methyl (2RS,4R)-2-[(1R,4S)-4-diphenylmethoxycarbonyl-4-benzyloxycarbonylamino-1-methylbutyl]thiazolidine-4-carboxylate

Base Information

• Chemical Name: methyl (2RS,4R)-2-[(1R,4S)-4-diphenylmethoxycarbonyl-4-benzyloxycarbonylamino-1-methylbutyl]thiazolidine-4-carboxylate
• CAS No.: 216302-09-9
• Molecular Formula: C₃₂H₃₆N₂O₆S
• Molecular Weight: 576.714
• Mol file: 216302-09-9.mol

Synonyms:

Chemical Property of methyl (2RS,4R)-2-[(1R,4S)-4-diphenylmethoxycarbonyl-4-benzyloxycarbonylamino-1-methylbutyl]thiazolidine-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2RS,4R)-2-[(1R,4S)-4-diphenylmethoxycarbonyl-4-benzyloxycarbonylamino-1-methylbutyl]thiazolidine-4-carboxylate

There total 5 articles about methyl (2RS,4R)-2-[(1R,4S)-4-diphenylmethoxycarbonyl-4-benzyloxycarbonylamino-1-methylbutyl]thiazolidine-4-carboxylate 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-cysteine methyl ester hydrochloride (18598-63-5) + diphenylmethyl (2S,5R,6RS)-N-benzyloxycarbonyl-6-hydroxy-5-methyl-2-pipecolic acid (259151-26-3) → methyl (2RS,4R)-2-[(1R,4S)-4-diphenylmethoxycarbonyl-4-benzyloxycarbonylamino-1-methylbutyl]thiazolidine-4-carboxylate (216302-09-9)

Guidance literature:

With sodium acetate; acetic acid; In methanol; ethanol; water; at 20 ℃; for 18h;

DOI:10.1248/cpb.47.1532

Reference yield:

L-Cysteine methyl ester (2485-62-3) + diphenylmethyl (2S,5S,6RS)-N-benzyloxycarbonyl-6-hydroxy-5-methyl-2-pipecolic acid (259151-28-5) → methyl (2RS,4R)-2-[(1S,4S)-4-diphenylmethoxycarbonyl-4-benzyloxycarbonylamino-1-methylbutyl]thiazolidine-4-carboxylate + methyl (2RS,4R)-2-[(1R,4S)-4-diphenylmethoxycarbonyl-4-benzyloxycarbonylamino-1-methylbutyl]thiazolidine-4-carboxylate (216302-09-9)

Guidance literature:

With sodium acetate; acetic acid; In methanol; ethanol; water; at 20 ℃; for 16h; Title compound not separated from byproducts;

DOI:10.1248/cpb.47.1532

Reference yield:

diphenylmethyl (2S)-N-benzyloxycarbonyl-6-oxopipecolate (216301-91-6) → methyl (2RS,4R)-2-[(1R,4S)-4-diphenylmethoxycarbonyl-4-benzyloxycarbonylamino-1-methylbutyl]thiazolidine-4-carboxylate (216302-09-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiHMDS / tetrahydrofuran; dimethylformamide / 0.5 h

1.2: 100 g / tetrahydrofuran; dimethylformamide / 3 h

2.1: LiAlH(t-BuO)3 / tetrahydrofuran; ethyl acetate / 2 h / 0 °C

3.1: AcONa; AcOH / ethanol; methanol; H₂O / 18 h / 20 °C

With sodium acetate; acetic acid; lithium tri-t-butoxyaluminum hydride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Methylation / 2.1: Reduction / 3.1: Condensation;

DOI:10.1248/cpb.47.1532

upstream raw materials:

L-Cysteine methyl ester

diphenylmethyl (2S,5S,6RS)-N-benzyloxycarbonyl-6-hydroxy-5-methyl-2-pipecolic acid

L-cysteine methyl ester hydrochloride

diphenylmethyl (2S,5R,6RS)-N-benzyloxycarbonyl-6-hydroxy-5-methyl-2-pipecolic acid

Downstream raw materials:

methyl (3R,6S,9R,9aR)-6-benzyloxycarbonylamino-9-methyl-5-oxooctahydroazepine[2,1-b]thiazole-3-carboxylate

methyl (2RS,4R)-2-[(1R,4R)-4-benzyloxycarbonylamino-4-carboxy-1-methylbutyl]thiazolidine-4-carboxylate