125354-48-5

Basic information

• Product Name: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside
• Synonyms: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside
• CAS NO: 125354-48-5
• Molecular Weight: 392.427
• Mol File: 125354-48-5.mol
• Article Data: 62

Chemical Properties

• CAS DataBase Reference: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside(125354-48-5)
• EPA Substance Registry System: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside(125354-48-5)

Safety Data

• Hazardous Substances Data: 125354-48-5(Hazardous Substances Data)

Upstream product

• 75-08-1 ethanethiol 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 7647-01-0 hydrogenchloride 
• 3458-28-4 D-Mannose 
• 530-26-7 D-Mannose 
• 108-24-7 acetic anhydride 
• 75-03-6 ethyl iodide 
• 83-87-4 D-Mannose pentaacetate 
• 7296-15-3 alpha-D-mannopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 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 

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 
• 5239-08-7 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-O-diisopropylidene-α-D-galactopyranose 
• 4860-78-0 6-O-acetyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 178628-92-7 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside S-oxide 
• 406946-95-0 ethyl 2,3,4,6-tetra-O-acetyl-S-(N-tosylimino)-1-thio-α-D-mannopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 216859-54-0 ethyl 2,3,4,6-tetra-O-acetyl-S-(N-tosylimino)-1-thio-β-D-glucopyranoside 

Relevant articles and documents

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Synthesis and cytotoxicities of icogenin analogues with disaccharide residues

For further structure-activity relationships (SAR) research of furostan saponin, two icogenin analogues: (25R)-22-O-methyl-furost-5-en-3β,26-diol-3-O-α-l-rhamnopyrano syl-(1 → 2)-β-d-glucopyranoside 1 and (25R)-22-O-methyl-furost-5-en-3β,26-diol-3-O-α-l-r

Synthesis of S-linked glycoconjugates and S-disaccharides by thiol-ene coupling reaction of enoses

Free-radical hydrothiolation of the endocyclic double bond of enoses is reported. Reaction between 2-acetoxy-D-glucal and a range of thiols including amino acid, peptide, glycosyl thiols, and sugars with primary or secondary thiol functions gave S-linked α-glucoconjugates and S-disaccharides with full regio- and stereoselectivity. Addition of glycosyl thiols to a 2,3-unsaturated glycoside also proceeded with good selectivity and afforded a series of 3-deoxy-S-disaccharides.

A Sugar-Based Gelator for Marine Oil-Spill Recovery

Marine oil spills constitute an environmental disaster with severe adverse effects on the economy and ecosystem. Phase-selective organogelators (PSOGs), molecules that can congeal oil selectively from oil–water mixtures, have been proposed to be useful for oil-spill recovery. However, a major drawback lies in the mode of application of the PSOG to an oil spill spread over a large area. The proposed method of using carrier solvents is impractical for various reasons. Direct application of the PSOG as a solid, although it would be ideal, is unknown, presumably owing to poor dispersion of the solid through the oil. We have designed five cheap and easy-to-make glucose-derived PSOGs that disperse in the oil phase uniformly when applied as a fine powder. These gelators were shown to selectively congeal many oils, including crude oil, from oil–water mixtures to form stable gels, which is an essential property for efficient oil-spill recovery. We have demonstrated that these PSOGs can be applied aerially as a solid powder onto a mixture of crude oil and sea water and the congealed oil can then be scooped out. Our innovative mode of application and low cost of the PSOG offers a practical solution to oil-spill recovery.

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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.