[3-((2S,8S,11R)-8-Allyl-11,14-dibenzyl-3,6,9,12,15-pentaoxo-14-trifluoromethyl-1,4,7,10,13-pentaaza-cyclopentadec-2-yl)-propyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [3-((2S,8S,11R)-8-Allyl-11,14-dibenzyl-3,6,9,12,15-pentaoxo-14-trifluoromethyl-1,4,7,10,13-pentaaza-cyclopentadec-2-yl)-propyl]-carbamic acid benzyl ester
• CAS No.: 653587-61-2
• Molecular Formula: C₃₉H₄₃F₃N₆O₇
• Molecular Weight: 764.802
• Mol file: 653587-61-2.mol

Synonyms:[3-((2S,8S,11R)-8-Allyl-11,14-dibenzyl-3,6,9,12,15-pentaoxo-14-trifluoromethyl-1,4,7,10,13-pentaaza-cyclopentadec-2-yl)-propyl]-carbamic acid benzyl ester

Chemical Property of [3-((2S,8S,11R)-8-Allyl-11,14-dibenzyl-3,6,9,12,15-pentaoxo-14-trifluoromethyl-1,4,7,10,13-pentaaza-cyclopentadec-2-yl)-propyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3-((2S,8S,11R)-8-Allyl-11,14-dibenzyl-3,6,9,12,15-pentaoxo-14-trifluoromethyl-1,4,7,10,13-pentaaza-cyclopentadec-2-yl)-propyl]-carbamic acid benzyl ester

There total 10 articles about [3-((2S,8S,11R)-8-Allyl-11,14-dibenzyl-3,6,9,12,15-pentaoxo-14-trifluoromethyl-1,4,7,10,13-pentaaza-cyclopentadec-2-yl)-propyl]-carbamic acid 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:

((S)-2-{2-[(R)-2-((S)-2-Amino-pent-4-enoylamino)-3-phenyl-propionylamino]-2-benzyl-3,3,3-trifluoro-propionylamino}-5-benzyloxycarbonylamino-pentanoylamino)-acetic acid (653587-60-1) → [3-((2S,8S,11R)-8-Allyl-11,14-dibenzyl-3,6,9,12,15-pentaoxo-14-trifluoromethyl-1,4,7,10,13-pentaaza-cyclopentadec-2-yl)-propyl]-carbamic acid benzyl ester (653587-61-2)

Guidance literature:

With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In acetonitrile; for 0.25h;

DOI:10.1021/jm0511334

Reference yield:

(R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionyl bromide (653587-69-0) → [3-((2S,8S,11R)-8-Allyl-11,14-dibenzyl-3,6,9,12,15-pentaoxo-14-trifluoromethyl-1,4,7,10,13-pentaaza-cyclopentadec-2-yl)-propyl]-carbamic acid benzyl ester (653587-61-2)

Guidance literature:

Multi-step reaction with 8 steps

1: CH₂Cl₂ / 3 h / 0 - 20 °C

2: BBr₃ / CH₂Cl₂ / 4 h / Heating

3: HATU; DIEA / acetonitrile / 1 h

4: NH₂NH₂*H₂O / ethanol / 1.5 h / Heating

5: HOBT; TBTU; DIEA / acetonitrile / 1 h

6: piperidine / CH₂Cl₂ / 2 h / 20 °C

7: TFA / CH₂Cl₂ / 1 h

8: HOBT; TBTU; DIEA / acetonitrile / 0.25 h

With piperidine; boron tribromide; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jm0511334

Reference yield:

2-benzyl-2-benzyloxycarbonylamino-3,3,3-trifluoro-propionic acid ethyl ester → [3-((2S,8S,11R)-8-Allyl-11,14-dibenzyl-3,6,9,12,15-pentaoxo-14-trifluoromethyl-1,4,7,10,13-pentaaza-cyclopentadec-2-yl)-propyl]-carbamic acid benzyl ester (653587-61-2)

Guidance literature:

Multi-step reaction with 8 steps

1: CH₂Cl₂ / 3 h / 0 - 20 °C

2: BBr₃ / CH₂Cl₂ / 4 h / Heating

3: HATU; DIEA / acetonitrile / 1 h

4: NH₂NH₂*H₂O / ethanol / 1.5 h / Heating

5: HOBT; TBTU; DIEA / acetonitrile / 1 h

6: piperidine / CH₂Cl₂ / 2 h / 20 °C

7: TFA / CH₂Cl₂ / 1 h

8: HOBT; TBTU; DIEA / acetonitrile / 0.25 h

With piperidine; boron tribromide; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jm0511334

upstream raw materials:

((S)-2-{2-[(R)-2-((S)-2-Amino-pent-4-enoylamino)-3-phenyl-propionylamino]-2-benzyl-3,3,3-trifluoro-propionylamino}-5-benzyloxycarbonylamino-pentanoylamino)-acetic acid

(R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionyl bromide

2-Benzyl-2-[(R)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionylamino]-3,3,3-trifluoro-propionic acid

2-Benzyl-2-[(R)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionylamino]-3,3,3-trifluoro-propionic acid ethyl ester

Downstream raw materials:

[(2S,5R,11S)-5,8-Dibenzyl-11-(3-benzyloxycarbonylamino-propyl)-3,6,9,12,15-pentaoxo-8-trifluoromethyl-1,4,7,10,13-pentaaza-cyclopentadec-2-yl]-acetic acid