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

Base Information

• Chemical Name: diphenylmethyl (2S,5R,6RS)-N-benzyloxycarbonyl-6-hydroxy-5-methyl-2-pipecolic acid
• CAS No.: 259151-26-3
• Molecular Formula: C₂₈H₂₉NO₅
• Molecular Weight: 459.542
• Mol file: 259151-26-3.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about diphenylmethyl (2S,5R,6RS)-N-benzyloxycarbonyl-6-hydroxy-5-methyl-2-pipecolic 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:

diphenylmethyl (2S)-N-benzyloxycarbonyl-5-methyl-6-oxopipecolate → diphenylmethyl (2S,5R,6RS)-N-benzyloxycarbonyl-6-hydroxy-5-methyl-2-pipecolic acid (259151-26-3)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; ethyl acetate; at 0 ℃; for 2h;

DOI:10.1248/cpb.47.1532

Reference yield:

diphenylmethyl (2S)-N-benzyloxycarbonyl-6-oxopipecolate (216301-91-6) → diphenylmethyl (2S,5R,6RS)-N-benzyloxycarbonyl-6-hydroxy-5-methyl-2-pipecolic acid (259151-26-3)

Guidance literature:

Multi-step reaction with 2 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

With lithium tri-t-butoxyaluminum hydride; lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Methylation / 2.1: Reduction;

DOI:10.1248/cpb.47.1532

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

upstream raw materials:

diphenylmethyl (2S)-N-benzyloxycarbonyl-6-oxopipecolate

Downstream raw materials:

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

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