132413-50-4

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE is used as a chiral derivatizing reagent for the high-performance liquid chromatography (HPLC) analysis of enantiomeric purities. This application is vital for ensuring the quality and consistency of pharmaceutical compounds, as it allows for the accurate measurement of the purity of chiral molecules, which are essential in drug development and manufacturing.
Used in Chemical Analysis:
In the realm of chemical analysis, 2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE serves as a valuable tool for the determination of enantiomeric purities of various compounds, including amino acids, β-adrenergic blockers, and alkyloxiranes. Its use in HPLC allows for the precise identification and quantification of enantiomers, which is critical for understanding the stereochemistry and biological activity of these compounds.
Overall, 2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE is an indispensable reagent in the fields of pharmaceuticals and chemical analysis, providing a reliable method for assessing the enantiomeric purity of a wide range of compounds.

InChI:InChI=1/C35H27NO9S/c37-32(23-13-5-1-6-14-23)41-21-27-28(43-33(38)24-15-7-2-8-16-24)29(44-34(39)25-17-9-3-10-18-25)30(31(42-27)36-22-46)45-35(40)26-19-11-4-12-20-26/h1-20,27-31H,21H2/t27-,28-,29+,30-,31-/m1/s1

Upstream product

• 463-71-8 thiophosgene 
• 108967-43-7 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosylamine hydrobromide 
• 333-20-0 potassium thioacyanate 
• 61198-88-7 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide 
• 123956-66-1 2,3,4,6-tetra-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-β-D-galactopyranosylamine 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 158419-90-0 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl thiocyanate 
• 158419-88-6 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl thiocyanate 
• 22435-65-0 N-(2,2-diethoxycarbonylvinyl)-β-D-galactopyranosylamine 
• 98-88-4 benzoyl chloride 

Downstream Products

• 916801-58-6 N-[tetra(O-benzoyl)-β-D-glucopyranosyl] isocyanodichloride 
• 1304706-06-6 C₄₂H₃₅N₃O₉S 
• 1304706-02-2 tetra-O-benzoyl-β-D-glucopyranosyl thiosemicarbazide 
• 1304706-12-4 C₄₄H₄₀N₄O₉S 
• 1304706-10-2 C₄₂H₃₄ClN₃O₉S 
• 1304706-08-8 C₄₃H₃₇N₃O₁₀S 
• 1209466-38-5 C₄₁H₄₁N₃O₉S 
• 3376-24-7 N-tert-butyl-α-phenylnitrone 
• 108967-46-0 N,N'-bis-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)thiourea 
• 127293-22-5 5-methyl-1-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-4-imidazoline-2-thione 

Relevant academic research and scientific papers

Influence of bromide ions on the synthesis of anomeric thiocyanates

The synthesis of anomeric thiocyanates with the α- and β-configuration is described. Reactions performed under standard conditions afforded the 1,2-trans derivatives as the main products, whereas in the presence of the quaternary ammonium salts, the 1,2-c

Studies into the preparation of 1-deoxy-1-thiocyanato-D-glycopyranosyl cyanides and the anomeric effect of the thiocyanate group

The reaction of per-O-acetylated 1-bromo-1-deoxy-α-D-arabinopyranosyl cyanide with thiocyanate ions gave the corresponding 1-deoxy-1-thiocyanato-α- and β-D-arabinopyranosyl cyanides. In the reaction of the per-O-acetylated 1-bromo-1-deoxy-β-D-xylopyranosy

Reaction of sugar thiocyanates with Grignard reagents. New synthesis of thioglycosides

Glycosyl thiocyanates having hydroxyl groups protected with acetyl or benzoyl groups react readily at -40°C with Grignard reagents to afford the corresponding alkyl or aryl thioglycosides in good yields. Monosaccharide derivatives having the SCN grouping at other positions form under similar conditions thioethers. Axial thiocyanates do not react. Elevated temperatures induce side reactions leading to mercaptans.