(R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid methyl ester
• CAS No.: 166169-43-3
• Molecular Formula: C₅₁H₅₇N₃O₇S
• Molecular Weight: 856.095

Synonyms:(R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid methyl ester

Chemical Property of (R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid methyl ester

There total 4 articles about (R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 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: 72.0%

(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester, hydrochloride (78183-55-8) + (R*)-N-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<(triphenylmethyl)thio>propyl>carbonyl>-N-(benzyloxycarbonyl)-L-valine (166169-42-2) → (R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid methyl ester (166169-43-3)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 16h;

DOI:10.1021/jm950642a

Reference yield:

L-valine methylester hydrochloride (6306-52-1) → (R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid methyl ester (166169-43-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) acetic acid, 2.) NaBH₃CN / 1.) MeOH, RT, 30 min, 2.) MeOH, THF, RT, 2 h

2: 92 percent / diisopropylethylamine / CH₂Cl₂ / 16 h / 0 - 20 °C

3: 100 percent / 2 N LiOH / tetrahydrofuran; methanol / 16 h / Ambient temperature

4: 72 percent / N,N-diisopropylethylamine, Bop-Cl / CH₂Cl₂ / 16 h / 0 °C

With lithium hydroxide; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium cyanoborohydride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm950642a

Reference yield:

N-α-(tert-butoxycarbonyl)-S-(triphenylmethyl)-L-cysteinal (149910-63-4) → (R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid methyl ester (166169-43-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) acetic acid, 2.) NaBH₃CN / 1.) MeOH, RT, 30 min, 2.) MeOH, THF, RT, 2 h

2: 92 percent / diisopropylethylamine / CH₂Cl₂ / 16 h / 0 - 20 °C

3: 100 percent / 2 N LiOH / tetrahydrofuran; methanol / 16 h / Ambient temperature

4: 72 percent / N,N-diisopropylethylamine, Bop-Cl / CH₂Cl₂ / 16 h / 0 °C

With lithium hydroxide; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium cyanoborohydride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm950642a

upstream raw materials:

(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester, hydrochloride

(R*)-N-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<(triphenylmethyl)thio>propyl>carbonyl>-N-(benzyloxycarbonyl)-L-valine

L-valine methylester hydrochloride

N-α-(tert-butoxycarbonyl)-S-(triphenylmethyl)-L-cysteinal

Downstream raw materials:

(R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid

(S*,R*)-N-<<2-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydro-3-isoquinolinyl>carbonyl>-L-norleucine

(S*,R*)-N-<<2-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydro-3-isoquinolinyl>carbonyl>-L-norleucine methyl ester

(S)-2-[((S)-2-{(S)-2-[Benzyloxycarbonyl-((R)-2-tert-butoxycarbonylamino-3-tritylsulfanyl-propyl)-amino]-3-methyl-butyryl}-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl)-amino]-4-carbamoyl-butyric acid

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