(S)-2-Benzyloxycarbonylamino-3-fluorocarbonyl-propionic acid isobutyl ester

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-3-fluorocarbonyl-propionic acid isobutyl ester
• CAS No.: 408363-46-2
• Molecular Formula: C₁₆H₂₀FNO₅
• Molecular Weight: 325.337

Synonyms:(S)-2-Benzyloxycarbonylamino-3-fluorocarbonyl-propionic acid isobutyl ester

Chemical Property of (S)-2-Benzyloxycarbonylamino-3-fluorocarbonyl-propionic acid isobutyl ester

Chemical Property:

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Technology Process of (S)-2-Benzyloxycarbonylamino-3-fluorocarbonyl-propionic acid isobutyl ester

There total 2 articles about (S)-2-Benzyloxycarbonylamino-3-fluorocarbonyl-propionic acid isobutyl 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: 92.0%

(S)-2-Benzyloxycarbonylamino-succinic acid 1-isobutyl ester (69875-23-6) → (S)-2-Benzyloxycarbonylamino-3-fluorocarbonyl-propionic acid isobutyl ester (408363-46-2)

Guidance literature:

With pyridine; trifluoro-[1,3,5]triazine; In dichloromethane;

DOI:10.1055/s-2002-19355

Reference yield:

(4S)-3-benzyloxycarbonyl-4-carboxymethyl-1,3-oxazolidin-5-one (23632-66-8) → (S)-2-Benzyloxycarbonylamino-3-fluorocarbonyl-propionic acid isobutyl ester (408363-46-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 47 percent / i-BuONa / 3 h / 65 °C

2: 92 percent / cyanuric fluoride; pyridine / CH₂Cl₂

With pyridine; trifluoro-[1,3,5]triazine; sodium isobutoxide; In dichloromethane;

DOI:10.1055/s-2002-19355

Reference yield: 84.0%

2-acetamido-2-deoxy-β-D-glucopyranosylamine (4229-38-3,102039-79-2,115350-20-4,133677-75-5,137493-97-1) + (S)-2-Benzyloxycarbonylamino-3-fluorocarbonyl-propionic acid isobutyl ester (408363-46-2) → (S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-benzyloxycarbonylamino-succinamic acid isobutyl ester (408363-43-9)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1055/s-2002-19355

upstream raw materials:

(S)-2-Benzyloxycarbonylamino-succinic acid 1-isobutyl ester

(4S)-3-benzyloxycarbonyl-4-carboxymethyl-1,3-oxazolidin-5-one

Downstream raw materials:

(S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-benzyloxycarbonylamino-succinamic acid isobutyl ester

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