(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,5-dimethyl-benzoylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,5-dimethyl-benzoylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 500340-02-3
• Molecular Formula: C₂₂H₂₇NO₁₀
• Molecular Weight: 465.457

Synonyms:(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,5-dimethyl-benzoylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,5-dimethyl-benzoylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,5-dimethyl-benzoylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 2 articles about (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,5-dimethyl-benzoylamino)-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: 56.0%

3,5-dimethylbenzoic acid (499-06-9) + 2,3,4-tri-O-acetyl-β-D-glucopyranosylamine uronic acid methyl ester (14365-73-2) → (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,5-dimethyl-benzoylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester (500340-02-3)

Guidance literature:

With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/j.carres.2004.05.024

Reference yield:

2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid methyl ester (67776-38-9,163776-36-1) → (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,5-dimethyl-benzoylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester (500340-02-3)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / tetrahydrofuran / -5 °C

2: 56 percent / HOBT; DMAP; DCC / tetrahydrofuran / 12 h / 20 °C

With dmap; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/j.carres.2004.05.024

Reference yield: 85.0%

(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,5-dimethyl-benzoylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester (500340-02-3) → 1-deoxy-1-[(3,5-dimethylbenzoyl)amino]-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:

3,5-dimethylbenzoic acid

2,3,4-tri-O-acetyl-β-D-glucopyranosylamine uronic acid methyl ester

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

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