(2S,3S)-2-Benzyloxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester

Base Information

• Chemical Name: (2S,3S)-2-Benzyloxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester
• CAS No.: 858669-59-7
• Molecular Formula: C₂₁H₂₅NO₅S
• Molecular Weight: 403.499
• Mol file: 858669-59-7.mol

Synonyms:(2S,3S)-2-Benzyloxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester

Chemical Property of (2S,3S)-2-Benzyloxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-Benzyloxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester

There total 5 articles about (2S,3S)-2-Benzyloxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester 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: 87.0%

(2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid methyl ester (85550-10-3) + p-methoxybenzylmercaptan (6258-60-2) → (2S,3S)-2-Benzyloxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester (858669-59-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 10h;

DOI:10.1021/ol0507930

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S,3S)-2-Benzyloxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester (858669-59-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaHCO₃ / ethyl acetate

2: 87 percent / BF₃*OEt₂ / CH₂Cl₂ / 10 h / 0 °C

With boron trifluoride diethyl etherate; sodium hydrogencarbonate; In dichloromethane; ethyl acetate;

DOI:10.1021/ol0507930

Reference yield:

N-trityl-D-threonine methyl ester (85482-79-7) → (2S,3S)-2-Benzyloxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester (858669-59-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / MsCl; Et₃N / tetrahydrofuran / Heating

2: TFA / CH₂Cl₂; methanol

3: NaHCO₃ / ethyl acetate

4: 87 percent / BF₃*OEt₂ / CH₂Cl₂ / 10 h / 0 °C

With boron trifluoride diethyl etherate; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ol0507930

upstream raw materials:

(2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid methyl ester

p-methoxybenzylmercaptan

benzyl chloroformate

(2R,3R)-3-MeAzyOMe

Downstream raw materials:

methyl (2Z)-2-(N-benzyloxycarbonylamino)but-2-enoate

(2S,3S)-N-benzyloxycarbonyl-3-methylcysteine methyl ester