10385-49-6

Basic information

• Product Name: 1,3,4,6-tetra-O-acetyl-2-(benzoylamino)-2-deoxyhexopyranose
• CAS NO: 10385-49-6
• Molecular Formula: C₂₁H₂₅NO₁₀
• Molecular Weight: 451.4239
• Mol File: 10385-49-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 600°C at 760 mmHg
• Flash Point: 316.6°C
• Density: 1.32g/cm³
• Vapor Pressure: 2.36E-14mmHg at 25°C
• Refractive Index: 1.538
• CAS DataBase Reference: 1,3,4,6-tetra-O-acetyl-2-(benzoylamino)-2-deoxyhexopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6-tetra-O-acetyl-2-(benzoylamino)-2-deoxyhexopyranose(10385-49-6)
• EPA Substance Registry System: 1,3,4,6-tetra-O-acetyl-2-(benzoylamino)-2-deoxyhexopyranose(10385-49-6)

Safety Data

• Hazardous Substances Data: 10385-49-6(Hazardous Substances Data)

Usage

Chemical structure

A hexose sugar molecule with acetyl and benzoyl groups at various positions.

Derived from

Natural sugars found in nature.

Common use

Organic synthesis and carbohydrate chemistry.

Ability

Mimic natural sugar structures and interactions.

Specific structure

Valuable tool for studying carbohydrate-protein interactions.

Synthesis

Used for the synthesis of glycosylated compounds.

Potential applications

Pharmaceutical or biological applications.

Upstream product

• 10380-87-7 2-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline 
• 17460-45-6 tetra-acetyl glucosamine 
• 14131-63-6 D-glucosamine hydrochloride 
• 90176-39-9 2-benzylideneamino-2-deoxy-β-D-glucopyranose 
• 52162-39-7 2-(benzylidene)amino-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 65-85-0 benzoic acid 
• 7597-81-1 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-β-D-glucopyranose 
• 98-88-4 benzoyl chloride 

Downstream Products

• 72348-55-1 allyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-acetyl-2-benzamido-2-deoxy-β-D-glucopyranosyl)-α-D-galactopyranoside 
• 72348-54-0 propyl 2-acetamido-4,6-di-O-benzyl-2-deoxy-3-O-(3,4,6-tri-O-acetyl-2-benzamido-2-deoxy-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 58510-55-7 1,2:3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-acetyl-2-benzamido-2-deoxy-β-D-glucopyranosyl)-α-D-galactopyranose 
• 72366-34-8 allyl 3,4,6-tri-O-acetyl-2-benzamido-2-deoxy-β-D-glucopyranoside 
• 10380-87-7 2-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline 
• 53840-59-8 O³,O⁴,O⁶-triacetyl-2-benzoylamino-α-D-2-deoxy-glucopyranosyl chloride 
• 1273127-99-3 2-benzamido-2-deoxy-β-D-glucopyranosyl N,N-dimethyldithiocarbamate 
• 72348-53-9 allyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoyl)-2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 72333-19-8 propyl 2-acetamido-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 72333-20-1 allyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 6863-90-7 Methyl 2-benzamido-2-deoxy-α-D-glucopyranoside 
• 655-42-5 N-benzoylglucosamine 

Relevant articles and documents

Glucosamide compound and preparation and application thereof

The invention relates to a glucosamide compound and a preparation method thereof. The glucosamide compound has a structure as shown in the formula (I). In the formula (I), R is methoxy group, nitro group, amino-group, hydroxyl group, C1-4 alkyl group or halogen, n is the number of substituent groups, and n is 1 or 2. The glucosamide compound is simple to prepare, has excellent plant induced resistance activity, and can be used as a plant induced resistance agent for controlling cucumber bacterial angular leaf spot, cucumber target leaf spot and tomato late blight. The invention also relates to a plant induced resistant agent containing the compound.

Protected glycosides and disaccharides of 2-amino-2-deoxy-D-glucopyranose by ferric chloride-catalyzed coupling.

The ferric chloride-catalyzed glycosylation of hydroxy compounds by protected 2-acylamino-2-deoxy-beta-D-glucopyranose 1-acetates is described. In addition to known glycosides from the reaction of alcohols with 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-beta-D-glucopyranose (3), ally (and other alkyl) beta-glycosides were obtained from the N-benzoyl, N-phenoxyacetyl, N-methoxyacetyl, N-chloroacetyl, and N-phthaloyl congeners of 3. The latter compounds, except for the N-phthaloyl derivative, gave oxazolines in the absence of an alcoholic reactant. Compound 3 and the related N-benzoyl, N-chloroacetyl, N-acetyl-3,4,6-tri-O-benzyl, and N-acetyl-4-O-acetyl-3,6-di-O-benzyl derivatives were coupled to one or more protected sugars to form protected, beta-linked disaccharides. Coupling at the 6-positions of acceptors proceeded smoothly and gave 67-80% yields. For successful coupling at positions 3 and 4, long reaction times and multiple additions of glycosyl donor were required, and yields ranged from 60% to as low as 30%. 1,3,4,6-Tetra-O-acetyl-2-(chloroacetamido)-2-deoxy-beta-D- glucopyranose appeared to be the most reactive glycosyl donor in this series. The reaction of 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)[2,1- d]-2-oxazoline (derived from 3) with allyl alcohol was catalyzed by ferric chloride, and oxazolines were detected as intermediates in some of the glycosylations of protected sugars.