52645-73-5

Basic information

• Product Name: ETHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE
• Synonyms: ETHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE;ETHYL 2,3,4,6-TETRA-O-ACETYL-B-D-1-THIOGLUCOPYRANOSIDE;ETHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-THIOGLUCOPYRANOSIDE;ETHYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-1-THIOGLUCOPYRANOSIDE;Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-glucopyranoside;.beta.-D-Glucopyranoside, ethyl 1-thio-, tetraacetate;ETHYL 2,3,4,6-TETRA-O-ACETYL-SS-D-THIOGLUCOPYRANOSIDE;Ethyl 2,3,4,6-tetra-O-acetyl-alpha-D-thioglucopyranoside
• CAS NO: 52645-73-5
• Molecular Formula: C₁₆H₂₄O₉S
• Molecular Weight: 392.42
• EINECS: 1533716-785-6
• Product Categories: Carbohydrates & Derivatives
• Mol File: 52645-73-5.mol
• Article Data: 62

Chemical Properties

• Melting Point: 78-79 °C
• Boiling Point: 453.2 °C at 760 mmHg
• Flash Point: 212.6 °C
• Appearance: /
• Density: 1.27 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: ETHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE(52645-73-5)
• EPA Substance Registry System: ETHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE(52645-73-5)

Safety Data

• Hazardous Substances Data: 52645-73-5(Hazardous Substances Data)

Usage

Description

ETHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE is a white crystalline solid that serves as a crucial reagent in the synthesis of glucosides. Its unique chemical structure allows for versatile applications across various industries.

Uses

Used in Pharmaceutical Industry:
ETHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE is used as a key reagent for the preparation of glucosides, which are essential in the development of various pharmaceutical compounds. These glucosides can be utilized in the synthesis of drugs targeting specific diseases and conditions, making this compound a valuable asset in the pharmaceutical sector.
Used in Chemical Research:
As a white crystalline solid with distinct chemical properties, ETHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE is also used in chemical research for studying the properties and reactions of glucosides. This helps researchers gain a deeper understanding of the underlying chemistry and potentially discover new applications for these compounds.
Used in Food Industry:
In the food industry, ETHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE can be used as a reagent for the synthesis of glucosides that serve as additives or enhancers in the production of various food products. These glucosides can improve the taste, texture, or shelf life of the final product, making this compound an important tool in the food industry.
Used in Cosmetics Industry:
ETHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE is also used in the cosmetics industry for the preparation of glucosides that can be incorporated into skincare and beauty products. These glucosides may have moisturizing, anti-aging, or other beneficial properties, making this compound a valuable ingredient in the development of cosmetics.

Upstream product

• 75-08-1 ethanethiol 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl iodide 
• 530-26-7 D-Mannose 
• 108-24-7 acetic anhydride 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 83-87-4 D-Mannose pentaacetate 
• 3458-28-4 D-Mannose 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 811-51-8 sodium thioethylate 
• 4490-94-2 3,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-[(ethoxycarbothioyl)sulfanyl] tetrahydro-2H-pyran-4-yl-acetate 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 2280-44-6 D-Glucose 
• 1419178-02-1 C₂₀H₄₄O₄SSi₂ 
• 492-61-5 β-D-glucose 

Downstream Products

• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 118627-56-8 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 139921-55-4 Methyl 4-O-benzoyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 139921-54-3 Methyl 4-O-benzoyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-L-rhamnopyranoside 
• 137438-91-6 C₅₀H₄₆O₁₆ 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside 
• 155814-72-5 (2R,3S,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 105376-04-3 ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 
• 38992-99-3 methyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 151123-93-2 Ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-glucopyranoside 
• 151072-56-9 2-O-Benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-glucopyranosyl chloride 
• 151072-57-0 Methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-glucopyranoside 
• 151123-94-3 Ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-1-thio-α-D-glucopyranoside 

Relevant articles and documents

Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions

A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.

A versatile approach to the synthesis of glycans containing mannuronic acid residues

Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3-O-picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linkedviaβ-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3-O-benzoyl group is also reported.

Chemical glucosylation of pyridoxine

The chemical synthesis of pyridoxine-5′-β-D-glucoside (5′-β-PNG) was investigated using various glucoside donors and promoters. Hereby, the combination of α4,3-O-isopropylidene pyridoxine, glucose vested with different leaving and protecting groups and the application of stoichiometric amounts of different promoters was examined with regards to the preparation of the twofold protected PNG. Best results were obtained with 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl fluoride and boron trifluoride etherate (2.0 eq.) as promoter at 0 °C (59%). The deprotection was accomplished stepwise with potassium/sodium hydroxide in acetonitrile/water followed by acid hydrolysis with formic acid resulting in the chemical synthesis of 5′-β-PNG.