13639-50-4

Basic information

• Product Name: 1-thio-beta-D-glucose pentaacetate
• Synonyms: 1-(Acetylthio)-1-deoxy-β-D-glucopyranose tetraacetate;1-S-Acetyl-2-O,3-O,4-O,6-O-tetraacetyl-1-thio-β-D-glucopyranose;1-Thio-β-D-glucopyranose 1,2,3,4,6-pentaacetate;1-Thio-β-D-glucopyranose pentaacetate;Acetyl 2-O,3-O,4-O,6-O-tetraacetyl-1-thio-β-D-glucopyranoside;Thioacetic acid S-(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl) ester;Nsc409737;1-thio-beta-D-glucose pentaacetate
• CAS NO: 13639-50-4
• Molecular Formula: C₁₆H₂₂O₁₀S
• Molecular Weight: 496.48128
• EINECS: 237-128-3
• Mol File: 13639-50-4.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 468.1°Cat760mmHg
• Flash Point: 222.3°C
• Appearance: /
• Density: 1.32g/cm³
• CAS DataBase Reference: 1-thio-beta-D-glucose pentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-thio-beta-D-glucose pentaacetate(13639-50-4)
• EPA Substance Registry System: 1-thio-beta-D-glucose pentaacetate(13639-50-4)

Safety Data

• Hazardous Substances Data: 13639-50-4(Hazardous Substances Data)

Usage

General Description

1-thio-beta-D-glucose pentaacetate is a chemical compound derived from glucose that has been modified to include a thio group and five acetate groups. 1-thio-beta-D-glucose pentaacetate is commonly used in organic chemistry and biochemistry research as a synthetic precursor for studying the reactivity and properties of carbohydrates. It is often utilized in the synthesis of complex carbohydrates and as a building block for the creation of other sugar derivatives. Due to its specific structure, 1-thio-beta-D-glucose pentaacetate has potential applications in drug development and other fields where carbohydrate chemistry is important.

Upstream product

• 108-24-7 acetic anhydride 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 10387-40-3 potassium thioacetate 
• 604-69-3 β-D-glucose pentaacetate 
• 83-87-4 D-glucose pentaacetate 
• 50-99-7 D-glucose 
• 10593-29-0 sodium 1-thio-β-D-glucopyranoside 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 507-09-5 tiolacetic acid 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 19879-84-6 tetraacetyl thioglucose 
• 6586-65-8 3,4,6-tri-O-acetyl-D-galactal 
• 52485-06-0 3,4,6-tri-O-acetyl-D-glucal 
• 2280-44-6 D-Glucose 

Downstream Products

• 55474-17-4 Sodium; (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-thiolate 
• 10593-29-0 sodium 1-thio-β-D-glucopyranoside 

Relevant articles and documents

Improved Synthesis of 1-Glycosyl Thioacetates and Its Application in the Synthesis of Thioglucoside Gliflozin Analogues

An improved method to synthesize 1-glycosyl thioacetates was developed, where per-O-acetylated glycoses were allowed to directly react with potassium thioacetate (KSAc) in the presence of BF3 ? Et2O in ethyl acetate under mild conditions. This method not only overcomes the disadvantage of the traditional one-step method, which is that the odorous and toxic thioacetic acid has to be used, but also overcomes the disadvantage of the traditional two-step method, which is that the unstable intermediate, glycosyl halide, has to be synthesized from the per-O-acetylated glycose in advance. Based on this, the per-O-acetylated glucosyl disulfide and the per-O-acetylated glucosyl 1-thiol were efficiently synthesized in high yields (91 % and 90 % respectively) starting from per-O-acetylated glycoses in two-step without the need to isolate intermediate products. Through metal-catalyzed cross-coupling of per-O-acetylated glucosyl 1-thiol with aryl-iodide under very mild conditions, two thioglucoside gliflozin analogues were efficiently synthesized in high yields for the first time. These two thioglucoside gliflozin analogues were further confirmed to be stable to hydrolysis of β-glucosidase.

One pot synthesis of thio -glycosides via aziridine opening reactions

A one-pot aziridine opening reaction by glycosyl thiols generated in situ from the corresponding anomeric thio-acetates affords thio-glycosides with a pseudo-disaccharide structure and an N-linked tether. The scope of the one-pot aziridine opening reaction was explored on a series of mono- and disaccharides, creating a class of pseudo-glycosidic compounds with potential for further functionalization. Unexpected anomerization of glycosyl thiols was observed under the reaction conditions and the influence of temperature, base and solvent on the isomerization was investigated. Single isomers were obtained in good to acceptable yields for mannose, rhamnose and sialic acid derivatives. The class of thio-glycomimetics synthesized can potentially be recognized by various lectins, while presenting hydrolytic and enzymatic stability. The nitrogen functionality incorporated in the glycomimetics can be exploited for further functionalization, including tethering to linkers, scaffolds or peptide residues.

Modular Synthesis of Aryl Thio/Selenoglycosides via the Catellani Strategy

We described a novel palladium-catalyzed domino procedure for the preparation of (hetero)aryl thio/selenoglycosides. Readily available (hetero)aryl iodides and easily accessible 1-thiosugars/1-selenosugars are utilized as the substrates. Meanwhile, 10 types of sugars are quite compatible with this reaction with good regio- and stereoselectivity, high efficiency, and broad applicability (up to 89%, 53 examples). This method enables the straightforward formation of the C(sp2)-S/Se bond of (hetero)aryl thio/selenoglycosides.