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

Base Information

• Chemical Name: N-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<(triphenylmethyl)thio>propyl>carbonyl>-L-valine methyl ester
• CAS No.: 166169-40-0
• Molecular Formula: C₃₃H₄₂N₂O₄S
• Molecular Weight: 562.773
• Mol file: 166169-40-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about N-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<(triphenylmethyl)thio>propyl>carbonyl>-L-valine 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:

L-valine methylester hydrochloride (6306-52-1) + N-α-(tert-butoxycarbonyl)-S-(triphenylmethyl)-L-cysteinal (149910-63-4) → N-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<(triphenylmethyl)thio>propyl>carbonyl>-L-valine methyl ester (166169-40-0)

Guidance literature:

With sodium cyanoborohydride; acetic acid; Yield given. Multistep reaction; 1.) MeOH, RT, 30 min, 2.) MeOH, THF, RT, 2 h;

DOI:10.1021/jm950642a

Reference yield: 92.0%

benzyl chloroformate (501-53-1,94274-21-2) + N-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<(triphenylmethyl)thio>propyl>carbonyl>-L-valine methyl ester (166169-40-0) → (R*)-N-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<(triphenylmethyl)thio>propyl>carbonyl>-N-(benzyloxycarbonyl)-L-valine methyl ester (166169-41-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 16h;

DOI:10.1021/jm950642a

Reference yield:

N-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<(triphenylmethyl)thio>propyl>carbonyl>-L-valine methyl ester (166169-40-0) → (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

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / diisopropylethylamine / CH₂Cl₂ / 16 h / 0 - 20 °C

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

3: 72 percent / N,N-diisopropylethylamine, Bop-Cl / CH₂Cl₂ / 16 h / 0 °C

4: 100 percent / 1 N LiOH / tetrahydrofuran; methanol / 16 h / Ambient temperature

5: N,N-diisopropylethylamine, Bop / acetonitrile; dimethylformamide / 16 h

6: 2 N LiOH / tetrahydrofuran / 4 h / Ambient temperature

With lithium hydroxide; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm950642a

upstream raw materials:

L-valine methylester hydrochloride

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

Downstream raw materials:

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

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

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

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