107952-66-9

Basic information

• Product Name: Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate)
• Synonyms: Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate)
• CAS NO: 107952-66-9
• Molecular Formula: C14H20O10
• Molecular Weight: 348.3026
• Product Categories: Carbohydrates & Derivatives
• Mol File: 107952-66-9.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Acetone, Chloroform, Dichloromethane, Ethanol, Ethyl Acetate, Methanol
• CAS DataBase Reference: Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate)(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate)(107952-66-9)
• EPA Substance Registry System: Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate)(107952-66-9)

Safety Data

• Hazardous Substances Data: 107952-66-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate) is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows it to be a valuable building block in the synthesis of complex molecules, particularly in the pharmaceutical and chemical industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate) is used as a key component in the development of new drugs. Its versatile chemical properties enable it to be modified and incorporated into a wide range of therapeutic agents, potentially leading to the discovery of novel medications with improved efficacy and reduced side effects.
Used in Chemical Industry:
Methyl 3,4-Di-O-acetyl--L-idopyranosiduronate, 1,2-(Methylorthoacetate) is also utilized in the chemical industry for the production of various specialty chemicals, such as additives, coatings, and polymers. Its unique structure and properties make it a valuable asset in the development of innovative materials with enhanced performance characteristics.

Upstream product

• 108032-41-3 methyl 1,2,3,4-tetra-O-acetyl-α-L-idopyranuronate 
• 67-56-1 methanol 
• 108032-44-6 methyl (2,3,4-tetra-O-acetyl-α-L-idopyranosyl bromide)uroate 
• 108800-87-9 methyl (2,3,4-tri-O-acetyl-α-D-glucopyranosyl iodide)uronate 
• 3082-96-0 methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate 

Relevant articles and documents

Polymethylhydrosiloxane (PMHS): A convenient option for synthetic applications of the iodine/silane combined reagent - Straightforward entries to 2-hydroxyglycals and useful building-blocks of glucuronic acid and glucosamine

Polymethylhydrosiloxane (PMHS) proved to be a practically convenient alternative to triethylsilane in a large set of synthetic elaborations entailing the quick generation of glycosyl iodides with a iodine/silane combined reagent. In addition, the scope of this combined reagent was expanded to the especially fast generation of 2-acetoxyglycals, and the rapid synthesis of useful building-blocks of D-glucuronic acids and D-glucosamine. All the synthetic targets were obtained in especially short times either via one-pot procedures or through experimental sequences devoid of laborious chromatographical purifications of intermediates. Polymethylhydrosiloxane (PMHS) is a practically convenient alternative to triethylsilane in a large set of synthetic elaborations entailing the quick generation of glycosyl iodides with a iodine/silane combined reagent. Copyright

APPLICATION OF A RADICAL REACTION TO THE SYNTHESIS OF L-IDURONIC ACID DERIVATIVES FROM D-GLUCURONIC ACID ANALOGUES

Commercially available D-glucofuranuro-6,3-lactone was transformed into the known, crystalline methyl (5R)-1,2,3,4-tetra-O-acetyl-5-C-bromo-β-D-glucopyranuronate (3) in three steps.Reduction with tributyltin hydride gave crystalline methyl 1,2,3,4-tetra-O-acetyl-α-L-idopyranuronate (4) in ca. 30percent yield, together with the crystalline methyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate (1, 63.5percent) which may be separated and converted back by Ferrier's photobromination into 3.This procedure provides the first practical and expenditious conversion of D-glucuronic into L-iduronic acid by epimerization.Acetate 4 was converted in quantitative yield into methyl (2,3,4-tri-O-acetyl-α-L-idopyranosyl bromide)-uronate (22), and then into methyl 3,4-di-O-acetyl-β-L-idopyranuronate 1,2-(methyl orthoester) (23), which are useful compouns for glycosylation reactions.Various β-D-glucuronic acid derivatives have been epimerized to α-L-iduronic acid analogues by this novel procedure.