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

Base Information

• Chemical Name: 1-benzyl 2-methyl (2S)-5-((1-adamantyloxy){2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphoryl)tetrahydro-1H-pyrrole-1,2-dicarboxylate
• CAS No.: 952703-85-4
• Molecular Formula: C₃₈H₄₄NO₉P
• Molecular Weight: 689.742
• Mol file: 952703-85-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 1-benzyl 2-methyl (2S)-5-((1-adamantyloxy){2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphoryl)tetrahydro-1H-pyrrole-1,2-dicarboxylate 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: 44.0%

1-Adamantyl bromide (768-90-1) + (2S)-1-[(benzyloxy)carbonyl]-5-(methoxycarbonyl)tetrahydro-1H-pyrrol-2-yl{2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphinic acid (952661-10-8) → 1-benzyl 2-methyl (2S)-5-((1-adamantyloxy){2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphoryl)tetrahydro-1H-pyrrole-1,2-dicarboxylate (952703-85-4)

Guidance literature:

With silver(l) oxide; In chloroform; for 3h; Heating;

DOI:10.1021/jo071081l

Reference yield:

2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynylphosphinic acid (952661-08-4) → 1-benzyl 2-methyl (2S)-5-((1-adamantyloxy){2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphoryl)tetrahydro-1H-pyrrole-1,2-dicarboxylate (952703-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TFA; AcOH / 0.5 h / 20 °C

1.2: 41 percent / AcCl; AcOH; TFA / 5 h / 20 °C

2.1: 44 percent / Ag₂O / CHCl₃ / 3 h / Heating

With acetic acid; trifluoroacetic acid; silver(l) oxide; In chloroform;

DOI:10.1021/jo071081l

Reference yield:

methyl (2S)-2-{[(benzyloxy)carbonyl](tert-butoxycarbonyl)amino}-5-oxopentanoate (952661-09-5) → 1-benzyl 2-methyl (2S)-5-((1-adamantyloxy){2-[(2-oxo-2-phenylethoxy)carbonyl]-4-pentynyl}phosphoryl)tetrahydro-1H-pyrrole-1,2-dicarboxylate (952703-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TFA; AcOH / 0.5 h / 20 °C

1.2: 41 percent / AcCl; AcOH; TFA / 5 h / 20 °C

2.1: 44 percent / Ag₂O / CHCl₃ / 3 h / Heating

With acetic acid; trifluoroacetic acid; silver(l) oxide; In chloroform;

DOI:10.1021/jo071081l

upstream raw materials:

1-Adamantyl bromide

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

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

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