methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(methylsufonyloxy)pentanoate

Base Information

• Chemical Name: methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(methylsufonyloxy)pentanoate
• CAS No.: 174488-13-2
• Molecular Formula: C₁₅H₂₁NO₇S
• Molecular Weight: 359.4

Synonyms:methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(methylsufonyloxy)pentanoate

Chemical Property of methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(methylsufonyloxy)pentanoate

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Technology Process of methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(methylsufonyloxy)pentanoate

There total 3 articles about methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(methylsufonyloxy)pentanoate 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: 96.0%

methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(hydroxy)pentanoate (141406-83-9) + methanesulfonyl chloride (124-63-0) → methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(methylsufonyloxy)pentanoate (174488-13-2)

Guidance literature:

With triethylamine; In dichloromethane; for 0.583333h;

DOI:10.1021/jm991119p

Reference yield:

Z-L-GluOMe (5672-83-3) → methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(methylsufonyloxy)pentanoate (174488-13-2)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / tetrahydrofuran / 0.17 h / -10 °C

2: NaBH₄ / methanol; tetrahydrofuran / 0.67 h / 0 °C

3: 96 percent / Et₃N / CH₂Cl₂ / 0.58 h

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm991119p

Reference yield:

(S)-2-Benzyloxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid methyl ester (117836-15-4) → methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(methylsufonyloxy)pentanoate (174488-13-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol; tetrahydrofuran / 0.67 h / 0 °C

2: 96 percent / Et₃N / CH₂Cl₂ / 0.58 h

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm991119p

upstream raw materials:

methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(hydroxy)pentanoate

methanesulfonyl chloride

Z-L-GluOMe

(S)-2-Benzyloxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid methyl ester

Downstream raw materials:

methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(1H-1,2,4-triazol-3-ylthio)-pentanoate

methyl (2S)-2-{4-[N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]benzamido}-5-(1H-1,2,4-triazol-3-ylsulfonyl)pentanoate

methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(1H-1,2,4-triazol-3-ylsulfonyl)pentanoate

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