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

Base Information

• Chemical Name: methyl (phenyl 2,3,4-tri-O-acetyl-α-D-glycopyranosid)uronate
• CAS No.: 37797-57-2
• Molecular Formula: C₁₉H₂₂O₁₀
• Molecular Weight: 410.378
• Mol file: 37797-57-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about methyl (phenyl 2,3,4-tri-O-acetyl-α-D-glycopyranosid)uronate 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: 6.0%

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3) + 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) + methyl (phenyl 2,3,4-tri-O-acetyl-α-D-glycopyranosid)uronate (37797-57-2)

Guidance literature:

With zinc(II) chloride; at 80 ℃; for 2h;

DOI:10.1021/ja209067v

Reference yield:

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2) → methyl (phenyl 2,3,4-tri-O-acetyl-α-D-glycopyranosid)uronate (37797-57-2)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid; acetic acid

2: phenol; zinc chloride; acetic acid / Reagens 4: Acetanhydrid; Erhitzen unter vermindertem Druck

With toluene-4-sulfonic acid; acetic acid; zinc(II) chloride; phenol;

DOI:10.1021/ja01617a047

Reference yield:

methyl 1,2,3,4-tetraacetyl-α-D-glucopyranuronate (5432-32-6) → methyl (phenyl 2,3,4-tri-O-acetyl-α-D-glycopyranosid)uronate (37797-57-2)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen bromide; acetic acid

2: ethanol

3: phenol; zinc chloride; acetic acid / Reagens 4: Acetanhydrid; Erhitzen unter vermindertem Druck

With ethanol; hydrogen bromide; acetic acid; zinc(II) chloride; phenol;

DOI:10.1021/ja01617a047

upstream raw materials:

diazomethane

acetic anhydride

O¹-phenyl-α-D-glucopyranuronic acid

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

Downstream raw materials:

O¹-phenyl-α-D-glucopyranuronic acid methyl ester

methyl (phenyl 2,3-di-O-acetyl-4-deoxy-β-L-threo-hex-4-enopyranosid)uronate

1-O-phenyl-Δ⁴-α-D-glucopyranuronic acid

O¹-phenyl-α-D-glucopyranuronic acid