1-O--β-D-glucopyranuronic acid

Base Information

• Chemical Name: 1-O--β-D-glucopyranuronic acid
• CAS No.: 78008-86-3
• Molecular Formula: C₂₀H₂₇NO₁₀
• Molecular Weight: 441.435
• Mol file: 78008-86-3.mol

Synonyms:1-O--β-D-glucopyranuronic acid

Chemical Property of 1-O--β-D-glucopyranuronic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O--β-D-glucopyranuronic acid

There total 6 articles about 1-O--β-D-glucopyranuronic acid 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: 73.0%

benzyl 2,3,4-tri-O-benzyl-1-O--D-glucopyranuronate (78008-84-1) → 1-O--β-D-glucopyranuronic acid (78008-86-3)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; In 2-methoxy-ethanol; for 24h;

DOI:10.1016/S0008-6215(00)84580-2

Reference yield: 63.0%

(2S,3S,4S,5R,6S)-6-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid allyl ester → 1-O--β-D-glucopyranuronic acid (78008-86-3)

Guidance literature:

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4039(97)00135-4

Reference yield:

2,3,4-tri-O-benzyl-D-glucopyranosideuronic acid benzyl ester (4539-78-0) → 1-O--β-D-glucopyranuronic acid (78008-86-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 300 mg / imidazole / CH₂Cl₂ / 24 h / Ambient temperature

2: 73 percent / H₂, acetic acid / palladium-on-charcoal, 10percent / 2-methoxy-ethanol / 24 h

With 1H-imidazole; hydrogen; acetic acid; palladium on activated charcoal; In dichloromethane; 2-methoxy-ethanol;

DOI:10.1016/S0008-6215(00)84580-2

upstream raw materials:

benzyl 2,3,4-tri-O-benzyl-1-O--D-glucopyranuronate

N-tert-butoxycarbonyl-L-phenylalanine

allyl (2S,3S,4S,5R)-3,4,5,6-tetrahydroxytetrahydropyran-2-carboxylate

2,3,4-tri-O-benzyl-D-glucopyranosideuronic acid benzyl ester

Downstream raw materials:

methyl 2,3,4-tri-O-acetyl-1-O-(N-acetyl-L-phenylalanyl)-β-D-glucopyranuronate