71021-05-1

Basic information

• Product Name: .beta.-D-erythro-Hexopyranos-2-ulose, 1,6-anhydro-3-deoxy-4-O-methyl-
• Synonyms: .beta.-D-erythro-Hexopyranos-2-ulose, 1,6-anhydro-3-deoxy-4-O-methyl-
• CAS NO: 71021-05-1
• Molecular Formula: C7H10O4
• Molecular Weight: 158.1519
• Mol File: 71021-05-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: .beta.-D-erythro-Hexopyranos-2-ulose, 1,6-anhydro-3-deoxy-4-O-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: .beta.-D-erythro-Hexopyranos-2-ulose, 1,6-anhydro-3-deoxy-4-O-methyl-(71021-05-1)
• EPA Substance Registry System: .beta.-D-erythro-Hexopyranos-2-ulose, 1,6-anhydro-3-deoxy-4-O-methyl-(71021-05-1)

Safety Data

• Hazardous Substances Data: 71021-05-1(Hazardous Substances Data)

Usage

Description

.beta.-D-erythro-Hexopyranos-2-ulose, 1,6-anhydro-3-deoxy-4-O-methyl-, also known as 4-O-methyl-d-fructose, is a rare carbohydrate compound with the molecular formula C7H12O5. It is a derivative of hexopyranose and has been studied for its potential applications in various industries due to its unique properties.

Uses

Used in the Food Industry:
.beta.-D-erythro-Hexopyranos-2-ulose, 1,6-anhydro-3-deoxy-4-O-methylis used as a low-calorie sweetener for its potential application in the food industry. Its unique properties make it a promising candidate for developing healthier and more sustainable sweetening options.
Used in Medicinal Applications:
In the pharmaceutical industry, .beta.-D-erythro-Hexopyranos-2-ulose, 1,6-anhydro-3-deoxy-4-O-methylis investigated for its potential medicinal properties, particularly its impact on glucose metabolism. .beta.-D-erythro-Hexopyranos-2-ulose, 1,6-anhydro-3-deoxy-4-O-methylmay contribute to the development of new drugs for managing diabetes and other metabolic disorders.
Used in the Synthesis of Complex Carbohydrate Molecules:
.beta.-D-erythro-Hexopyranos-2-ulose, 1,6-anhydro-3-deoxy-4-O-methylis also studied for its potential as a building block in the synthesis of other complex carbohydrate molecules. This application can be beneficial in various industries, including pharmaceuticals, cosmetics, and materials science, where complex carbohydrates play a crucial role in the development of new products and technologies.

Upstream product

• 37112-31-5 levoglucosenone 
• 67-56-1 methanol 
• 75-52-5 nitromethane 

Relevant articles and documents

The conversion of levoglucosenone into isolevoglucosenone

Levoglucosenone (1), a compound that will soon be available in tonne quantities through the pyrolysis of acid-treated lignocellulosic biomass, has been converted into isolevoglucosenone (2) using Wharton rearrangement chemistry. Treatment of compound 1 with alkaline hydrogen peroxide gave the γ-lactones 5 and 6 rather than the required epoxy-ketones 3 and/or 4. However, the latter pair of compounds could be obtained by an initial Luche reduction of compound 1, electrophilic epoxidation of the resulting allylic alcohol 8 and oxidation of the product oxiranes 9 and 10. Independent treatment of compounds 3 and 4 with hydrazine then acetic acid followed by oxidation of the ensuing allylic alcohols finally afforded isolevoglucosenone (2). Details of the single-crystal X-ray analyses of epoxy-alcohols 9 and 10 are reported.

Stereoselective Addition of Nitromethane to Levoglucosenone; Formation and Structure of 2:1 and 1:2 Adducts

Tetramethylguanidine-catalysed addition of nitromethane to levoglucosenone affords in 98percent yield a 10:1 mixture of 2:1 adducts 2 and 3, which result from initial Michael addition of nitromethanide excusively from the exo face at C-4, followed by further reaction of the nitronate anion at both faces of the 1:1 adduct 4.In the presence of excess of levoglucosenone the major product (95percent) is a pentacyclic 1:2 adduct 6, formed by reaction of 1:1 adduct 4 with further levoglucosenone.MeOH-levoglucosenone-MeNO2 adduct 12 and 2:2 adduct 7 were also formed as by-products in the corresponding diethylamine-catalysed reaction in methanol.The structure of compound 6 was established by X-ray crystallography.