(2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-5-({(Z)-(methylsulfanyl)[(methylsulfonyl)imino]methyl}amino)pentanoic acid

Base Information

• Chemical Name: (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-5-({(Z)-(methylsulfanyl)[(methylsulfonyl)imino]methyl}amino)pentanoic acid
• CAS No.: 383173-92-0
• Molecular Formula: C₁₇H₂₅N₃O₆S₂
• Molecular Weight: 431.534

Synonyms:(2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-5-({(Z)-(methylsulfanyl)[(methylsulfonyl)imino]methyl}amino)pentanoic acid

Chemical Property of (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-5-({(Z)-(methylsulfanyl)[(methylsulfonyl)imino]methyl}amino)pentanoic acid

Chemical Property:

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Technology Process of (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-5-({(Z)-(methylsulfanyl)[(methylsulfonyl)imino]methyl}amino)pentanoic acid

There total 10 articles about (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-5-({(Z)-(methylsulfanyl)[(methylsulfonyl)imino]methyl}amino)pentanoic 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:

(2S,3R)-2-Benzyloxycarbonylamino-5-({[(Z)-methanesulfonylimino]-methylsulfanyl-methyl}-amino)-3-methyl-pentanoic acid tert-butyl ester → (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-5-({(Z)-(methylsulfanyl)[(methylsulfonyl)imino]methyl}amino)pentanoic acid (383173-92-0)

Guidance literature:

With chlorotriisopropylsilane; methyl-phenyl-thioether; trifluoroacetic acid; In water; at 20 ℃; for 1h;

DOI:10.1021/jm0102654

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-5-({(Z)-(methylsulfanyl)[(methylsulfonyl)imino]methyl}amino)pentanoic acid (383173-92-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 2N aq. NaOH / 5.75 h / 0 - 23 °C

2.1: toluene / 1.75 h / 80 °C

3.1: thexylborane / tetrahydrofuran / 1 h / 0 - 20 °C

3.2: 30percent aq. H₂O₂ / aq. phosphate buffer / 14 h / 20 °C / pH 7.0

4.1: pyridine / CH₂Cl₂ / 14 h

5.1: LiN₃ / dimethylformamide / 3 h / 50 °C

6.1: H₂; TEA / Lindlar catalyst / methanol / 4 h / 1551.49 Torr

7.1: aq. NaOAc / ethanol / 48 h / Heating

8.1: CF₃COOH; thioanizole; iPr₃SiH / H₂O / 1 h / 20 °C

With pyridine; sodium hydroxide; lithium azide; chlorotriisopropylsilane; methyl-phenyl-thioether; thexylborane; TEA; hydrogen; sodium acetate; trifluoroacetic acid; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm0102654

Reference yield:

(2S,3R)-(+)-2-Amino-3-methylpent-4-enoic acid (249553-80-8) → (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-5-({(Z)-(methylsulfanyl)[(methylsulfonyl)imino]methyl}amino)pentanoic acid (383173-92-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 2N aq. NaOH / 5.75 h / 0 - 23 °C

2.1: toluene / 1.75 h / 80 °C

3.1: thexylborane / tetrahydrofuran / 1 h / 0 - 20 °C

3.2: 30percent aq. H₂O₂ / aq. phosphate buffer / 14 h / 20 °C / pH 7.0

4.1: pyridine / CH₂Cl₂ / 14 h

5.1: LiN₃ / dimethylformamide / 3 h / 50 °C

6.1: H₂; TEA / Lindlar catalyst / methanol / 4 h / 1551.49 Torr

7.1: aq. NaOAc / ethanol / 48 h / Heating

8.1: CF₃COOH; thioanizole; iPr₃SiH / H₂O / 1 h / 20 °C

With pyridine; sodium hydroxide; lithium azide; chlorotriisopropylsilane; methyl-phenyl-thioether; thexylborane; TEA; hydrogen; sodium acetate; trifluoroacetic acid; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm0102654

upstream raw materials:

benzyl chloroformate

(2S,3R)-(+)-2-Amino-3-methylpent-4-enoic acid

(2S,3R)-2-benzyloxycarbonylamino-3-methyl-4-pentenoic acid

tert-butyl (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-4-pentenoate

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