55722-49-1

Basic information

• Product Name: Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside
• Synonyms: Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside;Ethyl2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside;Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose;Ethyl 1-thio-beta-D-galactopyranoside tetraacetate;Ethyl 1-thio-beta-D-galactopyranoside-2,3,4,6-tetraacetate;Ethyl 1-thiogalactopyranosidetetraacetate;Ethyl-2,3,4,6-tetraacetyl--L-thiogalactopyranoside;Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside
• CAS NO: 55722-49-1
• Molecular Formula: C₁₆H₂₄O₉S
• Molecular Weight: 392.42136
• EINECS: 1533716-785-6
• Mol File: 55722-49-1.mol
• Article Data: 85

Chemical Properties

• Melting Point: 75℃
• Boiling Point: 453℃
• Flash Point: 213℃
• Appearance: /
• Density: 1.27
• CAS DataBase Reference: Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside(55722-49-1)
• EPA Substance Registry System: Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside(55722-49-1)

Safety Data

• Hazardous Substances Data: 55722-49-1(Hazardous Substances Data)

Usage

General Description

Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside is a synthetic compound used in biochemical and pharmaceutical research. It is commonly employed as a reagent in the synthesis of complex carbohydrates and glycoconjugates. Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside is a derivative of galactose, a monosaccharide sugar, and is modified with acetyl and thio groups, which can alter its properties and reactivity. Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside is often used in the study and development of drugs, vaccines, and diagnostics targeting carbohydrate structures, and it serves as a valuable tool in the exploration of biological processes involving carbohydrates and glycoconjugates.

Upstream product

• 75-08-1 ethanethiol 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 83-87-4 D-Mannose pentaacetate 
• 7647-01-0 hydrogenchloride 
• 3458-28-4 D-Mannose 
• 811-51-8 sodium thioethylate 
• 19879-84-6 O²,O³,O⁴,O⁶-Tetraacetyl-1-thio-D-glucose 
• 75-03-6 ethyl iodide 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 136758-06-0 ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-rhamnopyranoside 
• 127753-95-1 ethyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 

Downstream Products

• 13121-61-4 tetra-O-acetyl-1,5-anhydro-D-mannitol 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 7473-36-1 (2R,3R,4S,5S,6R)-2-Ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 56245-60-4 ethyl 1-thio-β-D-galactopyranoside 
• 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 
• 125520-03-8 3,4,6-Tri-O-acetyl-α-D-galactopyranose 1,2-(methyl-3,6-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosid-4-yl-orthoacetate) 

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.