methyl 2(R)-<<2(R,S)-hydroxy-3(S)-<(phenylmethoxycarbonyl)amino>-6-<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>hexanoyl>amino>-3-phenylpropanoate

Base Information

• Chemical Name: methyl 2(R)-<<2(R,S)-hydroxy-3(S)-<(phenylmethoxycarbonyl)amino>-6-<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>hexanoyl>amino>-3-phenylpropanoate
• CAS No.: 190203-18-0
• Molecular Formula: C₃₅H₄₉N₅O₁₀
• Molecular Weight: 699.802
• Mol file: 190203-18-0.mol

Synonyms:methyl 2(R)-<<2(R,S)-hydroxy-3(S)-<(phenylmethoxycarbonyl)amino>-6-<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>hexanoyl>amino>-3-phenylpropanoate

Chemical Property of methyl 2(R)-<<2(R,S)-hydroxy-3(S)-<(phenylmethoxycarbonyl)amino>-6-<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>hexanoyl>amino>-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2(R)-<<2(R,S)-hydroxy-3(S)-<(phenylmethoxycarbonyl)amino>-6-<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>hexanoyl>amino>-3-phenylpropanoate

There total 10 articles about methyl 2(R)-<<2(R,S)-hydroxy-3(S)-<(phenylmethoxycarbonyl)amino>-6-<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>hexanoyl>amino>-3-phenylpropanoate 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: 61.3%

D-phenylalanine methyl ester hydrochloride (13033-84-6) + 2(R,S)-hydroxy-3(S)-<(phenylmethoxycarbonyl)amino>-6-<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>hexanoic acid (190203-17-9) → methyl 2(R)-<<2(R,S)-hydroxy-3(S)-<(phenylmethoxycarbonyl)amino>-6-<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>hexanoyl>amino>-3-phenylpropanoate (190203-18-0)

Guidance literature:

With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane; 1.) 0 deg C, 45 min, 2.) 0 deg C, 30 min; 18 h;

DOI:10.1021/jo961447m

Reference yield:

L-ornithine (70-26-8,25104-12-5,410523-47-6) → methyl 2(R)-<<2(R,S)-hydroxy-3(S)-<(phenylmethoxycarbonyl)amino>-6-<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>hexanoyl>amino>-3-phenylpropanoate (190203-18-0)

Guidance literature:

Multi-step reaction with 7 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

With copper(II) carbonate; lithium hydroxide; n-butyllithium; ethylenediaminetetraacetic acid; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water;

DOI:10.1021/jo961447m

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → methyl 2(R)-<<2(R,S)-hydroxy-3(S)-<(phenylmethoxycarbonyl)amino>-6-<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>hexanoyl>amino>-3-phenylpropanoate (190203-18-0)

Guidance literature:

Multi-step reaction with 7 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

With copper(II) carbonate; lithium hydroxide; n-butyllithium; ethylenediaminetetraacetic acid; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water;

DOI:10.1021/jo961447m

upstream raw materials:

D-phenylalanine methyl ester

2(R,S)-hydroxy-3(S)-<(phenylmethoxycarbonyl)amino>-6-<<<(tert-butyloxycarbonyl)imino><(tert-butyloxycarbonyl)amino>methyl>amino>hexanoic acid

D-phenylalanine methyl ester hydrochloride

L-ornithine

Downstream raw materials:

cyclotheonamide B

(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...

(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...

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