13343-67-4

Basic information

• Product Name: BENZYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• Synonyms: BENZYL GLCNAC;BENZYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;BENZYL 2-ACETAMIDO-2-DEOXY-SS-D-GLUCOPYRANOSIDE
• CAS NO: 13343-67-4
• Molecular Formula: C₁₅H₂₁NO₆
• Molecular Weight: 311.33
• Product Categories: Carbohydrates & Derivatives
• Mol File: 13343-67-4.mol
• Article Data: 37

Chemical Properties

• Melting Point: 183-198°C
• Boiling Point: 594.855 °C at 760 mmHg
• Flash Point: 313.557 °C
• Appearance: White solid
• Refractive Index: 1.59
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Heated)
• CAS DataBase Reference: BENZYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(13343-67-4)
• EPA Substance Registry System: BENZYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(13343-67-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13343-67-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C15H21NO6/c1-9(18)16-12-14(20)13(19)11(7-17)22-15(12)21-8-10-5-3-2-4-6-10/h2-6,11-15,17,19-20H,7-8H2,1H3,(H,16,18)/t11?,12-,13+,14+,15+/m0/s1

Upstream product

• 117177-19-2 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 10375-65-2 benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 74034-09-6 2-acetamido-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-glucitol 
• 4710-88-7 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl bromide hydrobromide 
• 62098-31-1 benzyl 3,4,6-tri-O-acetyl-2-amino-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 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 1040191-33-0 N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide 
• 51533-00-7 2-acetylamino-3,4,6-triacetyl-2-deoxy-α-D-glucopyranosyl bromide 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 

Downstream Products

• 120903-68-6 N-[(2S,3R,4R,5S,6R)-2-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-3-yl]-acetamide 
• 139893-41-7 N-[(2R,4aR,6R,7R,8R,8aS)-6-Benzyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 
• 250734-79-3 Acetic acid (2R,3R,4S,5R,6R)-2-((2R,3R,4R,5S,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 250734-81-7 Acetic acid (2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 250734-61-3 Acetic acid (2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 250734-83-9 Acetic acid (2S,3R,4S,5R,6R)-2-[(2R,3R,4R,6R)-3-acetylamino-2-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-oxo-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 250734-77-1 Acetic acid (2R,3R,4S,5R,6R)-2-[(2R,4aR,6R,7R,8R,8aS)-7-acetylamino-6-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 13320-00-8 benzyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 189683-17-8 Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,3S,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl)-6-methyl-tetrahydro-pyran-3-yl ester 
• 19374-64-2 N-((4aR,6R,7R,8S,8aS)-6-Benzyloxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 

Relevant articles and documents

Synthesis of Bacterial-Derived Peptidoglycan Cross-Linked Fragments

Peptidoglycan (PG) is the core structural motif of the bacterial cell wall. Fragments released from the PG serve as fundamental recognition elements for the immune system. The structure of the PG, however, encompasses a variety of chemical modifications among different bacterial species. Here, the applicability of organic synthetic methods to address this chemical diversity is explored, and the synthesis of cross-linked PG fragments, carrying biologically relevant amino acid modifications and peptide cross-linkages, is presented using solution and solid phase approaches.

Synthesis and antimicrobial activity of 6-sulfo-6-deoxy-D-glucosamine and its derivatives

6-Sulfo-6-deoxy-D-glucosamine (GlcN6S), 6-sulfo-6-deoxy-D-glucosaminitol (ADGS) and their N-acetyl and methyl ester derivatives have been synthesized and tested as inhibitors of enzymes catalyzing reactions of the UDP-GlcNAc pathway in bacteria and yeasts

Chemoenzymatic Synthesis of 4-Fluoro-N-Acetylhexosamine Uridine Diphosphate Donors: Chain Terminators in Glycosaminoglycan Synthesis

Unnatural uridine diphosphate (UDP)-sugar donors, UDP-4-deoxy-4-fluoro-N-acetylglucosamine (4FGlcNAc) and UDP-4-deoxy-4-fluoro-N-acetylgalactosamine (4FGalNAc), were prepared using both chemical and chemoenzymatic syntheses relying on N-acetylglucosamine-