Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate)

Base Information

• Chemical Name: Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate)
• CAS No.: 107952-66-9
• Molecular Formula: C₁₄H₂₀O₁₀
• Molecular Weight: 348.307
• Mol file: 107952-66-9.mol

Synonyms:Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate)

Chemical Property of Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate)

Chemical Property:

• PSA: 115.82000
• LogP: -0.51680
• Storage Temp.: Refrigerator
• Solubility.: Acetone, Chloroform, Dichloromethane, Ethanol, Ethyl Acetate, Methanol

Purity/Quality:

95% ^*data from raw suppliers

Methyl3,4-Di-O-acetyl-β-L-idopyranosiduronate1,2-(Methylorthoacetate) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 3,4-Di-O-acetyl-β-L-idopyranosiduronate 1,2-(Methylorthoacetate) (cas# 107952-66-9 ) is a compound useful in organic synthesis.

Technology Process of Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate)

There total 5 articles about Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate) 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: 77.4%

methanol (67-56-1) + methyl (2,3,4-tetra-O-acetyl-α-L-idopyranosyl bromide)uroate (108032-44-6) → methyl 3,4-di-O-acetyl-β-L-idopyranouronate 1,2-(methyl orthoacetate) (107952-66-9)

Guidance literature:

With 2,4,6-trimethyl-pyridine; In dichloromethane; for 24h; Ambient temperature;

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

Reference yield:

methyl 1,2,3,4-tetra-O-acetyl-α-L-idopyranuronate (108032-41-3) → methyl 3,4-di-O-acetyl-β-L-idopyranouronate 1,2-(methyl orthoacetate) (107952-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / 30percent HBr in AcOH / 4 h / Ambient temperature

2: 77.4 percent / 2,4,6-trimethylpyridine / CH₂Cl₂ / 24 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; hydrogen bromide; In dichloromethane;

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

Reference yield:

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) → methyl 3,4-di-O-acetyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranuronate (107952-66-9,136598-87-3,136598-88-4)

Guidance literature:

Multi-step reaction with 2 steps

1: iodine / 1,2-dichloro-ethane / 0.5 h / Reflux

2: tetrabutylammomium bromide / methanol / 2 h / Reflux

With tetrabutylammomium bromide; iodine; In methanol; 1,2-dichloro-ethane;

DOI:10.1002/ejoc.201201084

upstream raw materials:

methanol

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate

methyl (2,3,4-tri-O-acetyl-α-D-glucopyranosyl iodide)uronate

methyl (2,3,4-tetra-O-acetyl-α-L-idopyranosyl bromide)uroate