127676-61-3

Basic information

• Product Name: 2,5-ANHYDRO-D-MANNOSE OXIME
• Synonyms: 2,5-Anhydro-D-mannofuranoseoxime
• CAS NO: 127676-61-3
• Molecular Formula: C6H11NO5
• Molecular Weight: 177.155
• Product Categories: Carbohydrates & Derivatives;Inhibitors
• Mol File: 127676-61-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,5-ANHYDRO-D-MANNOSE OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-ANHYDRO-D-MANNOSE OXIME(127676-61-3)
• EPA Substance Registry System: 2,5-ANHYDRO-D-MANNOSE OXIME(127676-61-3)

Safety Data

• Hazardous Substances Data: 127676-61-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Anhydro-D-Mannose Oxime is used as a key intermediate compound for the synthesis of C-(D-glycopyranosyl)ethylamines and C-(D-glycofuranosyl)methylamines. These synthesized compounds have potential applications as glycosidase inhibitors, which are important in the development of drugs targeting various diseases, including those related to carbohydrate metabolism and infections caused by glycosidase-producing pathogens.

Upstream product

• 495-75-0 2,5-anhydro-D-mannose 
• 14131-63-6 D-glucosamine hydrochloride 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 

Downstream Products

• 38642-50-1 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl cyanide 
• 228862-97-3 1-C-(α-D-arabinofuranosyl)methylamine 
• 127676-62-4 C₃₀H₂₇NO₇ 

Relevant articles and documents

Flow synthesis of a versatile fructosamine mimic and quenching studies of a fructose transport probe

We describe the synthesis of 1-amino-2,5-anhydro-D-mannose ("mannitolamine"), a key intermediate to the 7-nitro-1,2,3- benzadiazole conjugate (NBDM), using commercially available fluidic devices to increase the throughput. The approach is the first example of a flow-based Tiffeneau-Demjanov rearrangement. Performing this step in flow enables a ～64-fold throughput enhancement relative to batch. The flow process enables the synthesis to be accomplished three times faster than the comparable batch route. The high throughput enabled the production of larger quantities of the fluorescent fructose transport probe NBDM, enabling us to measure key photophysical properties that will facilitate future uptake studies.

An easy stereospecific synthesis of 1-amino-2,5-anhydro-1-deoxy-D-mannitol and arylamino derivatives

1-Amino-2,5-anhydro-1-deoxy-D-mannitol and a series of arylamino derivatives were prepared by nitrous acid deamination of 2-amino-2-deoxy-D-glucose and subsequent reductive amination of the resulting 2,5-anhydro-D-mannose. Some of these compounds showed a

Synthesis of C-(D-glycopyranosyl)ethylamines and C-(D-glycofuranosyl)methylamines as potential glycosidase inhibitors

The C-glucosyl aldehyde, 2-C-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)ethanal was prepared from the C-glucopyranosyl propene precursor by ozonolysis. Reductive amination of the C-glucosyl aldehyde and subsequent deprotection gave 1-anilino-2-C-(α-D-glucopyranosyl)ethane. The E and Z isomers of the oxime derivative, 1-C-(α-D-arabinofuranosyl)methanal oxime were prepared by treating their aldehyde precursor with hydroxylamine. Acetylation of the oxime, followed by catalytic hydrogenation and deprotection, gave the corresponding 1-C-(α-D-arabinofuranosyl)methylamine. Reductive amination of ethyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside using aniline gave ethyl 5-anilino-5-deoxy-D-lyxo-furanoside. Inhibition studies with these compounds on β-D-glucosidase from sweet almond, using o-nitrophenyl D-glucopyranoside as substrate, were carried out. Copyright (C) 1999 Elsevier Science Ltd.

Preparation of Modified Nucleosides from Glucosamine: Rapid and Efficient Formal Total Synthesis of Several 2'-Deoxy C-Nucleosides

Formal total syntheses of several 2'-deoxy C-nucleosides have been accomplished in a short and efficient process using D-glucosamine as the starting material.