methyl (R)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridinyl>carbonyl>-erythro-β-tert-butoxy-L-histydyl>amino>pentanoate

Base Information

• Chemical Name: methyl (R)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridinyl>carbonyl>-erythro-β-tert-butoxy-L-histydyl>amino>pentanoate
• CAS No.: 124020-64-0
• Molecular Formula: C₃₉H₄₈N₁₀O₁₁S₂
• Molecular Weight: 897.003
• Mol file: 124020-64-0.mol

Synonyms:methyl (R)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridinyl>carbonyl>-erythro-β-tert-butoxy-L-histydyl>amino>pentanoate

Chemical Property of methyl (R)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridinyl>carbonyl>-erythro-β-tert-butoxy-L-histydyl>amino>pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (R)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridinyl>carbonyl>-erythro-β-tert-butoxy-L-histydyl>amino>pentanoate

There total 14 articles about methyl (R)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridinyl>carbonyl>-erythro-β-tert-butoxy-L-histydyl>amino>pentanoate 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)-Pyroglutaminol (17342-08-4) → methyl (R)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridinyl>carbonyl>-erythro-β-tert-butoxy-L-histydyl>amino>pentanoate (124020-64-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 72.8 percent / CBr₄, Ph₃P / acetonitrile / Ambient temperature

2: 91.7 percent / tributyltin hydride, AIBN / toluene / 5 h / 80 °C

3: 90.6 percent / 6 N HCl / 8 h / Heating

4: 100 percent / thionyl chloride / 72 h / Ambient temperature

5: 67 percent / HOBt*H₂O, DDC, Et₃N / CH₂Cl₂ / Ambient temperature

6: trifluoroacetic acid / 1.) 0 deg C, 10 min, 2.) RT, 1 h

7: CH₂Cl₂ / 3 h

8: 82 percent / H₂SO₄ / CH₂Cl₂ / 264 h / Ambient temperature

9: 1.) HCO₂H, 2.) 0.2 N HCl / 1.) Pd-black / 1.) RT, 1,5 h, methanol

10: diphenyl phosphoroazidate, Et₃N / dimethylformamide / Ambient temperature

With hydrogenchloride; formic acid; thionyl chloride; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; sulfuric acid; diphenyl phosphoryl azide; tri-n-butyl-tin hydride; benzotriazol-1-ol; triethylamine; triphenylphosphine; 2`,3`-dideoxycytidine; trifluoroacetic acid; palladium; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja00158a052

Reference yield:

erythro-β-hydroxy-L-histidine hydrate (41215-80-9) → methyl (R)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridinyl>carbonyl>-erythro-β-tert-butoxy-L-histydyl>amino>pentanoate (124020-64-0)

Guidance literature:

Multi-step reaction with 7 steps

1: Na₂SO₄ / H₂O; dioxane / Ambient temperature

2: 67 percent / HOBt*H₂O, DDC, Et₃N / CH₂Cl₂ / Ambient temperature

3: trifluoroacetic acid / 1.) 0 deg C, 10 min, 2.) RT, 1 h

4: CH₂Cl₂ / 3 h

5: 82 percent / H₂SO₄ / CH₂Cl₂ / 264 h / Ambient temperature

6: 1.) HCO₂H, 2.) 0.2 N HCl / 1.) Pd-black / 1.) RT, 1,5 h, methanol

7: diphenyl phosphoroazidate, Et₃N / dimethylformamide / Ambient temperature

With hydrogenchloride; formic acid; sulfuric acid; diphenyl phosphoryl azide; benzotriazol-1-ol; sodium sulfate; triethylamine; 2`,3`-dideoxycytidine; trifluoroacetic acid; palladium; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00158a052

Reference yield:

(R)-4-[(2S,3R)-2-Amino-3-hydroxy-3-(1H-imidazol-4-yl)-propionylamino]-pentanoic acid methyl ester → methyl (R)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridinyl>carbonyl>-erythro-β-tert-butoxy-L-histydyl>amino>pentanoate (124020-64-0)

Guidance literature:

Multi-step reaction with 4 steps

1: CH₂Cl₂ / 3 h

2: 82 percent / H₂SO₄ / CH₂Cl₂ / 264 h / Ambient temperature

3: 1.) HCO₂H, 2.) 0.2 N HCl / 1.) Pd-black / 1.) RT, 1,5 h, methanol

4: diphenyl phosphoroazidate, Et₃N / dimethylformamide / Ambient temperature

With hydrogenchloride; formic acid; sulfuric acid; diphenyl phosphoryl azide; triethylamine; palladium; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00158a052

upstream raw materials:

(R)-4-[(2S,3R)-2-Amino-3-tert-butoxy-3-(1H-imidazol-4-yl)-propionylamino]-pentanoic acid methyl ester; hydrochloride

6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-methoxypyridine-2-carboxylic acid

erythro-β-hydroxy-L-histidine hydrate

N^α,N^im-bis(tert-butoxycarbonyl)-erythro-β-hydroxy-L-histidine

Downstream raw materials:

(R)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridinyl>carbonyl>-erythro-β-tert-butoxy-L-histydyl>amino>pentanoic acid