(2S)-1-[(benzyloxy)carbonyl]-5-(methoxycarbonyl)tetrahydro-1H-pyrrol-2-yl{2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphinic acid

Base Information

• Chemical Name: (2S)-1-[(benzyloxy)carbonyl]-5-(methoxycarbonyl)tetrahydro-1H-pyrrol-2-yl{2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphinic acid
• CAS No.: 952661-10-8
• Molecular Formula: C₂₈H₃₀NO₉P
• Molecular Weight: 555.521
• Mol file: 952661-10-8.mol

Synonyms:

Chemical Property of (2S)-1-[(benzyloxy)carbonyl]-5-(methoxycarbonyl)tetrahydro-1H-pyrrol-2-yl{2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphinic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-1-[(benzyloxy)carbonyl]-5-(methoxycarbonyl)tetrahydro-1H-pyrrol-2-yl{2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphinic acid

There total 5 articles about (2S)-1-[(benzyloxy)carbonyl]-5-(methoxycarbonyl)tetrahydro-1H-pyrrol-2-yl{2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}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: 41.0%

2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynylphosphinic acid (952661-08-4) + methyl (2S)-2-{[(benzyloxy)carbonyl](tert-butoxycarbonyl)amino}-5-oxopentanoate (952661-09-5) → (2S)-1-[(benzyloxy)carbonyl]-5-(methoxycarbonyl)tetrahydro-1H-pyrrol-2-yl{2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphinic acid (952661-10-8)

Guidance literature:

methyl (2S)-2-{[(benzyloxy)carbonyl](tert-butoxycarbonyl)amino}-5-oxopentanoate; With acetic acid; trifluoroacetic acid; at 20 ℃; for 0.5h;

2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynylphosphinic acid; With acetic acid; acetyl chloride; trifluoroacetic acid; at 20 ℃; for 5h; Further stages.;

DOI:10.1021/jo071081l

Reference yield:

C6H9PO4 → (2S)-1-[(benzyloxy)carbonyl]-5-(methoxycarbonyl)tetrahydro-1H-pyrrol-2-yl{2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphinic acid (952661-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 55 percent / Et₃N / ethyl acetate / 6 h / 20 °C

2.1: TFA; AcOH / 0.5 h / 20 °C

2.2: 41 percent / AcCl; AcOH; TFA / 5 h / 20 °C

With acetic acid; triethylamine; trifluoroacetic acid; In ethyl acetate;

DOI:10.1021/jo071081l

Reference yield:

dimethyl (S)-N-(benzyloxycarbonyl)glutamate (67436-17-3) → (2S)-1-[(benzyloxy)carbonyl]-5-(methoxycarbonyl)tetrahydro-1H-pyrrol-2-yl{2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphinic acid (952661-10-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DMAP / 4 h / 20 °C

2.1: 1.22 g / DIBAL-H / diethyl ether; CH₂Cl₂ / 0.17 h / -78 °C

3.1: TFA; AcOH / 0.5 h / 20 °C

3.2: 41 percent / AcCl; AcOH; TFA / 5 h / 20 °C

With dmap; diisobutylaluminium hydride; acetic acid; trifluoroacetic acid; In diethyl ether; dichloromethane;

DOI:10.1021/jo071081l

upstream raw materials:

2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynylphosphinic acid

methyl (2S)-2-{[(benzyloxy)carbonyl](tert-butoxycarbonyl)amino}-5-oxopentanoate

dimethyl (S)-N-(benzyloxycarbonyl)glutamate

α-bromoacetophenone

Downstream raw materials:

1-benzyl 2-methyl (2S)-5-((1-adamantyloxy){2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphoryl)tetrahydro-1H-pyrrole-1,2-dicarboxylate