L-Gulonic acid, 2,6-anhydro-, methyl ester, triacetate

Base Information

• Chemical Name: L-Gulonic acid, 2,6-anhydro-, methyl ester, triacetate
• CAS No.: 64723-03-1
• Molecular Formula: C₁₃H₁₈O₉
• Molecular Weight: 318.281
• Mol file: 64723-03-1.mol

Synonyms:L-Gulonic acid, 2,6-anhydro-, methyl ester, triacetate

Chemical Property of L-Gulonic acid, 2,6-anhydro-, methyl ester, triacetate

Chemical Property:

• PSA: 114.43000
• LogP: -0.64670

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Gulonic acid, 2,6-anhydro-, methyl ester, triacetate

There total 2 articles about L-Gulonic acid, 2,6-anhydro-, methyl ester, triacetate 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: 34.2%

methyl tri-O-acetyl-α-L-xylo-hexulopyranosiluronate bromide (25152-12-9) → Methyl-tri-O-acetyl-2,6-anhydro-L-gulonat (64723-03-1) + methyl 3,4,5-tri-O-acetyl-2,6-anhydro-L-idonate (107952-62-5)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; for 0.166667h; Heating;

DOI:10.1016/S0008-6215(00)90357-4

Reference yield:

→ Methyl-tri-O-acetyl-2,6-anhydro-L-gulonat (64723-03-1)

Guidance literature:

DOI:10.1039/c39770000332

Reference yield:

Methyl-tri-O-acetyl-2,6-anhydro-L-gulonat (64723-03-1) → (2S,4S,5S)-4,5-Bis-benzoyloxy-tetrahydro-pyran-2-carboxylic acid allyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / DBU / CH₂Cl₂ / 4 h / Ambient temperature

2: 69 percent / H₂ / Pd/C / methanol / 12 h / Ambient temperature

3: 85 percent / AllONa / 12 h / 0 - 20 °C

4: 61 percent / pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

With pyridine; sodium allyloxide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1055/s-1999-3686

upstream raw materials:

methyl tri-O-acetyl-α-L-xylo-hexulopyranosiluronate bromide

Refernces