10353-00-1

Basic information

• Product Name: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-[(trichloroacetyl)amino]hexopyranose
• CAS NO: 10353-00-1
• Molecular Formula: C₁₆H₂₀Cl₃NO₁₀
• Molecular Weight: 492.6897
• Mol File: 10353-00-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 551.9°C at 760 mmHg
• Flash Point: 287.6°C
• Density: 1.47g/cm³
• Vapor Pressure: 3.15E-12mmHg at 25°C
• Refractive Index: 1.519
• CAS DataBase Reference: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-[(trichloroacetyl)amino]hexopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-[(trichloroacetyl)amino]hexopyranose(10353-00-1)
• EPA Substance Registry System: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-[(trichloroacetyl)amino]hexopyranose(10353-00-1)

Safety Data

• Hazardous Substances Data: 10353-00-1(Hazardous Substances Data)

Usage

Chemical structure

A derivative of glucose with acetyl and trichloroacetyl groups attached to its hydroxyl groups.

Functional groups

Contains acetyl and trichloroacetyl groups.

Application

Used in biochemical research and organic synthesis.

Importance

Important for studying the structure and function of carbohydrates, as well as for developing new pharmaceuticals and chemical compounds.

Modification

Useful for modifying other molecules and studying their interactions with biological systems.

Fields of use

Valuable tool for researchers in biochemistry, organic chemistry, and pharmaceutical development.

Upstream product

• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 76-02-8 trifluoroacetyl chloride 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 52162-39-7 2-(benzylidene)amino-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 14131-63-6 D-glucosamine hydrochloride 
• 90176-39-9 2-benzylideneamino-2-deoxy-β-D-glucopyranose 
• 51471-40-0 2--2-deoxy-D-glucopyranose 
• 114297-26-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(4-methoxyphenyl)methylidene]amino}-D-glucopyranose 
• 4124-31-6 trichloroacetic acid anhydride 
• 7597-81-1 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-β-D-glucopyranose 
• 51471-40-0 6-(hydroxymethyl)-3-[4-methoxybenzylideneamino]tetrahydropyran-2,4,5-triol 
• 108-24-7 acetic anhydride 

Downstream Products

• 169557-87-3 phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside 
• 273400-77-4 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 
• 765910-16-5 tert-butyldimethylsilyl 6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside 
• 765910-17-6 tert-butyldimethylsilyl 4-O-benzoyl-6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside 
• 765910-18-7 4-O-benzoyl-6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-α-D-glucopyranosyl trichloroacetimidate 
• 399036-28-3 C₆₅H₆₀Cl₃NO₂₂ 
• 399036-29-4 allyl O-(2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 
• 399036-13-6 allyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 
• 273400-79-6 4-methoxyphenyl 2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 
• 273400-82-1 4-methoxyphenyl 2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 273400-86-5 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 273400-80-9 4-methoxyphenyl 2-deoxy-3,6-di-O-pivaloyl-2-trichloroacetamido-β-D-glucopyranoside 
• 371123-22-7 phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 
• 915154-77-7 C₄₆H₅₁N₃O₁₄ 

Relevant articles and documents

Synthesis and Structure-Activity Relationship Study of Antimicrobial Auranofin against ESKAPE Pathogens

Auranofin, an FDA-approved arthritis drug, has recently been repurposed as a potential antimicrobial agent; it performed well against many Gram-positive bacteria, including multidrug resistant strains. It is, however, inactive toward Gram-negative bacteria, for which we are in dire need of new therapies. In this work, 40 auranofin analogues were synthesized by varying the structures of the thiol and phosphine ligands, and their activities were tested against ESKAPE pathogens. The study identified compounds that exhibited bacterial inhibition (MIC) and killing (MBC) activities up to 65 folds higher than that of auranofin, making them effective against Gram-negative pathogens. Both thiol and the phosphine structures influence the activities of the analogues. The trimethylphosphine and triethylphosphine ligands gave the highest activities against Gram-negative and Gram-positive bacteria, respectively. Our SAR study revealed that the thiol ligand is also very important, the structure of which can modulate the activities of the AuI complexes for both Gram-negative and Gram-positive bacteria. Moreover, these analogues had mammalian cell toxicities either similar to or lower than that of auranofin.

Total Synthesis of a Densely Functionalized Plesiomonas shigelloides Serotype 51 Aminoglycoside Trisaccharide Antigen

Plesiomonas shigelloides, a pathogen responsible for frequent outbreaks of severe travelers' diarrhea, causes grave extraintestinal infections. Sepsis and meningitis due to P. shigelloides are associated with a high mortality rate as antibiotic resistance increases and vaccines are not available. Carbohydrate antigens expressed by pathogens are often structurally unique and are targets for developing vaccines and diagnostics. Here, we report a total synthesis of the highly functionalized trisaccharide repeating unit 2 from P. shigelloides serotype 51 from three monosaccharides. A judicious choice of building blocks and reaction conditions allowed for the four amino groups adorning the sugar rings to be installed with two N-acetyl (Ac) groups, rare acetamidino (Am), and d-3-hydroxybutyryl (Hb) groups. The strategy for the differentiation of amino groups in trisaccharide 2 will serve well for the syntheses of other complex glycans.