L-N^α-benzyloxycarbonyl-4-[(di-tert-butyl)phosphonomethyl]phenylalanine benzyl ester

Base Information

• Chemical Name: L-N^α-benzyloxycarbonyl-4-[(di-tert-butyl)phosphonomethyl]phenylalanine benzyl ester
• CAS No.: 257628-08-3
• Molecular Formula: C₃₃H₄₂NO₇P
• Molecular Weight: 595.673

Synonyms:L-N^α-benzyloxycarbonyl-4-[(di-tert-butyl)phosphonomethyl]phenylalanine benzyl ester

Chemical Property of L-N^α-benzyloxycarbonyl-4-[(di-tert-butyl)phosphonomethyl]phenylalanine benzyl ester

Chemical Property:

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Technology Process of L-N^α-benzyloxycarbonyl-4-[(di-tert-butyl)phosphonomethyl]phenylalanine benzyl ester

There total 6 articles about L-N^α-benzyloxycarbonyl-4-[(di-tert-butyl)phosphonomethyl]phenylalanine 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: 57.0%

di-tert-butyl phosphite (13086-84-5) + L-Nα-benzyloxycarbonyl-4-(bromomethyl)phenylalanine benzyl ester (257628-10-7) → L-Nα-benzyloxycarbonyl-4-[(di-tert-butyl)phosphonomethyl]phenylalanine benzyl ester (257628-08-3)

Guidance literature:

di-tert-butyl phosphite; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

L-N^α-benzyloxycarbonyl-4-(bromomethyl)phenylalanine benzyl ester; In tetrahydrofuran; at -78 - 0 ℃; for 4h;

DOI:10.1016/S0957-4166(99)00385-7

Reference yield:

L-Nα-Cbz-4-(O-trifluoromethanesulfonate)tyrosine benzyl ester (183070-41-9) → L-Nα-benzyloxycarbonyl-4-[(di-tert-butyl)phosphonomethyl]phenylalanine benzyl ester (257628-08-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 73 percent / LiCl; PdCl₂(PPh)3 / dimethylformamide / 24 h / 90 °C

2.1: 85 percent / 4-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol / 20 °C

3.1: 94 percent / aq. NaIO₄ / diethyl ether / 3 h / 20 °C

4.1: 99 percent / NaBH₄; EtOH / tetrahydrofuran / 0.33 h / 0 °C

5.1: 79 percent / CBr₄; Ph₃P / acetonitrile / 0.5 h / 20 °C

6.1: LHMDS; HMPA / tetrahydrofuran / 0.5 h / -78 °C

6.2: 57 percent / tetrahydrofuran / 4 h / -78 - 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; ethanol; carbon tetrabromide; PdCl₂(PPh)3; 4-methylmorpholine N-oxide; triphenylphosphine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Substitution / 2.1: Oxidation / 3.1: oxidative cleavage / 4.1: Reduction / 5.1: Substitution / 6.1: Metallation / 6.2: Substitution;

DOI:10.1016/S0957-4166(99)00385-7

Reference yield:

L-Nα-benzyloxycarbonyl-4-(formyl)phenylalanine benzyl ester (257628-03-8) → L-Nα-benzyloxycarbonyl-4-[(di-tert-butyl)phosphonomethyl]phenylalanine benzyl ester (257628-08-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 99 percent / NaBH₄; EtOH / tetrahydrofuran / 0.33 h / 0 °C

2.1: 79 percent / CBr₄; Ph₃P / acetonitrile / 0.5 h / 20 °C

3.1: LHMDS; HMPA / tetrahydrofuran / 0.5 h / -78 °C

3.2: 57 percent / tetrahydrofuran / 4 h / -78 - 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; ethanol; carbon tetrabromide; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; acetonitrile; 1.1: Reduction / 2.1: Substitution / 3.1: Metallation / 3.2: Substitution;

DOI:10.1016/S0957-4166(99)00385-7

upstream raw materials:

di-tert-butyl phosphite

L-N^α-benzyloxycarbonyl-4-(bromomethyl)phenylalanine benzyl ester

L-N^α-Cbz-4-(O-trifluoromethanesulfonate)tyrosine benzyl ester

L-N^α-benzyloxycarbonyl-4-(formyl)phenylalanine benzyl ester

Downstream raw materials:

L-4-((di-tert-butyl)phosphonomethyl)phenylalanine

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