(1S,2S)-N-<1-(cyclohexylmethyl)-2-(diethoxyphosphinyl)-2-hydroxyethyl>-N²--L-phenylalanyl>-L-leucinamide

Base Information

• Chemical Name: (1S,2S)-N-<1-(cyclohexylmethyl)-2-(diethoxyphosphinyl)-2-hydroxyethyl>-N²--L-phenylalanyl>-L-leucinamide
• CAS No.: 169529-76-4
• Molecular Formula: C₃₃H₅₆N₃O₈P
• Molecular Weight: 653.797

Synonyms:(1S,2S)-N-<1-(cyclohexylmethyl)-2-(diethoxyphosphinyl)-2-hydroxyethyl>-N²--L-phenylalanyl>-L-leucinamide

Chemical Property of (1S,2S)-N-<1-(cyclohexylmethyl)-2-(diethoxyphosphinyl)-2-hydroxyethyl>-N²--L-phenylalanyl>-L-leucinamide

Chemical Property:

Purity/Quality:

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Technology Process of (1S,2S)-N-<1-(cyclohexylmethyl)-2-(diethoxyphosphinyl)-2-hydroxyethyl>-N²--L-phenylalanyl>-L-leucinamide

There total 3 articles about (1S,2S)-N-<1-(cyclohexylmethyl)-2-(diethoxyphosphinyl)-2-hydroxyethyl>-N²--L-phenylalanyl>-L-leucinamide 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:

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal (98105-42-1) → (1S,2S)-N-<1-(cyclohexylmethyl)-2-(diethoxyphosphinyl)-2-hydroxyethyl>-N2--L-phenylalanyl>-L-leucinamide (169529-76-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 77.4 percent / KF / CH₂Cl₂ / 18 h / Ambient temperature

2: 88.8 percent / HCl / ethyl acetate / 0.25 h / 0 °C

3: 1.) HOBt, 2.) iPr₂NEt, DCC / 1.) DMF, 0 deg C, 5 min, 2.)a) DMF, 0 deg C, 2 h, b) RT, overnight

With hydrogenchloride; potassium fluoride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane; ethyl acetate;

DOI:10.1021/jm00022a022

Reference yield:

(1S)-<1-(cyclohexylmethyl)-2-(diethoxyphosphinyl)-2-hydroxyethyl>carbamic acid, 1,1-dimethylethyl ester → (1S,2S)-N-<1-(cyclohexylmethyl)-2-(diethoxyphosphinyl)-2-hydroxyethyl>-N2--L-phenylalanyl>-L-leucinamide (169529-76-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 88.8 percent / HCl / ethyl acetate / 0.25 h / 0 °C

2: 1.) HOBt, 2.) iPr₂NEt, DCC / 1.) DMF, 0 deg C, 5 min, 2.)a) DMF, 0 deg C, 2 h, b) RT, overnight

With hydrogenchloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In ethyl acetate;

DOI:10.1021/jm00022a022

Reference yield:

tert-butoxycarbonyl-L-phenylalanyl-L-leucine (33014-68-5) + ((S)-2-Amino-3-cyclohexyl-1-hydroxy-propyl)-phosphonic acid diethyl ester; hydrochloride → (1S,2S)-N-<1-(cyclohexylmethyl)-2-(diethoxyphosphinyl)-2-hydroxyethyl>-N2--L-phenylalanyl>-L-leucinamide (169529-76-4) + (1S,2R)-N-<1-(cyclohexylmethyl)-2-(diethoxyphosphinyl)-2-hydroxyethyl>-N2--L-phenylalanyl>-L-leucinamide

Guidance literature:

With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; Yield given. Multistep reaction; 1.) DMF, 0 deg C, 5 min, 2.)a) DMF, 0 deg C, 2 h, b) RT, overnight;

DOI:10.1021/jm00022a022

upstream raw materials:

tert-butoxycarbonyl-L-phenylalanyl-L-leucine

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal

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