(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-chloro-2-formyl-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-chloro-2-formyl-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 148580-09-0
• Molecular Formula: C₂₀H₂₁ClO₁₁
• Molecular Weight: 472.833

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

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

Chemical Property:

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

There total 1 articles about (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-chloro-2-formyl-phenoxy)-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: 86.0%

5-chlorosalicyclaldehyde (635-93-8) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-chloro-2-formyl-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (148580-09-0)

Guidance literature:

With 2,4,6-trimethyl-pyridine; silver carbonate; In dichloromethane; for 96h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00413-4

Reference yield: 94.0%

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-chloro-2-formyl-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (148580-09-0) → 4-chloro-2-formylphenyl β-D-glucuronic acid methyl ester (192203-17-1)

Guidance literature:

With sodium methylate; In methanol; 1.) 0 deg C, 2 h, 2.) room temperature, 4 h;

DOI:10.1016/S0040-4020(97)00413-4

Reference yield: 90.0%

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-chloro-2-formyl-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (148580-09-0) → (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-chloro-2-hydroxymethyl-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (148580-10-3)

Guidance literature:

With sodium tetrahydroborate; silica gel; In chloroform; isopropyl alcohol; at 0 ℃; for 0.75h;

DOI:10.1021/jm970589l

upstream raw materials:

5-chlorosalicyclaldehyde

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

Downstream raw materials:

4-chloro-2-formylphenyl β-D-glucuronic acid methyl ester

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-chloro-2-hydroxymethyl-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

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

C₄₂H₄₄ClNO₂₀

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