210036-24-1

Basic information

• Product Name: 3-O-[2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL]-D-MANNOPYRANOSE
• Synonyms: N-[(2S,3S,4R,5S)-4,5-Dihydroxy-6-(hydroxymethyl)-2-[(2R,3R,4S,5R)-2,3,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]oxy-tetrahydropyran-3-yl]acetamide
• CAS NO: 210036-24-1
• Molecular Formula: C14H25NO11
• Molecular Weight: 383.35
• Product Categories: Oligosaccharides
• Mol File: 210036-24-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 178-181°C
• Boiling Point: 795.471 °C at 760 mmHg
• Flash Point: 434.886 °C
• Appearance: /
• Density: 1.645 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• Stability: Moisture, temperature and light sensitive
• CAS DataBase Reference: 3-O-[2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL]-D-MANNOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-[2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL]-D-MANNOPYRANOSE(210036-24-1)
• EPA Substance Registry System: 3-O-[2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL]-D-MANNOPYRANOSE(210036-24-1)

Safety Data

• Hazardous Substances Data: 210036-24-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Crystalline Powder

InChI:InChI=1/C14H25NO11/c1-4(18)15-7-10(21)8(19)5(2-16)25-14(7)26-12-9(20)6(3-17)24-13(23)11(12)22/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5?,6?,7-,8+,9+,10+,11+,12-,13+,14-/m0/s1

Upstream product

• 2873-29-2 D-glucal triacetate 
• 223545-65-1 benzyl O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 2280-44-6 D-Glucose 
• 223546-23-4 benzyl O-(2-acetamio-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 83032-25-1 3-O-(2-Acetamido-3,4-di-O-acetyl-2-desoxy-6-O-trityl-α-D-talopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 83032-24-0 3-O-(2-acetoximino-3,4-di-O-acetyl-6-O-trityl-α-D-lyxo-hexopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 83032-23-9 (2R,4R,5R,6R)-2-[(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-4,5-dihydroxy-6-trityloxymethyl-dihydro-pyran-3-one oxime 
• 61865-88-1 3-O-(3,4-didesoxy-6-O-trityl-α-D-glycero-hex-3-enopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 83032-26-2 Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-acetylamino-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 
• 83032-25-1 3-O-(2-Acetamido-2-desoxy-6-O-trityl-α-D-galactopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 78139-15-8 benzyl 3-O-(2-acetamido-3-O-acetyl-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 
• 78139-16-9 benzyl 3-O-(2-acetamido-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 
• 78139-07-8 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl benzylxanthate 

Downstream Products

• 62397-85-7 N-{(2S,3R,4R,5S,6R)-2-[(1R,2S)-1-(1,2-Dihydroxy-ethyl)-2,3,4-trihydroxy-butoxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide 

Relevant articles and documents

Glycosylation using 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucose, - galactose, and -mannose with the aid of p-nitrobenzenesulfonyl chloride- silver trifluoromethanesulfonate-triethylamine system

This report describes a simple synthesis of 2-azido-3,4,6-tri-O-benzyl- 2-deoxy-D-glucopyranose. Glycosylation using this as well as 2-azido-3,4,6- tri-O-benzyl-2-deoxy-D-galactopyranose and -mannopyranose was achieved with the aid of a reagent system consisting of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, and its modifications. O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-(1 → 4)-O-α-D-mannopyranosyl- (1 → 4)-a-D-mannopyranose, the repeating unit of the main chain of the O- specific cell wall polysaccharide of E. coli 058 was synthesized.

SYNTHESE DE DISACCHARIDES A LIAISON α-D PAR CYCLOADDITION: 3-O-α-L-FUCOPYRANOSYL-D-GLUCOSE, 3-O-(2-ACETAMIDO-2-DESOXY-α-D-GALACTOPYRANOSYL)-D-GLUCOSE ET 3-O-α-D-TALOPYRANOSYL-D-GLUCOSE

Reduction of the primary alcohol group of 1,2:5,6-isopropylidene-3-O-(2,3,4-trideoxy-α-L-glycero-hex-2-enopyranosyl)-α-D-glucofuranose by p-toluenesulfonylation, substitution by iodine, and tributylstannane treatment, gave a 6'-deoxy derivative, which was