N-<2(S)-ethylsulfonyl-3-(1-naphthyl)propionyl>-(N^im-trityl)-L-histidine methyl ester

Base Information

• Chemical Name: N-<2(S)-ethylsulfonyl-3-(1-naphthyl)propionyl>-(N^im-trityl)-L-histidine methyl ester
• CAS No.: 147875-08-9
• Molecular Formula: C₄₂H₄₁N₃O₅S
• Molecular Weight: 699.871

Synonyms:N-<2(S)-ethylsulfonyl-3-(1-naphthyl)propionyl>-(N^im-trityl)-L-histidine methyl ester

Chemical Property of N-<2(S)-ethylsulfonyl-3-(1-naphthyl)propionyl>-(N^im-trityl)-L-histidine methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of N-<2(S)-ethylsulfonyl-3-(1-naphthyl)propionyl>-(N^im-trityl)-L-histidine methyl ester

There total 9 articles about N-<2(S)-ethylsulfonyl-3-(1-naphthyl)propionyl>-(N^im-trityl)-L-histidine methyl 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-((S)-2-Ethylsulfanylmethyl-3-naphthalen-1-yl-propionylamino)-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester → N-<2(S)-ethylsulfonyl-3-(1-naphthyl)propionyl>-(Nim-trityl)-L-histidine methyl ester (147875-08-9)

Guidance literature:

With sodium tungstate; dihydrogen peroxide; In methanol; Yield given; Ambient temperature;

DOI:10.1248/cpb.40.3214

Reference yield:

(2S)-2-(1-naphthyl)methyl-1-O-methoxymethyl-1,3-propanediol (128349-91-7) → N-<2(S)-ethylsulfonyl-3-(1-naphthyl)propionyl>-(Nim-trityl)-L-histidine methyl ester (147875-08-9)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. H₂SO₄, CrO₃ / acetone / 2 h / 0 °C

2: aq. HCl / tetrahydrofuran / 1.5 h / 50 °C

3: 93.8 percent / hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / dimethylformamide / -5 - 5 °C

4: 83.1 percent / pyridine / Ambient temperature

5: NaH / dimethylformamide / 1 h / Ambient temperature

6: 30percent aq. H₂O₂, Na₂WO₄ / methanol / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; sodium tungstate; sulfuric acid; dihydrogen peroxide; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.40.3214

Reference yield:

1,3-dihydroxy-2-(1-naphthylmethyl)propane (59822-74-1) → N-<2(S)-ethylsulfonyl-3-(1-naphthyl)propionyl>-(Nim-trityl)-L-histidine methyl ester (147875-08-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 93.1 percent / 8.5 h / 8 - 30 °C / lipase P

2: diisopropylethylamine / CH₂Cl₂ / Ambient temperature

3: K₂CO₃, water / methanol / 48 h / Ambient temperature

4: aq. H₂SO₄, CrO₃ / acetone / 2 h / 0 °C

5: aq. HCl / tetrahydrofuran / 1.5 h / 50 °C

6: 93.8 percent / hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC) / dimethylformamide / -5 - 5 °C

7: 83.1 percent / pyridine / Ambient temperature

8: NaH / dimethylformamide / 1 h / Ambient temperature

9: 30percent aq. H₂O₂, Na₂WO₄ / methanol / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; sodium tungstate; sulfuric acid; water; dihydrogen peroxide; sodium hydride; potassium carbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.40.3214

upstream raw materials:

1,3-dihydroxy-2-(1-naphthylmethyl)propane

(2S)-2-(1-naphthyl)methyl-1-O-methoxymethyl-1,3-propanediol

(2R)-2-(1-naphthyl)methyl-1,3-propanediol-1-acetate

(R)-2-Methoxymethoxymethyl-3-naphthalen-1-yl-propionic acid

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