(1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl[(2S)-2-({[(1S)-2-methoxy-1-methyl-2-oxoethyl]amino}carbonyl)pent-4-ynyl]phosphinic acid

Base Information

• Chemical Name: (1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl[(2S)-2-({[(1S)-2-methoxy-1-methyl-2-oxoethyl]amino}carbonyl)pent-4-ynyl]phosphinic acid
• CAS No.: 583866-47-1
• Molecular Formula: C₂₆H₃₁N₂O₇P
• Molecular Weight: 514.515
• Mol file: 583866-47-1.mol

Synonyms:(1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl[(2S)-2-({[(1S)-2-methoxy-1-methyl-2-oxoethyl]amino}carbonyl)pent-4-ynyl]phosphinic acid

Chemical Property of (1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl[(2S)-2-({[(1S)-2-methoxy-1-methyl-2-oxoethyl]amino}carbonyl)pent-4-ynyl]phosphinic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl[(2S)-2-({[(1S)-2-methoxy-1-methyl-2-oxoethyl]amino}carbonyl)pent-4-ynyl]phosphinic acid

There total 4 articles about (1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl[(2S)-2-({[(1S)-2-methoxy-1-methyl-2-oxoethyl]amino}carbonyl)pent-4-ynyl]phosphinic acid 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: 79.0%

L-alanine methyl ester hydrochloride (2491-20-5) + (2S)-2-{[((1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl)(hydroxy)phosphoryl]methyl}pent-4-ynoic acid (583866-40-4) → (1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl[(2S)-2-({[(1S)-2-methoxy-1-methyl-2-oxoethyl]amino}carbonyl)pent-4-ynyl]phosphinic acid (583866-47-1)

Guidance literature:

With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1002/chem.200204456

Reference yield:

ethyl α-propargyl acrylate (54109-54-5) → (1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl[(2S)-2-({[(1S)-2-methoxy-1-methyl-2-oxoethyl]amino}carbonyl)pent-4-ynyl]phosphinic acid (583866-47-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HMDS / 1 h / 110 °C

1.2: 96 percent / 3 h / 100 - 105 °C

2.1: aq. NaOH / ethanol / 20 °C

3.1: 79 percent / DIPEA; HOBt / CH₂Cl₂ / 1.5 h / 20 °C

With sodium hydroxide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In ethanol; dichloromethane; 1.2: Michael addition;

DOI:10.1002/chem.200204456

Reference yield:

((R)-1-(((benzyloxy)carbonyl)amino)-2-phenylethyl)phosphinic acid (118636-74-1) → (1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl[(2S)-2-({[(1S)-2-methoxy-1-methyl-2-oxoethyl]amino}carbonyl)pent-4-ynyl]phosphinic acid (583866-47-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HMDS / 1 h / 110 °C

1.2: 96 percent / 3 h / 100 - 105 °C

2.1: aq. NaOH / ethanol / 20 °C

3.1: 79 percent / DIPEA; HOBt / CH₂Cl₂ / 1.5 h / 20 °C

With sodium hydroxide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In ethanol; dichloromethane; 1.2: Michael addition;

DOI:10.1002/chem.200204456

upstream raw materials:

L-alanine methyl ester hydrochloride

(2S)-2-{[((1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl)(hydroxy)phosphoryl]methyl}pent-4-ynoic acid

ethyl α-propargyl acrylate

((R)-1-(((benzyloxy)carbonyl)amino)-2-phenylethyl)phosphinic acid