(2R,3S)-dimethyl <3-<<<(tert-butyloxycarbonyl)phenylalaninyl>leucyl>amino>-4-cyclohexyl-2-hydroxybutyl>phosphonate

Base Information

• Chemical Name: (2R,3S)-dimethyl <3-<<<(tert-butyloxycarbonyl)phenylalaninyl>leucyl>amino>-4-cyclohexyl-2-hydroxybutyl>phosphonate
• CAS No.: 123381-46-4
• Molecular Formula: C₃₂H₅₄N₃O₈P
• Molecular Weight: 639.77
• Mol file: 123381-46-4.mol

Synonyms:(2R,3S)-dimethyl <3-<<<(tert-butyloxycarbonyl)phenylalaninyl>leucyl>amino>-4-cyclohexyl-2-hydroxybutyl>phosphonate

Chemical Property of (2R,3S)-dimethyl <3-<<<(tert-butyloxycarbonyl)phenylalaninyl>leucyl>amino>-4-cyclohexyl-2-hydroxybutyl>phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-dimethyl <3-<<<(tert-butyloxycarbonyl)phenylalaninyl>leucyl>amino>-4-cyclohexyl-2-hydroxybutyl>phosphonate

There total 4 articles about (2R,3S)-dimethyl <3-<<<(tert-butyloxycarbonyl)phenylalaninyl>leucyl>amino>-4-cyclohexyl-2-hydroxybutyl>phosphonate 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: 77.0%

tert-butoxycarbonyl-L-phenylalanyl-L-leucine (33014-68-5) + ((S)-3-Amino-4-cyclohexyl-2-hydroxy-butyl)-phosphonic acid dimethyl ester; hydrochloride (123381-48-6,123381-49-7) → (2R,3S)-dimethyl <3-<<<(tert-butyloxycarbonyl)phenylalaninyl>leucyl>amino>-4-cyclohexyl-2-hydroxybutyl>phosphonate (123381-46-4)

Guidance literature:

With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; 1.) -23 deg C, 2 h, 2.) room temp.;

DOI:10.1021/jm00164a011

Reference yield:

N-tritylcyclohexylalaninol (123381-14-6) → (2R,3S)-dimethyl <3-<<<(tert-butyloxycarbonyl)phenylalaninyl>leucyl>amino>-4-cyclohexyl-2-hydroxybutyl>phosphonate (123381-46-4)

Guidance literature:

Multi-step reaction with 4 steps

1: oxalyl chloride, dimethylsulfoxide, triethylamine / CH₂Cl₂ / 0.5 h / -60 °C

2: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) 0.5 h

3: 4.5 M HCl / dioxane / 0.5 h / Ambient temperature

4: 77 percent / 1-hydroxybenzotriazole monohydrate, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 1.) -23 deg C, 2 h, 2.) room temp.

With 4-methyl-morpholine; hydrogenchloride; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00164a011

Reference yield:

N-tritylcyclohexylalaninal (112190-46-2) → (2R,3S)-dimethyl <3-<<<(tert-butyloxycarbonyl)phenylalaninyl>leucyl>amino>-4-cyclohexyl-2-hydroxybutyl>phosphonate (123381-46-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) 0.5 h

2: 4.5 M HCl / dioxane / 0.5 h / Ambient temperature

3: 77 percent / 1-hydroxybenzotriazole monohydrate, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 1.) -23 deg C, 2 h, 2.) room temp.

With 4-methyl-morpholine; hydrogenchloride; n-butyllithium; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jm00164a011

upstream raw materials:

tert-butoxycarbonyl-L-phenylalanyl-L-leucine

((S)-3-Amino-4-cyclohexyl-2-hydroxy-butyl)-phosphonic acid dimethyl ester; hydrochloride

N-tritylcyclohexylalaninol

N-tritylcyclohexylalaninal

Downstream raw materials:

(2R,3S)-methyl <3-<<<(tert-butyloxycarbonyl)phenylalaninyl>leucyl>amino>-4-cyclohexyl-2-hydroxybutyl>phosphonate