoyl)-1-triethylsilanyloxy-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester (352273-49-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / H₂ / Pd/C / methanol / 2 h / 25 °C / 760 Torr

2: 79 percent / EDCI; HOBt / CH₂Cl₂ / 9 h / 0 - 25 °C

3: 83 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

4: tBuOK / tetrahydrofuran / 18 h / -50 °C

With oxalyl dichloride; potassium tert-butylate; hydrogen; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 3: Swern oxidation / 4: Wadsworth-Horner-Emmons olefination;

DOI:10.1016/S1874-6004(04)80025-X

upstream raw materials:

(+/-)-2-<(benzyloxycarbonyl)amino>-2-(dimethoxyphosphinyl)acetic acid

3-amino-2-propanol

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

Downstream raw materials:

(S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-[(S)-2-(3-methoxy-5-methyl-naphthalene-1-carbonyloxy)-2-((S)-2-methyl-oxiranyl)-acetylamino]-4-(2-oxo-propylcarbamoyl)-1-triethylsilanyloxy-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

(S)-2-[(1R,2S)-2-Acetoxy-3-bromo-4-[(Z)-(S)-2-(3-methoxy-5-methyl-naphthalene-1-carbonyloxy)-2-((S)-2-methyl-oxiranyl)-acetylimino]-4-(2-oxo-propylcarbamoyl)-1-triethylsilanyloxy-butyl]-aziridine-1-carboxylic acid benzyl ester