41670-79-5

Basic information

• Product Name: ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE
• Synonyms: ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE;ETHYL 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-THIOGLUCOPYRANOSIDE;Ethyl 2,3,4,6-Tetra-O-acetyl-b-D-thioglucopyranoside;Ethyl 2,3,4,6-Tetra-O-acetyl--D-thioglucopyranoside;(2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(ethylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS NO: 41670-79-5
• Molecular Formula: C₁₆H₂₄O₉S
• Molecular Weight: 392.42
• Product Categories: Carbohydrates & Derivatives
• Mol File: 41670-79-5.mol
• Article Data: 62

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE(41670-79-5)
• EPA Substance Registry System: ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE(41670-79-5)

Safety Data

• Hazardous Substances Data: 41670-79-5(Hazardous Substances Data)

Usage

Description

ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE is a chemical compound that serves as a versatile reagent in the synthesis of various glycosides and glucosides. It is characterized by its acetylated structure, which plays a crucial role in its reactivity and applications in organic chemistry.

Uses

Used in Organic Chemistry:
ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE is used as a reagent for the preparation of glycosides, which are essential in the synthesis of complex carbohydrates and their derivatives. Its acetylated structure allows for selective deprotection and glycosidic bond formation, making it a valuable tool in carbohydrate chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE is used as a reagent for the preparation of glucosides, which are important in the development of drugs targeting various biological processes. Glucosides can act as prodrugs, enhancing the bioavailability and efficacy of active pharmaceutical ingredients.
Used in Research and Development:
ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE is also used in research and development for the study of carbohydrate-based compounds and their interactions with biological systems. Its reactivity and ease of synthesis make it a preferred choice for exploring the structure-activity relationships of glycosides and their potential applications in medicine and other fields.

Upstream product

• 75-08-1 ethanethiol 
• 604-69-3 β-D-glucose pentaacetate 
• 75-03-6 ethyl iodide 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 572-09-8 Acetic acid (2R,3R,4S)-3,5-diacetoxy-2-acetoxymethyl-6-bromo-tetrahydro-pyran-4-yl ester 
• 3366-47-0 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose 
• 6207-30-3 2,3:4,5-di-O-isopropylidene-D-glucose diethyl dithioacetal 
• 60405-34-7 6-O-benzoyl-2,3:4,5-di-O-isopropylidene-D-glucose diethyl dithioacetal 
• 1379587-24-2 O-(2,3:4,5-di-O-isopropylidene-β-D-glucoseptanosyl) trichloroacetimidate 
• 1379587-23-1 ethyl 1-thio-2,3:4,5-di-O-isopropylidene-α-D-glucoseptanoside 
• 108-24-7 acetic anhydride 
• 1290085-45-8 2,3:4,5-di-O-isopropylidene-β-D-glucoseptanose 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 212192-83-1 ethyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside 
• 187152-88-1 ethyl 4,6-di-O-benzyl-1-thio-α-D-mannopyranoside 
• 129750-23-8 Ethyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 
• 3879-79-6 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 
• 71526-33-5 methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 116113-70-3 isopropyl-O-2,3,4,6-tetra-O-benzyl-β-D-mannopyranose 
• 116113-69-0 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-isopropoxytetrahydro-2H-pyran 
• 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 

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.

Beta-D-glucose short-chain fatty acid ester compound as well as preparation method and application thereof

The invention discloses a beta-D-glucose short-chain fatty acid ester compound as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The compound is a compound shown as a formula I, or a stereoisomer, a pharmaceutically acceptable salt, a solvate or a prodrug of the compound shown as the formula I. The formula is as shown in the description, wherein R is a methyl group, an ethyl group, a propyl group, a propylene group, an isopropylidene group, a butyl group, a butylidene group, an isobutylidene group, an amyl group, a pentylidene group or an isoamylidene group. The compound has potential prevention and treatment effects on diabetes, hyperlipidemia, atherosclerosis, Alzheimer's disease, cardiovascular and cerebrovascular diseases,inflammation, tumors and depression.

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.