32934-24-0

Basic information

• Product Name: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside
• Synonyms: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside
• CAS NO: 32934-24-0
• Molecular Weight: 392.427
• Mol File: 32934-24-0.mol
• Article Data: 62

Chemical Properties

• CAS DataBase Reference: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside(32934-24-0)
• EPA Substance Registry System: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside(32934-24-0)

Safety Data

• Hazardous Substances Data: 32934-24-0(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 75-08-1 ethanethiol 
• 604-69-3 β-D-glucose pentaacetate 
• 152488-30-7 ethyl 2,3-O-isopropylidene-1-thio-β-L-rhamnopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 7647-01-0 hydrogenchloride 
• 3458-28-4 D-Mannose 
• 83-87-4 D-Mannose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 23716-85-0 tri-n-butyltin(SC₂H₅) 
• 83-87-4 β-D-mannopyranose 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 

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 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 117252-67-2 2-(Trimethylsilyl)ethyl-<2,3,4,6-tetra-O-acetyl-α-D-mannopyranosid> 
• 488744-04-3 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-prop-2-ynyloxycarbonyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-3-yl ester 
• 140428-83-7 2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 680573-14-2 2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 680573-18-6 2-azidoethyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1→2)-3,4,6-tri-O-benzoyl-α-D-mannopyranoside 

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.