allyl 2(S)-(acetylamino)-3-[[4(S)-[(2(R)-{[2(R,S)-hydroxy-3(S)-({[1-(allyloxycarbonyl)pyrrolidin-2(S)-yl]carbonyl}amino)-6-({[(tert-butyloxycarbonyl)imino][(tert-butyloxycarbonyl)amino]methyl}amino)hexanoyl]amino}-3-phenylpropanoyl)amino]-5-[4-(tert-...

Base Information

• Chemical Name: allyl 2(S)-(acetylamino)-3-[[4(S)-[(2(R)-{[2(R,S)-hydroxy-3(S)-({[1-(allyloxycarbonyl)pyrrolidin-2(S)-yl]carbonyl}amino)-6-({[(tert-butyloxycarbonyl)imino][(tert-butyloxycarbonyl)amino]methyl}amino)hexanoyl]amino}-3-phenylpropanoyl)amino]-5-[4-(tert-...
• CAS No.: 190203-27-1
• Molecular Formula: C₅₈H₈₃N₉O₁₅
• Molecular Weight: 1146.35
• Mol file: 190203-27-1.mol

Synonyms:allyl 2(S)-(acetylamino)-3-[[4(S)-[(2(R)-{[2(R,S)-hydroxy-3(S)-({[1-(allyloxycarbonyl)pyrrolidin-2(S)-yl]carbonyl}amino)-6-({[(tert-butyloxycarbonyl)imino][(tert-butyloxycarbonyl)amino]methyl}amino)hexanoyl]amino}-3-phenylpropanoyl)amino]-5-[4-(tert-...

Chemical Property of allyl 2(S)-(acetylamino)-3-[[4(S)-[(2(R)-{[2(R,S)-hydroxy-3(S)-({[1-(allyloxycarbonyl)pyrrolidin-2(S)-yl]carbonyl}amino)-6-({[(tert-butyloxycarbonyl)imino][(tert-butyloxycarbonyl)amino]methyl}amino)hexanoyl]amino}-3-phenylpropanoyl)amino]-5-[4-(tert-...

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2(S)-(acetylamino)-3-[[4(S)-[(2(R)-{[2(R,S)-hydroxy-3(S)-({[1-(allyloxycarbonyl)pyrrolidin-2(S)-yl]carbonyl}amino)-6-({[(tert-butyloxycarbonyl)imino][(tert-butyloxycarbonyl)amino]methyl}amino)hexanoyl]amino}-3-phenylpropanoyl)amino]-5-[4-(tert-...

There total 18 articles about allyl 2(S)-(acetylamino)-3-[[4(S)-[(2(R)-{[2(R,S)-hydroxy-3(S)-({[1-(allyloxycarbonyl)pyrrolidin-2(S)-yl]carbonyl}amino)-6-({[(tert-butyloxycarbonyl)imino][(tert-butyloxycarbonyl)amino]methyl}amino)hexanoyl]amino}-3-phenylpropanoyl)amino]-5-[4-(tert-... 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: 85.3%

(S)-2-Acetylamino-3-[(E)-(S)-4-amino-5-(4-tert-butoxy-phenyl)-pent-2-enoylamino]-propionic acid allyl ester (171109-56-1) + 2(R)-{[2(R,S)-hydroxy-3(S)-({[1-(allyloxycarbonyl)pyrrolidin-2(S)-yl]carbonyl}amino)-6-({[(tert-butyloxycarbonyl)imino][(tert-butyloxycarbonyl)amino]methyl}amino)hexanoyl]amino}-3-phenylpropanoic acid (190203-21-5) → allyl 2(S)-(acetylamino)-3-[[4(S)-[(2(R)-{[2(R,S)-hydroxy-3(S)-({[1-(allyloxycarbonyl)pyrrolidin-2(S)-yl]carbonyl}amino)-6-({[(tert-butyloxycarbonyl)imino][(tert-butyloxycarbonyl)amino]methyl}amino)hexanoyl]amino}-3-phenylpropanoyl)amino]-5-[4-(tert-... (190203-27-1)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1021/jo961447m

Reference yield:

L-ornithine (70-26-8,25104-12-5,410523-47-6) → allyl 2(S)-(acetylamino)-3-[[4(S)-[(2(R)-{[2(R,S)-hydroxy-3(S)-({[1-(allyloxycarbonyl)pyrrolidin-2(S)-yl]carbonyl}amino)-6-({[(tert-butyloxycarbonyl)imino][(tert-butyloxycarbonyl)amino]methyl}amino)hexanoyl]amino}-3-phenylpropanoyl)amino]-5-[4-(tert-... (190203-27-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) CuCO₃, 2.) DIPEA, 3.) EDTA, NaHCO₃ / 1.) H₂O, 100 deg C, 1 h, 2.) formamide, room temperature, 24 h, 3.) acetone, H₂O, room temperature, 12 h

2: 91 percent / CH₂Cl₂; ethanol / 0 °C

3: 97 percent / DIBALH / CH₂Cl₂; hexane / 1.25 h / -65 °C

4: 53.6 percent / n-BuLi / hexane; tetrahydrofuran / 5 h / -65 °C / 1.) 20 min, 2.) 5 h

5: 79 percent / HgCl₂, HgO / H₂O / 72 h / Ambient temperature

6: 96.4 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 0.2 h / Ambient temperature

7: 61.3 percent / HOBt, DCC, DIPEA / CH₂Cl₂ / 1.) 0 deg C, 45 min, 2.) 0 deg C, 30 min; 18 h

8: 100 percent / H₂ / Pd-C / methanol / 6 h

9: 79.1 percent / DIPEA, TBTU / CH₂Cl₂ / 2.5 h

10: 99.7 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 0.2 h

11: 85.3 percent / DIPEA, TBTU / CH₂Cl₂ / 3 h / Ambient temperature

With copper(II) carbonate; lithium hydroxide; n-butyllithium; ethylenediaminetetraacetic acid; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; mercury dichloride; mercury(II) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water;

DOI:10.1021/jo961447m

Reference yield:

methyl 2(S)-<(phenylmethoxycarbonyl)amino>-5-<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>pentanoate (145013-07-6) → allyl 2(S)-(acetylamino)-3-[[4(S)-[(2(R)-{[2(R,S)-hydroxy-3(S)-({[1-(allyloxycarbonyl)pyrrolidin-2(S)-yl]carbonyl}amino)-6-({[(tert-butyloxycarbonyl)imino][(tert-butyloxycarbonyl)amino]methyl}amino)hexanoyl]amino}-3-phenylpropanoyl)amino]-5-[4-(tert-... (190203-27-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 97 percent / DIBALH / CH₂Cl₂; hexane / 1.25 h / -65 °C

2: 53.6 percent / n-BuLi / hexane; tetrahydrofuran / 5 h / -65 °C / 1.) 20 min, 2.) 5 h

3: 79 percent / HgCl₂, HgO / H₂O / 72 h / Ambient temperature

4: 96.4 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 0.2 h / Ambient temperature

5: 61.3 percent / HOBt, DCC, DIPEA / CH₂Cl₂ / 1.) 0 deg C, 45 min, 2.) 0 deg C, 30 min; 18 h

6: 100 percent / H₂ / Pd-C / methanol / 6 h

7: 79.1 percent / DIPEA, TBTU / CH₂Cl₂ / 2.5 h

8: 99.7 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 0.2 h

9: 85.3 percent / DIPEA, TBTU / CH₂Cl₂ / 3 h / Ambient temperature

With lithium hydroxide; n-butyllithium; hydrogen; diisobutylaluminium hydride; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; mercury dichloride; mercury(II) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water;

DOI:10.1021/jo961447m

upstream raw materials:

(S)-2-Acetylamino-3-[(E)-(S)-4-amino-5-(4-tert-butoxy-phenyl)-pent-2-enoylamino]-propionic acid allyl ester

2(R)-{[2(R,S)-hydroxy-3(S)-({[1-(allyloxycarbonyl)pyrrolidin-2(S)-yl]carbonyl}amino)-6-({[(tert-butyloxycarbonyl)imino][(tert-butyloxycarbonyl)amino]methyl}amino)hexanoyl]amino}-3-phenylpropanoic acid

L-ornithine

(2S)-N-allyloxycarbonyl-L-proline

Downstream raw materials:

(2S,5S,11S,14R,17(R,S),18S)-N-<11-<4-(tert-butyloxy)benzyl>-14-benzyl-17-hydroxy-18-<<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>propyl>-4,8,13,16,20-pentaoxo-2,3,4,5,6,7,8,11,12,13,14,15,16,17,18,19,20,20a-octadeca...

(2S,5S,11S,14R,17(R,S),18S)-N-<11-<4-(tert-butyloxy)benzyl>-14-benzyl-17-hydroxy-18-<<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>propyl>-4,8,13,16,17,20-hexaoxo-2,3,4,5,6,7,8,11,12,13,14,15,16,17,18,19,20,20a-octadeca...

cyclotheonamide B