(S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid

Base Information

• Chemical Name: (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid
• CAS No.: 176752-39-9
• Molecular Formula: C₄₃H₅₀N₁₀O₇
• Molecular Weight: 818.933

Synonyms:(S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid

Chemical Property of (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid

Chemical Property:

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Technology Process of (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid

There total 11 articles about (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid 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: 80.0%

(S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester (176752-38-8) → (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid (176752-39-9)

Guidance literature:

With lithium hydroxide; In methanol; at 4 ℃; for 3.5h;

DOI:10.1016/0968-0896(95)00183-2

Reference yield:

trityl chloride (76-83-5) → (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid (176752-39-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / Et₃N / benzene / 1 h / 80 °C

2: 0.78 g / H₂ / 10percent Pd/C / methanol / 2.5 h / 25 °C / 760 Torr

3: methanol / 1.5 h / 25 °C

4: NaBH₄ / methanol / 0.5 h / 5 - 10 °C

5: 61 percent / NaBH₃CN, aq. AcOH / acetonitrile / 0.33 h / 25 °C

6: 38 percent / H₂ / 10percent Pd/C / methanol / 10 h / 25 °C / 760 Torr

7: 45 percent / BOPCl, Et₃N / CH₂Cl₂ / 6 h / 25 °C

8: 80 percent / 0.1N aq. LiOH / methanol / 3.5 h / 4 °C

With lithium hydroxide; sodium tetrahydroborate; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium cyanoborohydride; acetic acid; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile; benzene;

DOI:10.1016/0968-0896(95)00183-2

Reference yield:

1,Nα-bis-benzyloxycarbonyl-histidine methyl ester (40917-50-8) → (S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid (176752-39-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / 1N aq. NaOH / methanol / 0.01 h / -20 °C

2: 99 percent / Et₃N / benzene / 1 h / 80 °C

3: 0.78 g / H₂ / 10percent Pd/C / methanol / 2.5 h / 25 °C / 760 Torr

4: methanol / 1.5 h / 25 °C

5: NaBH₄ / methanol / 0.5 h / 5 - 10 °C

6: 61 percent / NaBH₃CN, aq. AcOH / acetonitrile / 0.33 h / 25 °C

7: 38 percent / H₂ / 10percent Pd/C / methanol / 10 h / 25 °C / 760 Torr

8: 45 percent / BOPCl, Et₃N / CH₂Cl₂ / 6 h / 25 °C

9: 80 percent / 0.1N aq. LiOH / methanol / 3.5 h / 4 °C

With lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium cyanoborohydride; acetic acid; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile; benzene;

DOI:10.1016/0968-0896(95)00183-2

upstream raw materials:

(S)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-methyl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester

trityl chloride

1,N^α-bis-benzyloxycarbonyl-histidine methyl ester

N^im-triphenylmethyl-L-histidine methyl ester

Downstream raw materials:

N^α-[(tert-butyloxy)carbonyl]-N^β-[3(S)-[4-amino-6-[[[methyl-N-1-(S)-(((4(S)-[({1(S)-[({2-[4'-({[3-(dimethylsulfonio)-1-propyl]amino}carbonyl)-2',4-bithiazol-2-yl]-1-ethyl}amino)carbonyl]-2(R)-hydroxy-1-propyl}amino)carbonyl]-3(S)-hydroxy-2(R)-pe...

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