92420-89-8

Basic information

• Product Name: 3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSE 1,2-(METHYL ORTHOACETATE)
• Synonyms: 2,3,4-Tri-O-acetyl-a-D-glucuronide methyl ester trichloroacetimidate;Methyl 2,3,4-tri-O-acetyl-1-O-trichloroacetimidoyl-alpha-D-glucopyranosyluronate min. 99%;2,3,4-tri-O-acetyl-1-(2,2,2-trichloroethanimidate)-α-D-glucopyranuronic acid methyl ester;3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSE 1,2-(METHYL ORTHOACETATE);Methyl2,3,4-tri-O-acetyl-a-D-glucopyranosyluronosyltrichloroacetimidate;2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester, Trichloroacetimidate;Methyl-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl Trichloroacetimidate)uronate;(2S,3S,4S,5R,6R)-2-(Methoxycarbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS NO: 92420-89-8
• Molecular Formula: C₁₅H₁₈Cl₃NO₁₀
• Molecular Weight: 478.663
• Product Categories: Carbohydrates & Derivatives;Intermediates;13C & 2H Sugars
• Mol File: 92420-89-8.mol
• Article Data: 27

Chemical Properties

• Melting Point: 103-105°C
• Boiling Point: 442.115°C at 760 mmHg
• Flash Point: 221.183°C
• Appearance: /
• Density: 1.595g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 1.39±0.70(Predicted)
• Stability: Acid Sensitive, Temperature Sensitive
• CAS DataBase Reference: 3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSE 1,2-(METHYL ORTHOACETATE)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSE 1,2-(METHYL ORTHOACETATE)(92420-89-8)
• EPA Substance Registry System: 3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSE 1,2-(METHYL ORTHOACETATE)(92420-89-8)

Safety Data

• Hazardous Substances Data: 92420-89-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C15H18Cl3NO10/c1-5(20)25-8-9(26-6(2)21)11(27-7(3)22)13(28-10(8)12(23)24-4)29-14(19)15(16,17)18/h8-11,13,19H,1-4H3/t8-,9-,10?,11-,13+/m0/s1

Upstream product

• 3082-95-9 1α-hydroxy-2,3,4-triacetyl-α-D-glucopyranuronate methyl ester 
• 545-06-2 trichloroacetonitrile 
• 3082-96-0 methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate 
• 77668-10-1 2,3,4-tri-O-acetyl-β-D-glucuronic acid methyl ester 
• 5432-32-6 methyl 1,2,3,4-tetraacetyl-α-D-glucopyranuronate 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 82228-14-6 methyl D-glucopyranuronate 
• 63-29-6 D-glucurono-6,3-lactone 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 72692-06-9 methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 

Downstream Products

• 168286-97-3 O²,O³,O⁴-triacetyl-O¹-(2-oxo-2H-chromen-7-yl)-β-D-glucopyranuronic acid methyl ester 
• 55331-64-1 cyclohexyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid methyl ester 
• 224964-33-4 allyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 619328-21-1 pent-4-enyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranoside 
• 488092-65-5 methyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside 
• 864160-21-4 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[2-(benzyl-methyl-amino)-propyl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 824967-47-7 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-((2R,3S,4R,5R,6S)-2-acetoxymethyl-5-azido-4-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 824967-48-8 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-((2R,3S,4R,5R,6R)-2-acetoxymethyl-5-azido-4-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 915207-11-3 4-[5-((2S,3R,4S,5S,6S)-3,4,5-Triacetoxy-6-methoxycarbonyl-tetrahydro-pyran-2-yloxy)-pyridin-2-yl]-piperazine-1-carboxylic acid benzyl ester 
• 72692-06-9 methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 
• 619328-22-2 pent-4-enyl 4,6-O-benzylidene-2-deoxy-2-N-acetyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranoside 
• 1093679-73-2 Caffeic acid-3-O-glucuronide 
• 1093679-71-0 Caffeic acid 4-O-glucuronide 
• 1093679-68-5 C₂₄H₂₈O₁₃ 

Relevant articles and documents

Studies in sugar chemistry VII. Glucuronides of podophyllum derivatives

The antitumor activities of several glucuronide methyl esters of podophyllum derivatives were tested in vitro against two human tumor cell lines and their drug resistant sublines. The most active compound studied was methyl (4'-carbobenzoxy-4'-demethyl- epipodophyllotoxin-D-glucopyranoside)uronate 19. Compound 19 was as potent in a colon carcinoma model and was twice as potent in a lung carcinoma model as etoposide 6. In vivo, however, in a mouse leukemia P388 model, it had only marginal activity, with a maximum T/C% value of 125 at 37 mg/kg (iv).

Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**

Despite many years of invention, the field of carbohydrate chemistry remains rather inaccessible to non-specialists, which limits the scientific impact and reach of the discoveries made in the field. Aiming to increase the availability of stereoselective

Extended scaffold glucuronides: En route to the universal synthesis of O -aryl glucuronide prodrugs

We demonstrate that an extended scaffold based on a self-immolative linker (SIL) enables the universal production of O-aryl glucuronide prodrugs: high yield glucuronidation is performed on a precursor substrate (SIL) and the subsequent drug conjugation proceeds via less challenging chemical reactions.

Synthesis of 3′-deoxy-3′-fluorothymidine (FLT) 5′-O-glucuronide: A reference standard for imaging studies with [ 18F]FLT

Reaction of methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-d- glucopyranuronate with 3′-deoxy-3′-fluorothymidine in the presence of trimethylsilyl trifluoromethanesulfonate gave (2R,3R,4S,5S,6S)-2-(((2R,3S,5R) -3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl) tetrahydrofuran-2-yl)methoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4, 5-triyl triacetate, which was hydrolysed to 3′-deoxy-3′- fluorothymidine-5′-glucuronide. Analysis of this reference standard by high performance liquid chromatography enabled the identification of [ 18F]3′-deoxy-3′-fluorothymidine-5′-glucuronide in blood samples from six human patients who had been administered [ 18F]3′-deoxy-3′-fluorothymidine.