126187-25-5

Basic information

• Product Name: ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGALACTOPYRANOSIDE
• Synonyms: ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGALACTOPYRANOSIDE;ETHYL 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-THIOGALACTOPYRANOSIDE;ETHYL 2,3,4,6-TETRA-O-ACETYL-SS-D-THIOGALACTOPYRANOSIDE;Ethyl 2,3,4,6-Tetra-O-acetyl-α-D-thiogalactopyranoside;Ethly-2,3,4,6-tetra-O-acetyl-α-D-thiogalactopyranoside;Ethyl 1-Thio-α-D-galactopyranoside 2,3,4,6-Tetraacetate;Ethyl 1-thio-alpha-D-galactopyranoside-2,3,4,6-tetraacetate;Ethyl 1-thio-alpha-D-galactopyranosidetetraacetate
• CAS NO: 126187-25-5
• Molecular Formula: C16H24O9S
• Molecular Weight: 392.42
• EINECS: 1533716-785-6
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 126187-25-5.mol
• Article Data: 63

Chemical Properties

• Melting Point: 67-68°C
• Boiling Point: 453℃
• Flash Point: 213℃
• Appearance: /
• Density: 1.27
• Vapor Pressure: 2.11E-08mmHg at 25°C
• Refractive Index: 1.501
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane, Ether, Ethyl Acetate, Methanol
• CAS DataBase Reference: ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGALACTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGALACTOPYRANOSIDE(126187-25-5)
• EPA Substance Registry System: ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGALACTOPYRANOSIDE(126187-25-5)

Safety Data

• Hazardous Substances Data: 126187-25-5(Hazardous Substances Data)

Usage

Description

ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGALACTOPYRANOSIDE is a white powder chemical compound that serves as a valuable reagent in the synthesis of galactosides.

Uses

Used in Pharmaceutical Industry:
ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGALACTOPYRANOSIDE is used as a reagent for the preparation of galactosides, which are essential in the development of pharmaceutical compounds targeting the galactose-binding sites of various biological molecules.
Used in Organic Chemistry Research:
ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGALACTOPYRANOSIDE is used as a key intermediate in organic chemistry research for the synthesis of complex organic molecules, particularly those involving galactose derivatives.
Used in Biochemical Analysis:
ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGALACTOPYRANOSIDE is used as a reference compound in biochemical analysis to study the interactions between galactosides and their respective binding proteins or receptors, aiding in the understanding of biological processes and the development of targeted therapies.

InChI:InChI=1/C16H24O9S/c1-6-26-16-15(24-11(5)20)14(23-10(4)19)13(22-9(3)18)12(25-16)7-21-8(2)17/h12-16H,6-7H2,1-5H3

Upstream product

• 145259-92-3 C₃₄H₅₀O₈SSi₂ 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 75-08-1 ethanethiol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 152488-30-7 ethyl 2,3-O-isopropylidene-1-thio-β-L-rhamnopyranoside 
• 4490-94-2 3,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-[(ethoxycarbothioyl)sulfanyl] tetrahydro-2H-pyran-4-yl-acetate 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 127753-95-1 ethyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 75-03-6 ethyl iodide 
• 2280-44-6 D-Glucose 
• 108-24-7 acetic anhydride 
• 604-69-3 β-D-glucose pentaacetate 

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 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 192935-99-2 ethyl 2-O-acetyl-4,6-O-benzylidene-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 

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.

Developing a library of mannose-based mono-and disaccharides: A general chemoenzymatic approach to monohydroxylated building blocks

Regioselective deprotection of acetylated mannose-based mono-and disaccharides differently functionalized in anomeric position was achieved by enzymatic hydrolysis. Candida rugosa lipase (CRL) and Bacillus pumilus acetyl xylan esterase (AXE) were immobilized on octyl-Sepharose and glyoxyl-agarose, respectively. The regioselectivity of the biocatalysts was affected by the sugar structure and functionalization in anomeric position. Generally, CRL was able to catalyze regioselective deprotection of acetylated monosaccharides in C6 position. When acetylated disaccharides were used as substrates, AXE exhibited a marked preference for the C2, or C6 position when C2 was involved in the glycosidic bond. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently monohydroxylated building blocks that could be used as intermediates for the synthesis of mannosylated glycoconjugate vaccines targeting mannose receptors of antigen presenting cells.