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

Base Information

• Chemical Name: (R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid
• CAS No.: 166169-44-4
• Molecular Formula: C₅₀H₅₅N₃O₇S
• Molecular Weight: 842.069

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic 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: 100.0%

(R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid methyl ester (166169-43-3) → (R*)-N-amino>-3-<(triphenylmethyl)thio>propyl>-N-(benzyloxycarbonyl)-L-valyl>-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid (166169-44-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; for 16h; Ambient temperature;

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 (166169-44-4)

Guidance literature:

Multi-step reaction with 5 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

5: 100 percent / 1 N LiOH / tetrahydrofuran; methanol / 16 h / Ambient temperature

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 (166169-44-4)

Guidance literature:

Multi-step reaction with 5 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

5: 100 percent / 1 N LiOH / tetrahydrofuran; methanol / 16 h / Ambient temperature

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:

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

L-valine methylester hydrochloride

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

N-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<(triphenylmethyl)thio>propyl>carbonyl>-L-valine methyl ester

Downstream raw materials:

(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 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]-succinamic acid methyl ester

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

(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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