2280-43-5

Basic information

• Product Name: 2-O-Hydroxyethyl-D-glucose
• Synonyms: 2-O-Hydroxyethyl-D-glucose
• CAS NO: 2280-43-5
• Molecular Formula: C8H16O7
• Molecular Weight: 224.20844
• Mol File: 2280-43-5.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-O-Hydroxyethyl-D-glucose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-O-Hydroxyethyl-D-glucose(2280-43-5)
• EPA Substance Registry System: 2-O-Hydroxyethyl-D-glucose(2280-43-5)

Safety Data

• Hazardous Substances Data: 2280-43-5(Hazardous Substances Data)

Upstream product

• 78582-37-3 3,5.6-tri-O-benzyl-1,2-O-(1,2-ethanediyl)-α-D-glucofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 55628-55-2 1,2-O-isopropylidene-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 120269-17-2 Benzyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 162843-28-9 benzyl 3,4,6-tri-O-benzyl-2-O-(2-hydroxyethyl)-α-D-glucopyranoside 
• 22329-46-0 1,2-O-(ethane-1,2-diyl)-α-D-glucofuranose 

Relevant articles and documents

FORMATIOM, AND STEREOCHEMISTRY, OF 1,2-O-(1-METHYL-1,2-ETHANEDIYL)-D-GLUCOSE ACETALS FORMED IN THE ACID-CATALYZED HYDROLYSIS OF O-(2-HYDROXYPROPYL)CELLULOSE

In the hydrolysis of O-(2-hydroxypropyl)cellulose, residues of D-glucose substituted with a single O-(2-hydroxypropyl) substituent at O-2 (irrespective of the pattern of additional substitution at O-3 or O-6) form 1,2-O-(1-methyl-1,2-ethanediyl)-α-D-glucose acetals.Based on the characteristics of 2-O-(2-hydroxypropyl)-D-glucose and derivatives thereof in aqueous acid, these bicyclic products are shown to comprise a mixture of two furanose and two pyranose species that differ widely in relative stability, depending on the chirality of C-8 of the 1,4-dioxane ring of the compounds.The order of stability is 1,2-O--α-D-glucopyranose> 1,2-O--α-D-glucofuranose> 1,2-O--α-D-glucopyranose> 1,2-O--α-D-glucofuranose.N.m.r. evidence indicates that the two pyranose derivatives possess the "H-inside" conformation.Acetal formation is less prominent in acidic methanol, although the relative stabilities of the products are similar.Possible mechanisms for these various acid-catalyzed transformations are discussed.

Preparation of O-Hydroxyethyl and O-Hydroxypropyl Derivatives of D-Glucose and 2-Acetamido-2-deoxy-D-glucose for Studies of Modified Hyaluronic Acid

Some hydroxyethyl and hydroxypropyl derivatives of D-glucose and of 2-acetamido-2-deoxy-D-glucose have been sunthesized for use as reference substances for structural studies of hydroxyethylated and hydroxypropylated hyaluronic acid.Hydroxyethyl and hydroxypropyl substituents were introduced in the 2-O- or 3-O-position of D-glucose and in the 4-O- or 6-O-positions of 2-acetamido-2-deoxy-D-glucose by reaction of suitably protected sugars with either ethylene oxide or propylene oxide.For hydroxyethyl derivatives yields varied between 21 and 74percent and with a substantial portion of the doubly alkylated compounds.For hydroxypropyl derivatives yields varied between 15 and 80percent.Only trace amounts of the doubly alkylated compounds were found.The proportions of the respective derivatives were estimated using GLC-MS.All products were characterized by 1H and 13C NMR spectroscopy.