dimethyl (R)-(+)-1-diazo-2-oxo-4-(tert-butoxycarbonylamino)-4-phenylbutylphosphonate

Base Information

Chemical Name:dimethyl (R)-(+)-1-diazo-2-oxo-4-(tert-butoxycarbonylamino)-4-phenylbutylphosphonate
CAS No.:814256-40-1
Molecular Formula:C₁₇H₂₄N₃O₆P
Molecular Weight:397.368
Hs Code.:

Synonyms:dimethyl (R)-(+)-1-diazo-2-oxo-4-(tert-butoxycarbonylamino)-4-phenylbutylphosphonate

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Chemical Property of dimethyl (R)-(+)-1-diazo-2-oxo-4-(tert-butoxycarbonylamino)-4-phenylbutylphosphonate

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Technology Process of dimethyl (R)-(+)-1-diazo-2-oxo-4-(tert-butoxycarbonylamino)-4-phenylbutylphosphonate

There total 4 articles about dimethyl (R)-(+)-1-diazo-2-oxo-4-(tert-butoxycarbonylamino)-4-phenylbutylphosphonate 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: 83.0%

: 814256-35-4
dimethyl (R)-(-)-2-oxo-4-(tert-butoxycarbonylamino)-4-phenylbutylphosphonate

: 814256-40-1
dimethyl (R)-(+)-1-diazo-2-oxo-4-(tert-butoxycarbonylamino)-4-phenylbutylphosphonate

Guidance literature:: With 4-acetamidobenzenesulfonyl azide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/ol048157+

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 814256-40-1
dimethyl (R)-(+)-1-diazo-2-oxo-4-(tert-butoxycarbonylamino)-4-phenylbutylphosphonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: TFA / methanol / 0 - 20 °C

1.2: 90 percent / NEt₃; DMAP / tetrahydrofuran / 3 h / 0 °C

2.1: 83 percent / NaH; 4-acetamidobenzenesulfonyl azide / tetrahydrofuran / 1 h / 20 °C

With 4-acetamidobenzenesulfonyl azide; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; methanol;
DOI:10.1021/ol048157+

Reference yield:

: 158009-86-0
(S_S,3R)-(+)-methyl 3-[N-(p-toluenesulfinyl)amino]-3-(phenyl)propanoate

: 814256-40-1
dimethyl (R)-(+)-1-diazo-2-oxo-4-(tert-butoxycarbonylamino)-4-phenylbutylphosphonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; cyclohexane / 0.25 h / -78 °C

1.2: 84 percent / tetrahydrofuran; cyclohexane / 2 h / -78 °C

2.1: TFA / methanol / 0 - 20 °C

2.2: 90 percent / NEt₃; DMAP / tetrahydrofuran / 3 h / 0 °C

3.1: 83 percent / NaH; 4-acetamidobenzenesulfonyl azide / tetrahydrofuran / 1 h / 20 °C

With n-butyllithium; 4-acetamidobenzenesulfonyl azide; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; methanol; cyclohexane;
DOI:10.1021/ol048157+