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

Base Information

• Chemical Name: 2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester
• CAS No.: 4630-61-9
• Molecular Formula: C₁₉H₂₂O₁₀
• Molecular Weight: 410.378
• Mol file: 4630-61-9.mol

Synonyms:2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester

Chemical Property of 2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester

There total 19 articles about 2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic 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: 92.0%

phenyltrimethylsilyl ether (1529-17-5) + (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2) → 2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester (4630-61-9)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1002/anie.200353196

Reference yield: 72.0%

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) + phenol (108-95-2,27073-41-2) → 2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester (4630-61-9)

Guidance literature:

With pyrylium tetrafluoroborate; In toluene; at 60 ℃; for 1h; diastereoselective reaction; Sealed tube;

DOI:10.1002/anie.202115394

Reference yield: 66.0%

phenol (108-95-2,27073-41-2) + (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2) → 2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester (4630-61-9)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1002/anie.200353196

upstream raw materials:

acetic anhydride

methyl phenyl-β-D-glucuronate

potassium phenolate

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

Downstream raw materials:

methyl (phenyl 2,3,4-tri-O-acetyl-α-D-glycopyranosid)uronate

phenyl β-D-glucuronide

methyl phenyl-β-D-glucuronate

O²,O³,O⁴-triacetyl-O¹-phenyl-β-D-glucopyranuronic acid amide