(2S,3S)-2-(Diethoxy-phosphorylamino)-3-methyl-pentanoic acid benzyl ester

Base Information

• Chemical Name: (2S,3S)-2-(Diethoxy-phosphorylamino)-3-methyl-pentanoic acid benzyl ester
• CAS No.: 122900-74-7
• Molecular Formula: C₁₇H₂₈NO₅P
• Molecular Weight: 357.387

Synonyms:(2S,3S)-2-(Diethoxy-phosphorylamino)-3-methyl-pentanoic acid benzyl ester

Chemical Property of (2S,3S)-2-(Diethoxy-phosphorylamino)-3-methyl-pentanoic acid benzyl ester

Chemical Property:

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Technology Process of (2S,3S)-2-(Diethoxy-phosphorylamino)-3-methyl-pentanoic acid benzyl ester

There total 1 articles about (2S,3S)-2-(Diethoxy-phosphorylamino)-3-methyl-pentanoic acid benzyl 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: 81.0%

L-isoleucine benzyl ester hydrochloride (103310-88-9) + diethyl chlorophosphate (814-49-3) → (2S,3S)-2-(Diethoxy-phosphorylamino)-3-methyl-pentanoic acid benzyl ester (122900-74-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -15 - 20 ℃; for 2h;

DOI:10.1021/jm00163a044

Reference yield:

(2S,3S)-2-(Diethoxy-phosphorylamino)-3-methyl-pentanoic acid benzyl ester (122900-74-7) → N-(diethylphosphoryl)-L-isoleucyl-O-<<<<1-(benzyloxycarbonyl)-5-(carbobenzoxyamino)pentyl>amino>carbonyl>methyl>-L-tyrosylglycine methyl ester (122924-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / H₂ / 10percent Pd/C / methanol / 760 Torr

2: 1.) N,N'-carbonyldiimidazole / 1.) CH₂Cl₂, -15 deg C, 2 h, 2.) RT, overnight

With hydrogen; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In methanol;

DOI:10.1021/jm00163a044

Reference yield:

(2S,3S)-2-(Diethoxy-phosphorylamino)-3-methyl-pentanoic acid benzyl ester (122900-74-7) → N-(ethylphosphoryl)-L-isoleucyl-O-<<(N-benzylamino)carbonyl>methyl>-L-tyrosylglycine disodium salt (122923-55-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / H₂ / 10percent Pd/C / methanol / 760 Torr

2: 70 percent / DCC / dimethylformamide / 0 °C / overnight

3: 0.71 percent / aq. NaOH / ethanol / 19 h

With sodium hydroxide; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00163a044

upstream raw materials:

L-isoleucine benzyl ester hydrochloride

diethyl chlorophosphate

Downstream raw materials:

N-(diethylphosphoryl)-L-isoleucyl-O-<<<<1-(benzyloxycarbonyl)-5-(carbobenzoxyamino)pentyl>amino>carbonyl>methyl>-L-tyrosylglycine methyl ester

N-(ethylphosphoryl)-L-isoleucyl-O-<<(N-benzylamino)carbonyl>methyl>-L-tyrosylglycine disodium salt

Potassium; {(S)-3-{4-[(dibenzylcarbamoyl)-methoxy]-phenyl}-2-[(2S,3S)-2-(ethoxy-hydroxy-phosphorylamino)-3-methyl-pentanoylamino]-propionylamino}-acetate

N-(diethylphosphoryl)-L-isoleucyl-L-alanylglycyl-5-benzyl-L-glutamyl-N^G-nitro-L-arginylglycine benzyl ester

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