(1S,2S)-N-<1-(cyclohexylmethyl)-2-(dimethoxyphosphinyl)-2-hydroxyethyl>-N²-<(1,1-dimethylethoxy)carbonyl>-L-leucinamide

Base Information

• Chemical Name: (1S,2S)-N-<1-(cyclohexylmethyl)-2-(dimethoxyphosphinyl)-2-hydroxyethyl>-N²-<(1,1-dimethylethoxy)carbonyl>-L-leucinamide
• CAS No.: 169529-79-7
• Molecular Formula: C₂₂H₄₃N₂O₇P
• Molecular Weight: 478.566

Synonyms:(1S,2S)-N-<1-(cyclohexylmethyl)-2-(dimethoxyphosphinyl)-2-hydroxyethyl>-N²-<(1,1-dimethylethoxy)carbonyl>-L-leucinamide

Chemical Property of (1S,2S)-N-<1-(cyclohexylmethyl)-2-(dimethoxyphosphinyl)-2-hydroxyethyl>-N²-<(1,1-dimethylethoxy)carbonyl>-L-leucinamide

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Technology Process of (1S,2S)-N-<1-(cyclohexylmethyl)-2-(dimethoxyphosphinyl)-2-hydroxyethyl>-N²-<(1,1-dimethylethoxy)carbonyl>-L-leucinamide

There total 2 articles about (1S,2S)-N-<1-(cyclohexylmethyl)-2-(dimethoxyphosphinyl)-2-hydroxyethyl>-N²-<(1,1-dimethylethoxy)carbonyl>-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: 53.0%

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) + -(2-amino-3-cyclohexyl-1-hydroxypropyl)phosphonic acid, dimethyl ester, hydrochloride (131372-76-4) → (1S,2S)-N-<1-(cyclohexylmethyl)-2-(dimethoxyphosphinyl)-2-hydroxyethyl>-N2-<(1,1-dimethylethoxy)carbonyl>-L-leucinamide (169529-79-7)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In N,N-dimethyl-formamide; at 25 ℃; for 16h;

DOI:10.1021/jm00022a022

Reference yield:

<1-(cyclohexylmethyl)-2-(dimethoxyphosphinyl)-2-hydroxyethyl>carbamic acid, 1,1-dimethylethyl ester → (1S,2S)-N-<1-(cyclohexylmethyl)-2-(dimethoxyphosphinyl)-2-hydroxyethyl>-N2-<(1,1-dimethylethoxy)carbonyl>-L-leucinamide (169529-79-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86.6 percent / HCl / ethyl acetate / 6.5 h / 0 °C

2: 53 percent / HOBt, Et₃N, EDC / dimethylformamide / 16 h / 25 °C

With hydrogenchloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00022a022

Reference yield: 100.0%

(1S,2S)-N-<1-(cyclohexylmethyl)-2-(dimethoxyphosphinyl)-2-hydroxyethyl>-N2-<(1,1-dimethylethoxy)carbonyl>-L-leucinamide (169529-79-7) → (1S,2S)-N-<1-(cyclohexylmethyl)-2-(dimethoxyphosphinyl)-2-hydroxyethyl>-L-leucinamide, hydrochloride

Guidance literature:

With hydrogenchloride; In ethyl acetate; for 1h;

DOI:10.1021/jm00022a022

upstream raw materials:

N-tert-butoxycarbonyl-L-leucine

-(2-amino-3-cyclohexyl-1-hydroxypropyl)phosphonic acid, dimethyl ester, hydrochloride

Downstream raw materials:

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

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