14146-27-1

Basic information

• Product Name: benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside
• Synonyms: benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside
• CAS NO: 14146-27-1
• Molecular Weight: 401.459
• Mol File: 14146-27-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside(14146-27-1)
• EPA Substance Registry System: benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside(14146-27-1)

Safety Data

• Hazardous Substances Data: 14146-27-1(Hazardous Substances Data)

Usage

Description

Benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside is a complex chemical compound with a molecular formula of C26H27NO6. It is a derivative of alpha-D-glucopyranoside, a type of sugar, and features an intricate structure with multiple functional groups. benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside is used in organic chemistry and biochemistry research as a building block for the synthesis of other compounds and as a model for studying carbohydrate metabolism and structure-activity relationships. Its potential as a therapeutic agent makes it a valuable tool for understanding the role of carbohydrates in biological processes and for developing new drugs and materials.

Uses

Used in Organic Chemistry Research:
Benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside is used as a building block for the synthesis of other compounds, allowing researchers to create new molecules with specific properties and functions.
Used in Biochemistry Research:
benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside serves as a model for studying carbohydrate metabolism, providing insights into how carbohydrates are processed and utilized within biological systems.
Used in Structure-Activity Relationship Studies:
Benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside is used to investigate the relationship between the structure of a compound and its biological activity, which is crucial for the development of new drugs and materials.
Used in Drug Development:
Due to its potential as a therapeutic agent, benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside is used in the development of new drugs targeting various diseases and conditions, particularly those related to carbohydrate metabolism and its associated pathways.
Used in Material Science:
benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside's functional groups and complex structure make it a valuable component in the development of new materials with specific properties, such as improved biocompatibility or enhanced reactivity.

Upstream product

• 67398-54-3 benzyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 14146-26-0 benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 108-20-3 di-isopropyl ether 
• 66026-10-6 N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide 
• 13343-63-0 benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 55287-54-2 3,4-di-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside 
• 55287-49-5 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 38416-56-7 3,4,6-tri-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside 
• 38660-64-9 benzyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-di-O-mesyl-α-D-glucopyranoside 
• 162843-31-4 benzyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-(2-hydroxyethyl)-α-D-glucopyranoside 
• 75869-82-8 benzyl 2-acetamido-3-O-benzyl-2-deoxy-α-D-galactopyranoside 
• 112289-54-0 benzyl 2-acetamido-4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-α-D-galactopyranoside 
• 112289-53-9 benzyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-di-O-mesyl-α-D-galactopyranoside 
• 77396-73-7 benzyl 2-acetamido-4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 77356-41-3 benzyl 2-acetamido-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 70209-54-0 Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(β-D-galactopyranosyl)-α-D-glucopyranosid 
• 58700-48-4 Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranosid 
• 50908-12-8 benzyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-tosyl-α-D-glucopyranoside 
• 50908-14-0 benzyl 2-acetamido-3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside 

Relevant articles and documents

Methods for synthesis of alpha-d-gal (1~>3) gal-containing oligosaccharides

This invention relates to reagents and methods for synthesis of biologically active di- and tri-saccharides comprising α-D-Gal(1→3)-D-Gal. In particular the invention provides novel reagents, intermediates and processes for the solution or solid phase synthesis of α-D-galactopyranosyl-(1→3)-D-galactose, and derivatives thereof. In one preferred embodiments the invention provides a protected monosaccharide building block of general formula (II): in which R3 is methoxy or methyl; R1 is H, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl; and R2 is H, Fmoc, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl.

Preparation of O-Hydroxyethyl and O-Hydroxypropyl Derivatives of D-Glucose and 2-Acetamido-2-deoxy-D-glucose for Studies of Modified Hyaluronic Acid

Some hydroxyethyl and hydroxypropyl derivatives of D-glucose and of 2-acetamido-2-deoxy-D-glucose have been sunthesized for use as reference substances for structural studies of hydroxyethylated and hydroxypropylated hyaluronic acid.Hydroxyethyl and hydroxypropyl substituents were introduced in the 2-O- or 3-O-position of D-glucose and in the 4-O- or 6-O-positions of 2-acetamido-2-deoxy-D-glucose by reaction of suitably protected sugars with either ethylene oxide or propylene oxide.For hydroxyethyl derivatives yields varied between 21 and 74percent and with a substantial portion of the doubly alkylated compounds.For hydroxypropyl derivatives yields varied between 15 and 80percent.Only trace amounts of the doubly alkylated compounds were found.The proportions of the respective derivatives were estimated using GLC-MS.All products were characterized by 1H and 13C NMR spectroscopy.

Synthesis of carbohydrate analogs (positional, configurational, and optical) of n-acetylmuramoyl-L-alanyl-D-isoglutamine, and their immunoadjuvant activities.

2-Acetamido-2-deoxy-4- and -6-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-glucopyranose, 2-acetamido-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-allopyranose, -D-gulopyranose, -D-galactopyranose, -D-mannopyranose, and -L-idopyranose, and 3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D- and -L-glucopyranose were synthesized, in order to clarify the structural requirements for the immunoadjuvant activity of the carbohydrate moiety in N-acetylmuramoyl-L-alanyl-D-isoglutamine. Immunoadjuvant activity of the N-acetylmuramoyl-dipeptide analogs was examined in guinea-pigs.