62860-10-0

Basic information

• Product Name: 1-Thio-alpha-D-glucopyranose pentaacetate
• Synonyms: [(2R,3R,4S,5R,6R)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-acetylsulfanyl-oxan-4-yl] acetate;2,3,4,6-Tetra-o-acetyl-1-S-acetyl-1- thio- glucopyranose;1-Thio-alpha-D-glucopyranose pentaacetate;α-D-pentaacetatethio Glucopyranose;AcGlcSAc
• CAS NO: 62860-10-0
• Molecular Formula: C₁₆H₂₂O₁₀S
• Molecular Weight: 406.41
• Mol File: 62860-10-0.mol
• Article Data: 32

Chemical Properties

• Melting Point: 121-122 °C
• Boiling Point: 468.1°Cat760mmHg
• Flash Point: 222.3°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 6.17E-09mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: 1-Thio-alpha-D-glucopyranose pentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Thio-alpha-D-glucopyranose pentaacetate(62860-10-0)
• EPA Substance Registry System: 1-Thio-alpha-D-glucopyranose pentaacetate(62860-10-0)

Safety Data

• Hazardous Substances Data: 62860-10-0(Hazardous Substances Data)

Usage

General Description

1-Thio-alpha-D-glucopyranose pentaacetate is a chemical compound that is structurally derived from glucose. It is a sulfur-containing sugar derivative with five acetyl groups attached to the glucose molecule. 1-Thio-alpha-D-glucopyranose pentaacetate is commonly used as a reagent in organic synthesis, particularly in the field of carbohydrate chemistry. It has also been studied for its potential applications in drug development and as a building block for the synthesis of more complex organic molecules. The acetyl groups on the molecule improve its solubility in organic solvents and make it a valuable tool for chemical reactions in a variety of laboratory settings.

InChI:InChI=1/C16H22O10S/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(26-12)27-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15-,16-/m1/s1

Upstream product

• 19879-84-6 O²,O³,O⁴,O⁶-Tetraacetyl-1-thio-D-glucose 
• 108-24-7 acetic anhydride 
• 5207-08-9 bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)disulfide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 10387-40-3 potassium thioacetate 
• 507-09-5 tiolacetic acid 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 75-36-5 acetyl chloride 
• 160621-19-2 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 47537-23-5 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiourea 
• 22566-82-1 1-deoxy-1-thio-D-glucopyranose 

Downstream Products

• 55474-17-4 Sodium; (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-thiolate 
• 119803-58-6 C₄₉H₅₇IO₂₅S 
• 119803-57-5 p-iodophenyl-2,3,6-tri-O-acetyl-4-O-<2,3-di-O-acetyl-6-O-benzoyl-4-S-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-4-thio-β-D-glucopyranosyl>-α-D-glucopyranoside 
• 140654-55-3 triphenylmethyl 2,3,6-tri-O-benzoyl-4-S-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1,4-dithio-α-D-glucopyranoside 
• 62778-20-5 sodium salt of 1-thio-α-D-glucopyranose 
• 161016-86-0 methyl 2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside 
• 191485-96-8 methyl 2,3,6-tri-O-benzyl-4-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-thio-β-D-glucopyranoside 
• 22566-82-1 1-thio-β-D-glucopyranose 

Relevant articles and documents

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.

Preparation method and application of peracetyl-protected 1-thioglucose and glucose 1-mercaptan

The invention belongs to the technical field of medicine and sugar chemical synthesis, and particularly relates to a preparation method and application of peracetyl-protected 1-thioglucose and glucose1-mercaptan. The preparation method comprises the following steps of reacting peracetyl-protected glucose and potassium thioacetate in an organic solvent at the temperature of between normal temperature and 50 DEG C under the catalysis of boron trifluoride diethyl ether for 4-8 hours to obtain peracetyl-protected 1-thioglucose; and dissolving the prepared peracetyl-protected 1-thioglucose in dimethylformamide, and removing thioacetyl by using hydrazine hydrate to obtain peracetyl-protected glucose 1-mercaptan. The peracetyl-protected glucose 1-mercaptan can be used for further preparing auronofen and gliclazide thioglycoside analogues. The method disclosed by the invention is mild in reaction condition, simple and convenient to operate, low in synthesis cost, relatively green and high inyield, the auronofen is a medicine for treating rheumatic arthritis, and the gliflozin thioglycoside analogue is a potential medicine for treating type 2 diabetes mellitus.

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.