6619-10-9

Basic information

• Product Name: 1,2,3,4-TETRA-O-ACETYL-6-O-TOSYL-BETA-D-GLUCOPYRANOSE
• Synonyms: 1,2,3,4-TETRA-O-ACETYL-6-O-TOSYL-BETA-D-GLUCOPYRANOSE;TETRA-O-ACETYL-6-O-TOSYL-BETA-D-GLUCOPYRANOSE;1,2,3,4-TETRA-O-ACETYL-6-O-TOSYL-SS-D-GLUCOPYRANOSE;1,2,3,4-Tetra-O-acetyl-6-O-(p-toluenesulfonyl)-b-D-glucopyranose
• CAS NO: 6619-10-9
• Molecular Formula: C₂₁H₂₆O₁₂S
• Molecular Weight: 502.49
• Mol File: 6619-10-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 574.8 °C at 760 mmHg
• Flash Point: 301.4 °C
• Appearance: /
• Density: 1.38 g/cm³
• Vapor Pressure: 3.25E-13mmHg at 25°C
• Refractive Index: 1.54
• CAS DataBase Reference: 1,2,3,4-TETRA-O-ACETYL-6-O-TOSYL-BETA-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRA-O-ACETYL-6-O-TOSYL-BETA-D-GLUCOPYRANOSE(6619-10-9)
• EPA Substance Registry System: 1,2,3,4-TETRA-O-ACETYL-6-O-TOSYL-BETA-D-GLUCOPYRANOSE(6619-10-9)

Safety Data

• Hazardous Substances Data: 6619-10-9(Hazardous Substances Data)

Usage

General Description

1,2,3,4-Tetra-O-Acetyl-6-O-Tosyl-Beta-D-Glucopyranose is a chemical compound that belongs to the family of glucopyranose derivatives. It is a highly acetylated form of D-glucopyranose, with four acetyl groups attached to the hydroxyl groups in the molecule, and a tosyl group attached to the sixth hydroxyl group. It is commonly used as a building block for the synthesis of various carbohydrate derivatives and glycoconjugates. The compound is mainly used in organic chemistry and biochemistry research for the modification and functionalization of carbohydrates. It is also used in the development of glycosylation agents and as a precursor for the preparation of glycosyl donors for glycosylation reactions. Additionally, it has potential applications in the field of medicinal chemistry for the development of new drugs and therapeutics.

InChI:InChI=1/C21H26O12S/c1-11-6-8-16(9-7-11)34(26,27)28-10-17-18(29-12(2)22)19(30-13(3)23)20(31-14(4)24)21(33-17)32-15(5)25/h6-9,17-21H,10H2,1-5H3

Upstream product

• 29907-22-0 O²,O³,O⁴-triacetyl-O⁶-(toluene-4-sulfonyl)-β-D-glucopyranosyl chloride 
• 563-63-3 silver(I) acetate 
• 64-19-7 acetic acid 
• 26275-20-7 6-deoxy-1,2-O-isopropylidene-6-(4'-methylbenzene)sulfonyloxy-D-glucofuranose 
• 2280-44-6 D-Glucose 
• 108-24-7 acetic anhydride 
• 98-59-9 p-toluenesulfonyl chloride 
• 50-99-7 D-glucose 
• 37074-90-1 1,2,3,4-tetra-O-acetyl-6-O-trityl-β-D-glucopyranose 
• 13100-46-4 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose 

Downstream Products

• 29907-22-0 O²,O³,O⁴-triacetyl-O⁶-(toluene-4-sulfonyl)-β-D-glucopyranosyl chloride 
• 55500-08-8 2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-α-D-glucopyranosyl bromide 
• 20113-43-3 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose 
• 7468-48-6 6-deoxy-6-iodotetra-O-acetyl-β-D-glucopyranose 
• 106192-41-0 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-β-D-glucopyranosyl azide 
• 1509923-70-9 [¹⁹F]6Glc-RGD 
• 778593-27-4 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-β-D-glucopyranosyl bromide 
• 189446-96-6 2,3,4-tri-O-benzoyl-1,6-dideoxy-1,6-epithio-β-D-glucopyranose 
• 923980-23-8 2,3,4-tri-O-acetyl-1-thio-6-O-tosyl-β-D-glucopyranose 
• 923980-28-3 2,4-di-O-benzoyl-1,6-anhydro-1-thio-β-D-glucopyranose 

Relevant articles and documents

Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates

The synthesis and characterization of a ‘complete set’ of positional isomers of tetrakis(perfluorophenyl)porphyrins (TFPP)-glucose conjugates (1OH, 2OH, 3OH, 4OH, and 6OH) are reported herein. The cellular uptake and photocytotoxicity of these conjugates were examined in order to investigate the influence of location of the TFPP moiety on the D-glucose molecule on the biological activity of the conjugates. An In vitro biological evaluation revealed that the certain of these isomers have a greater effect on cellular uptake and cytotoxicity than others. The TFPP-glucose conjugates 1OH, 3OH, and 4OH were found to exert exceptional photocytotoxicity in several types of cancer cells compared to 2OH and 6OH substituted isomers.

1,6-Anhydro-1-thio-β-D-glucopyranose (thiolevoglucosan) and the corresponding sulfoxides and sulfone

Starting 1,2,3,4-tetra-O-acetyl-6-O-tosyl-β-D-glucopyranose (3) was converted into 2,3,4-tri-O-acetyl-1-thio-6-O-tosyl-β-D-glucopyranose (6) via intermediate glycosyl bromide 4 and S-thiouronium salt 5. Treatment of compound 6 with sodium methoxide gave 1,6-anhydro-1-thio-β-D-glucopyranose (thiolevoglucosan 2a). The isomeric sulfoxides 7 and 8 were prepared by selective oxidation of thiolevoglucosan 2a with hydrogen peroxide or 3-chloroperoxybenzoic acid. The structure of new compounds was confirmed by 1H and 13C NMR spectroscopy or by X-ray analysis; magnetic anisotropy of the sulfinyl and sulfonyl group has been discussed.