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

Base Information

Chemical Name:methyl (2RS,4R)-2-[(1R,4R)-4-benzyloxycarbonylamino-4-carboxy-1-methylbutyl]thiazolidine-4-carboxylate
CAS No.:216302-15-7
Molecular Formula:C₁₉H₂₆N₂O₆S
Molecular Weight:410.491
Hs Code.:

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

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

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

There total 7 articles about methyl (2RS,4R)-2-[(1R,4R)-4-benzyloxycarbonylamino-4-carboxy-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: 32.0%

: 216302-09-9
methyl (2RS,4R)-2-[(1R,4S)-4-diphenylmethoxycarbonyl-4-benzyloxycarbonylamino-1-methylbutyl]thiazolidine-4-carboxylate

: 216302-15-7
methyl (2RS,4R)-2-[(1R,4R)-4-benzyloxycarbonylamino-4-carboxy-1-methylbutyl]thiazolidine-4-carboxylate

Guidance literature:: With methoxybenzene; trifluoroacetic acid; at 20 ℃; for 1h;
DOI:10.1248/cpb.47.1532

Reference yield:

: 216301-91-6
diphenylmethyl (2S)-N-benzyloxycarbonyl-6-oxopipecolate

: 216302-15-7
methyl (2RS,4R)-2-[(1R,4R)-4-benzyloxycarbonylamino-4-carboxy-1-methylbutyl]thiazolidine-4-carboxylate

Guidance literature:: Multi-step reaction with 4 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

4.1: 32 percent / TFA; anisole / 1 h / 20 °C

With sodium acetate; acetic acid; methoxybenzene; lithium tri-t-butoxyaluminum hydride; trifluoroacetic acid; 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 / 4.1: Deprotection;
DOI:10.1248/cpb.47.1532

Reference yield:

: 259151-28-5
diphenylmethyl (2S,5S,6RS)-N-benzyloxycarbonyl-6-hydroxy-5-methyl-2-pipecolic acid

: 216302-15-7
methyl (2RS,4R)-2-[(1R,4R)-4-benzyloxycarbonylamino-4-carboxy-1-methylbutyl]thiazolidine-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: AcONa; AcOH / ethanol; methanol; H₂O / 16 h / 20 °C

2: 32 percent / TFA; anisole / 1 h / 20 °C

With sodium acetate; acetic acid; methoxybenzene; trifluoroacetic acid; In methanol; ethanol; water; 1: Condensation / 2: Deprotection;
DOI:10.1248/cpb.47.1532