(2S,3S)-2-[2-({[(benzyloxy)carbonyl]amino}ethanethioamido)-2-methylpropanamido]-3-methylpentanoic acid

Base Information

• Chemical Name: (2S,3S)-2-[2-({[(benzyloxy)carbonyl]amino}ethanethioamido)-2-methylpropanamido]-3-methylpentanoic acid
• CAS No.: 457058-53-6
• Molecular Formula: C₂₀H₂₉N₃O₅S
• Molecular Weight: 423.533
• Mol file: 457058-53-6.mol

Synonyms:(2S,3S)-2-[2-({[(benzyloxy)carbonyl]amino}ethanethioamido)-2-methylpropanamido]-3-methylpentanoic acid

Chemical Property of (2S,3S)-2-[2-({[(benzyloxy)carbonyl]amino}ethanethioamido)-2-methylpropanamido]-3-methylpentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-[2-({[(benzyloxy)carbonyl]amino}ethanethioamido)-2-methylpropanamido]-3-methylpentanoic acid

There total 4 articles about (2S,3S)-2-[2-({[(benzyloxy)carbonyl]amino}ethanethioamido)-2-methylpropanamido]-3-methylpentanoic 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%

methyl (2S,3S)-2-[2-({[(benzyloxy)carbonyl]amino}ethanethioamido)-2-methylpropanamido]-3-methylpentanoate (457058-63-8) → (2S,3S)-2-[2-({[(benzyloxy)carbonyl]amino}ethanethioamido)-2-methylpropanamido]-3-methylpentanoic acid (457058-53-6)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 4h;

DOI:10.1002/1522-2675(200204)85:4<990::AID-HLCA990>3.0.CO;2-6

Reference yield:

methyl L-isoleucinate hydrochloride (18598-74-8) → (2S,3S)-2-[2-({[(benzyloxy)carbonyl]amino}ethanethioamido)-2-methylpropanamido]-3-methylpentanoic acid (457058-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / EtN(i-Pr)2; 1-hydroxy-1H-benzotriazole / acetonitrile / 120 h / 20 °C

2: 100 percent / LiOH*H₂O / tetrahydrofuran; H₂O; methanol / 4 h / 20 °C

With lithium hydroxide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; water; acetonitrile;

DOI:10.1002/1522-2675(200204)85:4<990::AID-HLCA990>3.0.CO;2-6

Reference yield:

benzyl N-<2-<<1,1-dimethyl-2--2-oxoethyl>amino>-2-thioxoethyl>carbamate (238748-87-3) → (2S,3S)-2-[2-({[(benzyloxy)carbonyl]amino}ethanethioamido)-2-methylpropanamido]-3-methylpentanoic acid (457058-53-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / (+/-)-camphor-10-sulfonic acid / CH₂Cl₂ / 0.03 h / 20 °C

2: 74 percent / EtN(i-Pr)2; 1-hydroxy-1H-benzotriazole / acetonitrile / 120 h / 20 °C

3: 100 percent / LiOH*H₂O / tetrahydrofuran; H₂O; methanol / 4 h / 20 °C

With lithium hydroxide; camphor-10-sulfonic acid; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1002/1522-2675(200204)85:4<990::AID-HLCA990>3.0.CO;2-6

upstream raw materials:

methyl (2S,3S)-2-[2-({[(benzyloxy)carbonyl]amino}ethanethioamido)-2-methylpropanamido]-3-methylpentanoate

methyl L-isoleucinate hydrochloride

benzyl N-<2-<<1,1-dimethyl-2--2-oxoethyl>amino>-2-thioxoethyl>carbamate

benzyl N-[1-(4,5-dihydro-4,4-dimethyl-5-oxo-1,3-thiazol-2-yl)methyl]carbamate