4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate

Base Information

• Chemical Name: 4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate
• CAS No.: 92420-85-4
• Molecular Formula: C₂₀H₂₄O₁₀
• Molecular Weight: 424.405

Synonyms:4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate

Chemical Property of 4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate

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Technology Process of 4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate

There total 6 articles about 4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate 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: 80.0%

p-cresol (106-44-5) + methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) → 4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate (92420-85-4)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 1h;

Reference yield: 69.0%

p-cresol (106-44-5) + (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2) → 4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate (92420-85-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 3h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2020.108225

Reference yield: 55.0%

p-cresol (106-44-5) + methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9) → 4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate (92420-85-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 0 ℃; for 1h;

DOI:10.1021/jo00199a046

upstream raw materials:

p-cresol

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

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

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate

Downstream raw materials:

O¹-p-tolyl-β-D-glucopyranuronic acid methyl ester

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

4-Methylphenol glucuronide

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-(2,5-dioxo-pyrrolidin-1-yloxycarbonyloxymethyl)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

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