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 
• 23716-85-0 tri-n-butyltin(SC₂H₅) 
• 83-87-4 D-Mannose pentaacetate 
• 108-24-7 acetic anhydride 
• 7647-01-0 hydrogenchloride 
• 3458-28-4 D-Mannose 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl iodide 
• 530-26-7 D-Mannose 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 75-03-6 ethyl iodide 
• 7296-15-3 alpha-D-mannopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 

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 
• 144606-21-3 C₄₂H₅₄O₂₄ 
• 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 

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.

A versatile approach to the synthesis of mannosamine glycosides

O-Picoloyl protecting groups at remote positions can affect the stereoselectivity of glycosylation by means of the H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O-picoloyl group at the C-3 position of a mannosamine donor can provide high or complete stereocontrol. The method was also utilized for the synthesis of a biologically relevant trisaccharide related to the capsular polysaccharide of Streptococcus pneumoniae serotype 4. Also reported herein is a method to achieve complete α-manno stereoselectivity with mannosamine donors equipped with 3-O-benzoyl group. This journal is