14040-20-1

Basic information

• Product Name: BENZYL 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• Synonyms: 2-Acetamido-1,3-di-O-benzyl-4,6-O-benzylidene-2-deoxy-b-D-glucopyranoside;Benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy--D-glucopyranoside;PhenylMethyl 2-(AcetylaMino)-2-deoxy-3-O-(phenylMethyl)-4,6-O-(phenylMethylene)-β-D-glucopyranoside
• CAS NO: 14040-20-1
• Molecular Formula: C₂₉H₃₁NO₆
• Molecular Weight: 0
• Product Categories: Carbohydrates & Derivatives;Aromatics;Heterocycles
• Mol File: 14040-20-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 257°C dec.
• Appearance: /
• Refractive Index: 1.613
• Solubility: Hot DMF, Hot THF
• Stability: Store in Freezer
• CAS DataBase Reference: BENZYL 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(14040-20-1)
• EPA Substance Registry System: BENZYL 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(14040-20-1)

Safety Data

• Hazardous Substances Data: 14040-20-1(Hazardous Substances Data)

Usage

Description

BENZYL 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is a white solid that serves as a synthetic intermediate in the field of carbohydrate and oligosaccharide synthesis. It is a complex organic compound with a unique structure that allows for the creation of various carbohydrate derivatives.

Uses

Used in Pharmaceutical Industry:
BENZYL 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is used as a synthetic intermediate for the development of carbohydrate-based pharmaceuticals. Its unique structure enables the synthesis of complex carbohydrate molecules that can be used as therapeutic agents or for the development of new drugs targeting specific biological pathways.
Used in Chemical Research:
In the field of chemical research, BENZYL 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is used as a key intermediate for the synthesis of various complex carbohydrates and oligosaccharides. Researchers can utilize this compound to explore the chemical properties and potential applications of these carbohydrate derivatives.
Used in Material Science:
BENZYL 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE can also be used in material science for the development of novel materials with specific properties. The compound's unique structure can be exploited to create materials with tailored characteristics, such as improved biocompatibility or enhanced mechanical properties.
Used in Food Industry:
In the food industry, BENZYL 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE can be used as a synthetic intermediate for the development of new additives or ingredients with specific functional properties. These properties may include improved taste, texture, or shelf-life, contributing to the overall quality and appeal of food products.
Used in Cosmetics Industry:
BENZYL 2-ACETAMIDO-3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE can be employed in the cosmetics industry as a synthetic intermediate for the development of new formulations with enhanced properties. The compound's unique structure can be used to create innovative products with improved skin hydration, anti-aging effects, or other beneficial properties for personal care applications.

InChI:InChI=1/C29H31NO6/c1-20(31)30-25-27(32-17-21-11-5-2-6-12-21)26-24(19-34-28(36-26)23-15-9-4-10-16-23)35-29(25)33-18-22-13-7-3-8-14-22/h2-16,24-29H,17-19H2,1H3,(H,30,31)/t24?,25-,26+,27+,28?,29+/m0/s1

Upstream product

• 13343-61-8 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 10375-65-2 benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 100-51-6 benzyl alcohol 
• 3055-51-4 benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 81749-53-3 benzyl 3-O-allyl-2-benzamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 3554-91-4 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside 
• 35812-81-8 Benzyl-2-amino-2-desoxy-α-D-mannopyranosid 
• 10380-86-6 phenylmethyl 2-acetylamino-2-deoxy-α-D-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 95451-93-7 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide 
• 95451-81-3 Benzyl-2-azido-2-desoxy-α-D-mannoopyranosid 
• 68733-20-0 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside 

Downstream Products

• 62867-63-4 benzyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-β-D-glucopyranoside 
• 95451-84-6 benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid 
• 62867-64-5 benzyl 2-acetamido-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

Syntheses of model oligosaccharides of biological significance. XII. Synthesis, NMR, and conformational analysis of trideuteriomethyl 4-O-(β-D-mannopyranosyl)-2-acetamido-2-deoxy-β-D-glucopyranoside: the use of DEPT 1H to 13C transfer for T1 measurements and NOE assignments of ...

The title disaccharide Manp(β1-4)GlcpNAcβ1-OCD3 has been prepared by a short synthetic sequence through the inversion of configuration from gluco to manno involving benzyl Glcp(β1-4)GlcpNAc.The disaccharide was subjected to detailed high-field 1H and 13C NMR study.First, conventional and 2D spectra were run to afford a complete set of assigned spectral parameters.Next, steady-state 1H- NOE and 1H, 13C spin lattice relaxation experiments were performed to infer dynamic spectral data related to molecular conformation.Owing to tight couplings and signal overlaps in the 1H spectrum, proton relaxation and selected NOE data were obtained via 13C NMR after transfer of the actual, non-equilibrium, proton magnetization to the 13C frequency domain.Using this experimental approach it has been found that T1's for Manp H-4 and GlcpNAc H-2 were substantially longer than those of the other sugar ring protons, and that the principal interresidue dipolar contact in Manp(β1-4)GlcpNAcβ1-OCD3 takes place between Manp H-1 and GlcpNAc H-4.Subsequently, a conformational analysis of the disaccharide was executed by means of a semiempirical method comparing Boltzman-averaged computed observables with experimental T1 and NOE values.The results suggest that the disaccharide has substantial conformational flexibility.Its exo-anomeric-stabilized conformational minimum at approximately Φ = +50 deg (Ψ = 0 +/- 10 deg) of the glycosidic rotational angle is significantly populated but this global minimum does not represent the only rotational form available to the molecule.

N-Allyl and N-benzyl derivatives of 2-amino-2-deoxy-D-glucose

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The synthesis of 2-acetamido-2-deoxy-4-O-beta-D-mannopyranosyl-D-glucose.

Condensation of 4,6-di-O-acetyl-2,3-O-carbonyl-alpha-D-mannopyranosyl bromide with 2-amino-2-N,3-O-carbonyl-5.6-O-isopropylidene-D-glucose diethyl acetal gave, unexpectedly, 2-amino-2-N,3-O-carbonyl-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-O-carbonyl-alpha-D-mannopyranosyl)-5,6-O-isopropylidene-D-glucose diethyl acetal, futher transformed, by de-esterification followed by acetylation, into the previously known 2-amino-2-N,3-O-carbonyl-2-deoxy-5,6-O-isopropylidene-4-O-alpha-D-mannopyranosyl-D-glucose diethyl acetal and its tetra-O-acetyl derivative. Benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside was condensed with 2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranosyl bromide to give benzyl 2-acetamido-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside. Removal of the 2-O-acetyl group, followed by oxidation with acetic anhydridedimethyl sulfoxide, gave a beta-D-arabino-hexosid-2-ulose (25). After reduction with sodium borohydride, removal of the benzyl groups gave crystalline 2-acetamido-2-deoxy-4-O-beta-D-mannopyranosyl-D-glucose (27). The anomeric configuration of the glycosidic linkage was ascertained by comparison with the alpha-D-linked disaccharide.