158716-07-5

Usage

Uses

Used in Pharmaceutical Industry:
Phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside is used as a key intermediate in the synthesis of complex carbohydrates for various pharmaceutical applications. The compound's protecting groups facilitate the selective protection and deprotection of the carbohydrate, enabling the creation of intricate carbohydrate structures with potential therapeutic properties.
Used in Chemical Synthesis:
In the field of chemical synthesis, phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside is utilized as a versatile building block for the creation of complex carbohydrate structures. The compound's protecting groups allow for precise control over the synthesis process, enabling the development of novel carbohydrate-based compounds with potential applications in various industries.
Used in Research and Development:
Phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside is also employed in research and development, particularly in the study of carbohydrate chemistry and its applications in various fields. The compound's unique structure and protecting groups make it an invaluable tool for researchers working on the design and synthesis of complex carbohydrates and their potential applications in drug discovery, material science, and other areas.

Upstream product

• 158716-04-2 phenyl exo(phenyl)-2,3:4,6-di-O-benzylidene-1-thio-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 159407-19-9 phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 83-87-4 D-Mannose pentaacetate 
• 108-98-5 thiophenol 
• 121524-01-4 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside 
• 151763-69-8 phenyl 1-thio-D-mannopyranoside 

Downstream Products

• 159353-70-5 phenyl 2-O-p-methoxybenzyl-3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside 
• 848397-71-7 S-phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-(p-toluenesulfonyl)-α-D-thiomannopyranoside 
• 887471-11-6 phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside 
• 915221-35-1 phenyl 4,6-O-benzylidene-2-O-(3-naphthalen-1-yl-prop-2-ynyl)-3-O-benzyl-1-thio-α-D-mannopyranoside 
• 922183-05-9 phenyl 3-O-benzyl-4,6-O-benzylidene-3-2-O-(2,2-dimethyltrimethylene phosphornoyl)-α-D-thiomannopyranoside 
• 863297-03-4 (2R,4aR,6R,7R,8S,8aR)-6-Azido-8-benzyloxy-2-phenyl-7-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 863297-04-5 (2R,4aR,6S,7R,8S,8aR)-6-Azido-8-benzyloxy-2-phenyl-7-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 168138-13-4 (1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-hydroxy-3-butenyl>-2-phenyl-1,3-dioxane 
• 168138-12-3 (2R,4S)-4-[(1R,2R)-1-Benzyloxy-2-(4-methoxy-benzyloxy)-but-3-enyl]-2-phenyl-[1,3]dioxan-5-one 
• 172967-72-5 (1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-2-phenyl-1,3-dioxane 
• 168138-11-2 (1'R,2R,2'R,4R,5R)-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-5-hydroxy-2-phenyl-1,3-dioxane 
• 168254-34-0 (1'R,2R,2'R,4R,5S)-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-5-hydroxy-2-phenyl-1,3-dioxane 
• 168138-21-4 (1'R,2R,2'R,4R,5S)-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-5-hydroxy-2-phenyl-1,3-dioxane 
• 168138-20-3 (1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane 

Relevant academic research and scientific papers

Total Synthesis of Phospholipomannan of Candida albicans

First, total synthesis of the cell surface phospholipomannan anchor [β-Manp-(1 → 2)-β-Manp]n-(1 → 2)-β-Manp-(1 → 2)-α-Manp-1 → P-(O → 6)-α-Manp-(1 → 2)-Inositol-1-P-(O → 1)-phytoceramide of Candida albicans is reported. The target phospholipomannan (PLM) anchor poses synthetic challenges such as the unusual kinetically controlled (1 → 2)-β-oligomannan domain, anomeric phosphodiester, and unique phytoceramide lipid tail linked to the glycan through a phosphate group. The synthesis of PLM anchor was accomplished using a convergent block synthetic approach using three main appropriately protected building blocks: (1 → 2)-β-tetramannan repeats, pseudodisaccharide, and phytoceramide-1-H-phosphonate. The most challenging (1 → 2)-β-tetramannan domain was synthesized in one pot using the preactivation method. The phytoceramide-1-H-phosphonate was synthesized through an enantioselective A3 three-component coupling reaction. Finally, the phytoceramide-1-H-phosphonate moiety was coupled with pseudodisaccharide followed by deacetylation to produce the acceptor, which on subsequent coupling with tetramannosyl-H-phosphonate provided the fully protected PLM anchor. Final deprotection was successfully achieved by Pearlman's hydrogenation.

Regio/site-selective alkylation of substrates containing a: Cis -, 1,2- or 1,3-diol with ferric chloride and dipivaloylmethane as the catalytic system

In this study, we reported the regio/site-selective alkylation of substrates containing a cis-, 1,2- or 1,3-diol with FeCl3 as a key catalyst. A catalytic system consisting of FeCl3 (0.01-0.1 equiv.) and dipivaloylmethane (FeCl3/dipivaloylmethane = 1/2) was used to catalyze the alkylation in the presence of a base. The produced selectivities and isolated yields were similar to those obtained by methods using the same amount of FeL3 (L = acylacetone ligand) as the catalyst in most cases. The previously reported FeL3 catalysts for alkylation are not commercially available and have to be synthesized prior to use. In contrast, FeCl3 and dipivaloylmethane (Hdipm) are very common and inexpensive nontoxic reagents in the lab, thereby making the method much greener and easier to handle. Mechanism studies confirmed for the first time that FeCl3 initially reacts with two equivalents of Hdipm to form [Fe(dipm)3] in the presence of a base in acetonitrile, followed by the formation of a five or six-membered ring intermediate between [Fe(dipm)3] and two hydroxyl groups of the substrate. A subsequent reaction between the cyclic intermediate and the alkylating agent results in selective alkylation of the substrate.

New sugar donors using the same synthesis of sugar chain

PROBLEM TO BE SOLVED: To provide techniques for efficient chemical synthesis of sugar chains.SOLUTION: There are provided sugar derivatives represented by the formula (Ia) in the figure and methods of synthesizing sugar chains using the same. [In the form

Chemoenzymatic approach for the preparation of asymmetric bi-, tri-, and tetra-antennary N-glycans from a common precursor

Progress in glycoscience is hampered by a lack of well-defined complex oligosaccharide standards that are needed to fabricate the next generation of microarrays, to develop analytical protocols to determine exact structures of isolated glycans, and to elu

An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols

In this study, [Fe(dibm)3] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1,2- and 1,3-diol-containing structures. The mechanism is proposed to proceed via a cyclic dioxolane-type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition-metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation.

The chemoselective O-glycosylation of alcohols in the presence of a phosphate diester and its application to the synthesis of oligomannosylated phosphatidyl inositols

Abstract The glycosylation of hydroxyl groups in the presence of a phosphate diester and its use in the synthesis of oligomannosylated phosphatidiyl inositols are reported. Using a catalytic amount of TMSOTf as an activator for the glycosidation of glycosyl imidates in the presence of a primary alcohol and a phosphate diester provided the desired glycoside along with a glycosyl phosphnate. Complete glycosylation of the primary alcohol required a stoichiometric amount of TMSOTf or TBSOTf. We next examined an application of the method to the synthesis of the phosphatidylinositol mannosides, which are components in the mycobacterial cell wall envelope. Glycosylation of the primary alcohol at the C6 position of a 2,6-dimannosyl myo-inositol core containing a diacylated phosphatidyl lipid with glycosyl imidiates proceeded smoothly to provide multimannosylated inositol derivatives in good yields. However, the 4,6 diol mannoside was a poor acceptor in this reaction.

Cation clock reactions for the determination of relative reaction kinetics in glycosylation reactions: Applications to gluco- and mannopyranosyl sulfoxide and trichloroacetimidate type donors

The development of a cation clock method based on the intramolecular Sakurai reaction for probing the concentration dependence of the nucleophile in glycosylation reactions is described. The method is developed for the sulfoxide and trichloroacetimidate glycosylation protocols. The method reveals that O-glycosylation reactions have stronger concentration dependencies than C-glycosylation reactions consistent with a more associative, SN2-like character. For the 4,6-O-benzylidene-directed mannosylation reaction a significant difference in concentration dependence is found for the formation of the β- and α-anomers, suggesting a difference in mechanism and a rationale for the optimization of selectivity regardless of the type of donor employed. In the mannose series the cyclization reaction employed as clock results in the formation of cis and trans-fused oxabicyclo[4,4,0]decanes as products with the latter being strongly indicative of the involvement of a conformationally mobile transient glycosyl oxocarbenium ion. With identical protecting group arrays cyclization in the glucopyranose series is more rapid than in the mannopyranose manifold. The potential application of related clock reactions in other carbenium ion-based branches of organic synthesis is considered.

Synthesis and conformational analysis of phosphorylated β-(1→2) linked mannosides

Phosphorylated β-(1→2)-oligomannosides are found on the cell surface of several Candida species, including Candida albicans (an opportunistic pathogen). These molecules are believed to take part in the invasion process of fungal infections, which in the case of C. albicans can lead to severe bloodstream infections and death, and can therefore be considered important from a biological standpoint. Understanding the mechanism of their action requires access to the corresponding oligosaccharide model compounds in pure form. In the present work, synthesis of the model core structures involved in the invasion process of C. albicans, consisting of phosphorylated β-(1→2)-linked mannotriose and tetraose, is reported. In order to elucidate the nature of these molecules in more detail, an extensive NMR-spectroscopic study encompassing complete spectral characterization, conformational analysis and molecular modelling was performed. The obtained results were also compared to similar chemical entities devoid of the charged phosphate group.

Regioselective benzylation of diols and polyols by catalytic amounts of an organotin reagent

An efficient one-pot method for the selective benzylation of diols and polyols using 0.1 equiv. of organotin reagents and tetrabutylammonium bromide as catalyst has been developed. The diols and polyols containing a cis-vicinal diol were regioselectively

Cation clock permits distinction between the mechanisms of α- And β-O- and β-C-glycosylation in the mannopyranose series: Evidence for the existence of a mannopyranosyl oxocarbenium ion

The use of a cationic cyclization reaction as a probe of the glycosylation mechanism has been developed and applied to the 4,6-O-benzylidene-protected mannopyranoside system. Cyclization results in the formation of both cis- and trans-fused tricyclic syst