68499-61-6

Basic information

• Product Name: 1,3,4,6-tetra-O-acetyl-2-[(bromoacetyl)amino]-2-deoxy-beta-D-glucopyranose
• CAS NO: 68499-61-6
• Molecular Formula: C₁₆H₂₂BrNO₁₀
• Molecular Weight: 468.2506
• Mol File: 68499-61-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 563.3°C at 760 mmHg
• Flash Point: 294.5°C
• Density: 1.49g/cm³
• Vapor Pressure: 1.03E-12mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: 1,3,4,6-tetra-O-acetyl-2-[(bromoacetyl)amino]-2-deoxy-beta-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6-tetra-O-acetyl-2-[(bromoacetyl)amino]-2-deoxy-beta-D-glucopyranose(68499-61-6)
• EPA Substance Registry System: 1,3,4,6-tetra-O-acetyl-2-[(bromoacetyl)amino]-2-deoxy-beta-D-glucopyranose(68499-61-6)

Safety Data

• Hazardous Substances Data: 68499-61-6(Hazardous Substances Data)

Usage

General Description

1,3,4,6-tetra-O-acetyl-2-[(bromoacetyl)amino]-2-deoxy-beta-D-glucopyranose is a synthetic chemical compound that is derived from glucose. It is an acetylated derivative of 2-deoxyglucose, a glucose analogue that has been studied for its potential therapeutic applications in cancer treatment. The addition of bromoacetylamine to the glucose molecule introduces a reactive bromine group, which may allow for further modification of the compound for specific research or pharmaceutical purposes. The acetyl groups on the glucose molecule serve to protect the hydroxyl groups, making the compound more stable and less reactive. 1,3,4,6-tetra-O-acetyl-2-[(bromoacetyl)amino]-2-deoxy-beta-D-glucopyranose may be of interest for further research into its potential biological activities and therapeutic applications.

Upstream product

• 22118-09-8 2-bromoacetyl chloride 
• 17460-45-6 tetra-acetyl glucosamine 

Relevant articles and documents

Haloacetamido analogues of 2-amino-2-deoxy-d-glucose and 2-amino-2-deoxy-d-galactose. Syntheses and effects on the Friend murine erythroleukemia

2-Deoxy-2(haloacetamido)-D-glucose and 2-deoxy-2-(haloacetamido)-D-galactose (fluoro, chloro, and bromo) were prepared by de-O-acetylation of the appropriate 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(haloacetamido)-β-D-hexose with triethylamine. The 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(chloroacetamido)- and 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(bromoacetamido)-β-D-hexoses were produced by condensation of a haloacetyl anhydride with 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β-D-hexose hydrochloride in pyridine. The hydrochlorides were converted to free bases for condensation with fluoroacetic acid in the presence of dicyclohexylcarbodiimide to produce 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(fluoroacetamido)-β-D-hexoses. The chloroacetamido and bromoacetamido derivatives were from 3- to 12-fold more toxic on a molar basis to BDF1 mice when administerd as lipophilic tetra-O-acetates than as the free sugars; no significant difference existed between the glucose and galactose forms. The fluoroacetamido analogue of the glucose series was fivefold more toxic than the comparable fluoroacetamido derivative of the galactose series; no difference existed in the toxicities of the free sugars and the tetra-O-acetates with either of the fluoseries; no difference existed in the toxicities of the free sugars and the tetra-O-acetates with either of the fluoroacetamide-containing hexoses. Cytotoxicity against log-phase cultured Friend erythroleukemia cells was greatest with the tetra-O-acetylated bromoacetamido derivatives in both the gluco and galacto series, these agents being three- to fourfold more cytotoxic than tetra-O-acetylated chloroacetamido derivatives and 20-fold more cytotoxic than tetra-O-acetylated fluoroacetamido sugars. The N-chloroacetamido derivative in the glucose series was 50-fold more cytotoxic as the tetra-O-acetate than as the free nonacetylated sugar. These results support the concept that tetra-O-acetylated derivatives of the chloroacetamido and bromoacetamido carbohydrate analogues function as lipophilic alkylating agents and lose biological activity when converted to hydrophilic free hydroxyl forms, whereas the fluoroacetamido derivatives exert their effects as the de-O-acetylated form.