3068-34-6

Basic information

• Product Name: 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSYL CHLORIDE 3,4,6-TRIACETATE
• Synonyms: 1-CHLORO-2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOSE;2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSYL CHLORIDE 3,4,6-TRIACETATE;2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSYL CHLORIDE;2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL CHLORIDE;ALPHA-ACETOCHLORO-D-GLUCOSAMINE;ACETOCHLORO-ALPHA-D-GLUCOSAMINE;CHLORO-2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSE;(2R,3S,4R,5R,6R)-5-(Acetylamino)-2-[(acetyloxy)methyl]-6-chlorotetrahydro-2H-pyran-3,4-diyl diacetate,2-Acetamido-2-deoxy-alpha-D-glucopyranosyl chloride 3,4,6-triacetate
• CAS NO: 3068-34-6
• Molecular Formula: C₁₄H₂₀ClNO₈
• Molecular Weight: 365.76
• EINECS: 221-325-6
• Product Categories: Substrates;13C & 2H Sugars;Aminosugars;Biochemistry;Glucose;Halogenosugars;O-Substituted Sugars;Sugars;Carbohydrates & Derivatives
• Mol File: 3068-34-6.mol
• Article Data: 86

Chemical Properties

• Melting Point: >214 °C (dec.)(lit.)
• Boiling Point: 516.4 °C at 760 mmHg
• Flash Point: 266.1 °C
• Appearance: /
• Density: 1.32
• Vapor Pressure: 9E-11mmHg at 25°C
• Refractive Index: 117.5 ° (C=1, CHCl3)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• PKA: 13.22±0.70(Predicted)
• Stability: Stablizied with 2% Calcium Carbonate
• CAS DataBase Reference: 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSYL CHLORIDE 3,4,6-TRIACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSYL CHLORIDE 3,4,6-TRIACETATE(3068-34-6)
• EPA Substance Registry System: 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSYL CHLORIDE 3,4,6-TRIACETATE(3068-34-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 3068-34-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Chloro 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose (cas# 3068-34-6) is a useful reactant in the total synthesis of glycosylated human interferon-γ.

InChI:InChI=1/C14H20ClNO8/c1-6(17)16-11-13(23-9(4)20)12(22-8(3)19)10(24-14(11)15)5-21-7(2)18/h10-14H,5H2,1-4H3,(H,16,17)

Upstream product

• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 75-36-5 acetyl chloride 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 75-09-2 dichloromethane 
• 7732-18-5 water 
• 108-24-7 acetic anhydride 
• 90-76-6 2-deoxy-2-amino glucose 
• 75-34-3 1,1-dichloroethane 
• 14131-63-6 D-glucosamine hydrochloride 
• 14131-68-1 N-acetyl-D-glucosamine 
• 66-84-2 D-(+)-glucosamine hydrochloride 
• 70749-28-9 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 

Downstream Products

• 2771-48-4 methyl 2-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranoside 
• 13089-27-5 p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 50271-51-7 N-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside 
• 76155-50-5 ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 121356-12-5 [1]naphthyl-(tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranoside) 
• 115893-22-6 (2-methoxy-benzyl)-(tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranoside) 
• 111570-99-1 (4-acetyl-phenyl)-(tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranoside) 
• 13089-26-4 o-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 13089-21-9 1-O-phenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose 
• 10034-19-2 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose hydrochloride 
• 28446-21-1 N-acetylglucosamine-1-phosphate 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 112485-12-8 benzyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 7772-86-3 tert-butyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

Genetically Introducing Biochemically Reactive Amino Acids Dehydroalanine and Dehydrobutyrine in Proteins

Expansion of the genetic code with unnatural amino acids (Uaas) has significantly increased the chemical space available to proteins for exploitation. Due to the inherent limitation of translational machinery and the required compatibility with biological settings, function groups introduced via Uaas to date are restricted to chemically inert, bioorthogonal, or latent bioreactive groups. To break this barrier, here we report a new strategy enabling the specific incorporation of biochemically reactive amino acids into proteins. A latent bioreactive amino acid is genetically encoded at a position proximal to the target natural amino acid; they react via proximity-enabled reactivity, selectively converting the latter into a reactive residue in situ. Using this Genetically Encoded Chemical COnversion (GECCO) strategy and harnessing the sulfur-fluoride exchange (SuFEx) reaction between fluorosulfate-l-tyrosine and serine or threonine, we site-specifically generated the reactive dehydroalanine and dehydrobutyrine into proteins. GECCO works both inter- and intramolecularly, and is compatible with various proteins. We further labeled the resultant dehydroalanine-containing protein with thiol-saccharide to generate glycoprotein mimetics. GECCO represents a new solution for selectively introducing biochemically reactive amino acids into proteins and is expected to open new avenues for exploiting chemistry in live systems for biological research and engineering.

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Radical-Mediated Acyl Thiol-Ene Reaction for Rapid Synthesis of Biomolecular Thioester Derivatives

The thiol-ene ‘click’ reaction has emerged as a versatile process for carbon–sulfur bond formation with widespread applications in chemical biology, medicinal chemistry and materials science. Thioesters are key intermediates in a wide range of synthetic and biological processes and efficient methods for their synthesis are of considerable interest. Herein, we report the first examples of acyl-thiol-ene (ATE) for the synthesis of biomolecular thioesters, including peptide, lipid and carbohydrate derivatives. A key finding is the profound effect of the amino acid side chain on the outcome of the ATE reaction. Furthermore, radical generated thioesters underwent efficient S-to-N acyl transfer and desulfurisation to furnish ‘sulfur-free’ ligation products in an overall amidation process with diverse applications for chemical ligation and bioconjugation.

Rapid access to Asp/Glu sidechain hydrazides as thioester precursors for peptide cyclization and glycosylation

Head-to-sidechain macrocylic peptides, and neoglycopeptides, were readily prepared by site-specific amidation of aspartic and glutamic acid sidechain hydrazides. Hydrazides, serving as latent thioesters, were introduced through regioselective opening of the corresponding Nα-Fmoc protected anhydride precursors.

Novel hymexazol oxyglycoside conjugate as well as preparation and application thereof

The invention discloses a preparation method and application of a novel hymexazol oxyglycoside conjugate bactericide. Galactose, mannose, glucose, mannosamine, galactosamine, glucosamine, N-acetyl-galactosamine, N-acetyl-mannosamine and acetylglucosamine are respectively conjugated with hymexazol to obtain a series of hymexazol oxyglycoside conjugates. The structural general formula of the compound is shown as I, R is hydroxyl, oxyacetyl, amino and acetamido, and R1 is hydrogen and acetyl. The conjugate disclosed by the invention is novel in structure, has good solubility and antifungal activity, and has the potential of becoming a novel green bactericide.