(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[2-(4-chloro-phenyl)-acetylamino]-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[2-(4-chloro-phenyl)-acetylamino]-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 500339-90-2
• Molecular Formula: C₂₁H₂₄ClNO₁₀
• Molecular Weight: 485.875

Synonyms:(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[2-(4-chloro-phenyl)-acetylamino]-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[2-(4-chloro-phenyl)-acetylamino]-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[2-(4-chloro-phenyl)-acetylamino]-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 2 articles about (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[2-(4-chloro-phenyl)-acetylamino]-tetrahydro-pyran-2-carboxylic 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: 51.0%

2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid methyl ester (67776-38-9,163776-36-1) + 4-chlorophenacetyl chloride (25026-34-0) → (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[2-(4-chloro-phenyl)-acetylamino]-tetrahydro-pyran-2-carboxylic acid methyl ester (500339-90-2)

Guidance literature:

With triphenylphosphine; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1016/j.carres.2004.05.024

Reference yield:

4-chlorophenylacetic Acid (1878-66-6) → (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[2-(4-chloro-phenyl)-acetylamino]-tetrahydro-pyran-2-carboxylic acid methyl ester (500339-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tionyl chloride / toluene / 3 h / 70 °C

2: 51 percent / PPh₃ / acetonitrile / 12 h / 20 °C

With thionyl chloride; triphenylphosphine; In toluene; acetonitrile;

DOI:10.1016/j.carres.2004.05.024

Reference yield: 82.0%

(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[2-(4-chloro-phenyl)-acetylamino]-tetrahydro-pyran-2-carboxylic acid methyl ester (500339-90-2) → 1-{[(4-chlorophenyl)acetyl]amino}-1-deoxy-β-D-glucopyranuronic acid

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 0 ℃;

DOI:10.1016/j.carres.2004.05.024

upstream raw materials:

2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid methyl ester

4-chlorophenacetyl chloride

4-chlorophenylacetic Acid

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