108032-93-5

Basic information

• Product Name: Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside
• Synonyms: (+)-Phenyl 1-Thio-a-D-mannopyranoside Tetraacetate;Phenyl2,3,4,6-tetra-O-acetyl-a-D-thiomannopyranoside;(+)-Phenyl 1-Thio-α-D-mannopyranoside Tetraacetate;Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-α-D-mannopyranoside;Phenyl-2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranosid;Phenyl 2,3,4,6-tetra-O-acetyl-alpha-D-thiomannopyranoside;(+)-Phenyl 1-Thio-α;α-D-Mannopyranoside, phenyl 1-thio-2,3,4,6-tetraacetate
• CAS NO: 108032-93-5
• Molecular Formula: C₂₀H₂₄O₉S
• Molecular Weight: 440.46
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Sulfur & Selenium Compounds;Carbohydrates
• Mol File: 108032-93-5.mol
• Article Data: 177

Chemical Properties

• Melting Point: 85°C(lit.)
• Appearance: /
• Solubility: Chloroform, Ethyl Acetate, Methanol
• CAS DataBase Reference: Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside(108032-93-5)
• EPA Substance Registry System: Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside(108032-93-5)

Safety Data

• Hazardous Substances Data: 108032-93-5(Hazardous Substances Data)

Usage

Description

Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside is a chemical compound that serves as a mannose analog. It is a colorless oil with unique chemical properties that make it useful in various applications, particularly as an inhibitor of α-mannosidase.

Uses

Used in Pharmaceutical Industry:
Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside is used as an inhibitor of α-mannosidase for its potential role in the treatment of various diseases. As a mannose analog, it can interfere with the activity of α-mannosidase, an enzyme involved in the processing of glycoproteins and oligosaccharides. Inhibition of this enzyme may have therapeutic benefits in conditions where abnormal glycosylation occurs, such as in certain genetic disorders or cancer.
Used in Research and Development:
In the field of research and development, Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside is used as a valuable tool for studying the function and role of α-mannosidase in biological processes. Its ability to inhibit the enzyme allows scientists to investigate the consequences of α-mannosidase inhibition on cellular processes and the potential development of new therapeutic strategies.
Used in Drug Design and Synthesis:
Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside is also utilized in the design and synthesis of new drugs targeting α-mannosidase. Its unique chemical structure can be modified or used as a starting point for the development of more potent and selective inhibitors, which could lead to the creation of novel therapeutic agents for various diseases.

Upstream product

• 14365-16-3 bis-(phenylthio)-dibutylstannane 
• 604-68-2 α-D-glucopyranose peracetylate 
• 108-98-5 thiophenol 
• 930-69-8 sodium thiophenolate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 2872-65-3 p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 19879-84-6 tetraacetyl thioglucose 
• 98-80-6 phenylboronic acid 
• 2280-44-6 D-Glucose 
• 108-24-7 acetic anhydride 
• 604-69-3 β-D-glucose pentaacetate 
• 882-33-7 diphenyldisulfane 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 696-62-8 para-iodoanisole 

Downstream Products

• 13992-15-9 phenyl-1-thio-α-D-glucopyranoside 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 107961-09-1 α-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 108681-43-2 phenylsulfonyl 2,3,4,6-tetra-O-acetyl-1-deoxy-α-D-mannopyranoside 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 171283-83-3 2-(trimethylsilyl)ethyl 2-zido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 172364-19-1 4-methylumbelliferyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>3)-2-O-benzyl-4,6-benzylidene-β-D-glucopyranoside 
• 439-03-2 2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 174193-94-3 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1[*]3)-1-O-acetyl-2,4,6-tri-O-benzoyl-β-D-galactopyranose 
• 439-03-2 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl fluoride 
• 4163-45-5 2,3,4,6-tetra-O-acetyl-β-galactopyranosyl fluoride 

Relevant articles and documents

Conformational Distortion Using a Molecular Lever: Synthesis and Conformational Studies of Galactoside Derivatives

Novel bicyclic d-galactose derivatives containing a molecular lever were synthesized and their conformations studied by 1H-NMR and crystallography. Increasing the bulkiness in the alkylidene ring in combination with introducing bulky O-protective groups on the pyranoside ring, causes a ring flip from a 4C1 into the axial rich 1C4 conformation. With less bulky protective groups, the pyranoside ring resides in the 4C1 conformation despite distortion of the external alkylidene ring.

Total Syntheses of Conjugation-Ready Trisaccharide Repeating Units of Pseudomonas aeruginosa O11 and Staphylococcus aureus Type 5 Capsular Polysaccharide for Vaccine Development

Pseudomonas aeruginosa belongs to the group of three "critical priority" multi-drug-resistant pathogens listed by WHO and is responsible for severe and often deadly infections such as bloodstream infections and pneumonia. Staphylococcus aureus is also a "high priority" pathogen which is a major cause of serious nosocomial infections such as bacteremia, sepsis, and endocarditis. Owing to their ability to adapt resistance to almost any antibiotics, vaccines against these pathogens are urgently required. These pathogens express structurally unique and densely functionalized glycans on their surfaces which are absent on the host cells. Such carbohydrate antigens are valuable targets for the development of glycoconjugate vaccines and diagnostics. Here, we report the first total synthesis of the conjugation-ready trisaccharide repeating unit of Pseudomonas aeruginosa O11 via a highly stereoselective and efficient assembly of a rare l-fucosamine- A nd d-fucosamine-containing 1,2-cis-linked disaccharide motif and its regioselective glycosylation at O3. A systematic study was conducted for the notoriously difficult glycosylation with the most unreactive axial 4-OH of the rare disaccharide, and the successful outcome was utilized to accomplish the total synthesis of an aminopropyl linker-attached trisaccharide repeating unit of Staphylococcus aureus capsular polysaccharide type 5, which is also a potential antigen for immunotherapy and vaccine development. The judicious selection of protecting groups and reaction conditions allowed the stereoselective assembly and selective functional group interconversions to access the structurally complex linker-attached trisaccharide repeating units, which are valuable tools for immunological evaluation and vaccine development. The strategy is useful for the synthesis of other structurally related complex glycans.

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A generalized procedure for the one-pot preparation of glycosyl azides and thioglycosides directly from unprotected reducing sugars under phase-transfer reaction conditions

Per-O-acetylated glycosyl azides and thioglycosides were prepared in excellent yield directly from unprotected reducing sugars through in situ generation of per-O-acetylated glycosyl bromides by a generalized one-pot procedure under phase-transfer conditions. Stereoselective products were formed with complete inversion at the anomeric centers of the glycosyl bromides to provide a general high-yielding procedure for the preparation of 1,2-trans-glycosyl azides and thioglycosides. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Glycosylation of Glaucocalyxin a and Evaluation of Its Cytotoxic Activity

The 7,14-diglucoside of glaucocalyxin A was prepared by a five-step reaction. Its structure was confirmed by spectroscopic methods, and its cytotoxic activity was tested by the MTT method.

Iodine and its interhalogen compounds: Versatile reagents in carbohydrate chemistry v. synthesis of 1,2-trans-linked 1-thioglycosides from the per-o-acetylated glycoses

Treatment of per-O-acetylated mono- and di-saccharides with (alkyl/arylthio)trimethylsilane and iodine at ambient temperature results in the formation of the corresponding 1,2-trans-1-thioglycosides in very high yield. In the case of higher boiling thiols such as ethanethiol, the reaction can be effectively carried out in the presence of the thiol itself instead of the silylated derivative, but the reaction is not stereospecific. Moreover, in the latter reactions a portion of the starting material remains unchanged even on prolonged reaction. With β-D-glucose pentaacetate (11) as the starting material, its epimerisation occurred during the reaction and therefore the recovered starting material was of α-D-configuration. In addition, the methyl disulphide-hexamethyldisilane system has been found to serve as an effective and cheaper alternative to the expensive (methylthio)-trimethylsilane.

Synthesis of thioglycosides in room temperature ionic liquid

An eco-friendly reaction for the preparation of thioglycosides has been developed using an ionic liquid as the solvent. Thioglycosides were obtained in excellent yields on treatment of per-O-acetylated sugar derivatives with thiols in the presence of boro

Sulfonic acid functionalized nano γ-Al2O3 catalyzed per-O-acetylated of carbohydrates

A simple and clean synthesis of per-O-acetylation carbohydrate derivatives has been accomplished by treatment of sugars with a stoichiometric quantity of acetic anhydride under solvent-free conditions in the presence of sulfonic acid functionalized nano γ-Al2O3 as an efficient and environmentally benign catalyst.

Odorless preparation of thioglycosides and Thio-Michael adducts of carbohydrate derivatives

A general, odorless, one-pot methodology has been developed for the preparation of 1,2-trans-thioglycosides and thio-Michael addition products of carbohydrate derivatives through triphenyl phosphine-mediated cleavage of disulfides and reaction of the thio

Total Synthesis of a Partial Structure from Arabinogalactan and Its Application for Allergy Prevention

Arabinogalactan, a microheterogeneous polysaccharide occurring in plants, is known for its allergy-protective activity, which could potentially be used for preventive allergy treatment. New treatment options are highly desirable, especially in a preventive manner, due to the constant rise of atopic diseases worldwide. The structural origin of the allergy-protective activity of arabinogalactan is, however, still unclear and isolation of the polysaccharide is not feasible for pharmaceutical applications due to a variation of the activity of the natural product and contaminations with endotoxins. Therefore, a pentasaccharide partial structure was selected for total synthesis and subsequently coupled to a carrier protein to form a neoglycoconjugate. The allergy-protective activity of arabinogalactan could be reproduced with the partial structure in subsequent in vivo experiments. This is the first example of a successful simplification of arabinogalactan with a single partial structure while retaining its allergy-preventive potential.

Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides

The assembly of complex bacterial glycans presenting rare structural motifs and cis-glycosidic linkages is significantly obstructed by the lack of knowledge of the reactivity of the constituting building blocks and the stereoselectivity of the reactions i