138196-19-7

Usage

Uses

Used in Organic Synthesis:
α-D-Galactopyranose1,2-(methylorthoacetate) is used as an intermediate in the synthesis of various organic compounds. Its unique chemical structure allows it to be a versatile building block for the creation of complex molecules with specific properties and applications.
Used in Pharmaceutical Industry:
α-D-Galactopyranose1,2-(methylorthoacetate) is used as a key component in the development of new pharmaceuticals. Its ability to interact with other molecules makes it a promising candidate for the design of drugs targeting specific biological pathways or receptors.
Used in Chemical Research:
a-D-Galactopyranose1,2-(methylorthoacetate) is also utilized in chemical research to study the properties and reactions of sugars and their derivatives. Understanding the behavior of α-D-Galactopyranose1,2-(methylorthoacetate) can contribute to the advancement of knowledge in carbohydrate chemistry and related fields.
Used in Material Science:
The unique properties of α-D-Galactopyranose1,2-(methylorthoacetate) make it a potential candidate for the development of new materials with specific characteristics, such as improved biocompatibility or enhanced mechanical properties.

Upstream product

• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 83-87-4 D-Mannose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 530-26-7 D-Mannose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 60426-93-9 3,4,6-tri-O-acetyl-1,2-O-(1-(exo-p-tolylthio)ethylidene)-alpha-D-glucopyranose 
• 60410-57-3 3,4,6-tri-O-acetyl-1,2-O-(1-(endo-p-tolylthio)ethylidene)-alpha-D-glucopyranose 
• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 50801-29-1 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-α-D-galactopyranose 
• 25878-60-8 D-galactose pentaacetate 

Downstream Products

• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 163523-17-9 6-O-tert-Butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose 
• 324041-25-0 3,4,6-tri-O-benzoyl-1,2-O-[(RS)-1-methoxyethane-1,1-diyl]-β-D-mannopyranose 
• 383367-67-7 (3aS,5R,6R,7S,7aS)-7-Benzyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol 
• 68681-00-5 3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose 
• 852459-74-6 3,4,6-tri-O-benzyl-D-mannono-1,5-lactone 
• 912650-35-2 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulosyl-(2->2)-3,4,6-tri-O-benzyl-D-mannono-1,5-lactone 
• 912650-38-5 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-galacto-hept-2-ulosyl-(2->2)-3,4,6-tri-O-benzyl-D-mannono-1,5-lactone 
• 912650-41-0 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-manno-hept-2-ulosyl-(2->2)-3,4,6-tri-O-benzyl-D-mannono-1,5-lactone 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranoside 
• 20672-66-6 3,4,6-tri-O-benzyl-D-mannopyranose 
• 767340-70-5 1-(3',4',6'-tri-O-benzyl-α-D-mannopyranosyl)prop-2-ene 

Relevant academic research and scientific papers

Chemical Synthesis and Biological Evaluations of Adiponectin Collagenous Domain Glycoforms

The homogeneously glycosylated 76-amino acid adiponectin collagenous domains (ACDs) with all of the possible 15 glycoforms have been chemically and individually synthesized using stereoselective glycan synthesis and chemical peptide ligation. The following biological and pharmacological studies enabled correlating glycan pattern to function in the inhibition of cancer cell growth as well as the regulation of systemic energy metabolism. In particular, hAdn-WM6877 was tested in detail with different mouse models and it exhibited promising in vivo antitumor, insulin sensitizing, and hepatoprotective activities. Our studies demonstrated the possibility of using synthetic glycopeptides as the adiponectin downsized mimetic for the development of novel therapeutics to treat diseases associated with deficient adiponectin.

A Concise Synthesis of Oligosaccharides Derived From Lipoarabinomannan (LAM) with Glycosyl Donors Having a Nonparticipating Group at C2

Mycobacteria infection resulting in tuberculosis (TB) is one of the top ten leading causes of death over the world, and lipoarabinomannan (LAM) has been confirmed to play significant roles in this process. In this study, a convenient synthetic approach ha

β-Mannosylation through O-Alkylation of Anomeric Cesium Alkoxides: Mechanistic Studies and Synthesis of the Hexasaccharide Core of Complex Fucosylated N-Linked Glycans

Several structurally diverse d-mannose-derived lactols, including various deoxy-d-mannoses and conformationally restricted bicyclic d-mannoses, have been synthesized and investigated in mechanistic studies of β-mannosylation through Cs2CO3-mediated anomeric O-alkylation. It was found that deoxy mannoses or conformationally restricted bicyclic d-mannoses are not as reactive as their corresponding parent mannose. This type of β-mannosylation proceeds efficiently when the C2-OH is left free, and protection of that leads to inferior results. NMR studies of d-mannose-derived anomeric cesium alkoxides indicated the predominance of the equatorial β-anomer after deprotonation. Reaction progress kinetic analysis suggested that monomeric cesium alkoxides be the key reactive species for alkylation with electrophiles. DFT calculations supported that oxygen atoms at C2, C3, and C6 of mannose promote the deprotonation of the anomeric hydroxyl group by Cs2CO3 and chelating interactions between Cs and these oxygen atoms favor the formation of equatorial anomeric alkoxides, leading to the highly β-selective anomeric O-alkylation. Based on experimental data and computational results, a revised mechanism for this β-mannosylation is proposed. The utilization of this β-mannosylation was demonstrated by an efficient synthesis of the hexasaccharide core of complex fucosylated N-linked glycans.

Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34

A general and efficient strategy for synthesis of tri-, hexa- and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α-linked galactosamine and the two embedded α-fucose units, which are either branched at positions-3 and -4 or further linked at their 2-position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.

RETRACTED ARTICLE: Chemical synthesis and antigenic activity of a phosphatidylinositol mannoside epitope from: Mycobacterium tuberculosis

Phosphatidylinositol mannosides (PIMs) have been investigated as lipidic antigens for a new subunit tuberculosis vaccine. A non-natural diacylated phosphatidylinositol mannoside (Ac2PIM2) was designed and synthesized by mimicking the natural PIM6 processi

Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

Leishmaniasis, a neglected tropical disease, currently infects approximately 12 million people worldwide with 1 to 2 million new cases each year in predominately underdeveloped countries. The treatment of the disease is severely underdeveloped due to the

Systematic and Stereoselective Total Synthesis of Mannosylerythritol Lipids and Evaluation of Their Antibacterial Activity

The total synthesis of the 20 homogeneous members of mannosylerythritol lipids (MELs) with different alkyl chain lengths was effectively and systematically accomplished from a strategically designed common key intermediate that was stereoselectively constructed by the borinic acid catalyzed β-mannosylation reaction. In addition, their antibacterial activities against Gram-positive bacteria were evaluated. Our results demonstrated that not only the length of the alkyl chains but also the pattern of Ac groups on the mannose moiety were important factors for antibacterial activity.

Concise synthesis and antidiabetic effect of three natural triterpenoid saponins isolated from Fadogia ancylantha (Makoni tea)

The first concise synthesis of the bidesmosidic oleanolic acid saponins 1-3 isolated from Fadogia ancylantha (Makoni tea) have been accomplished through a 'one-pot sequential glycosylation' strategy with two glycosyl 1-(trichloroacetimidate)s as glycosyl donors. The synthesized natural products 1-3 were then evaluated for their inhibitory activities against α-glucosidase, α-amylase, and lipase. Among the assayed compounds 1-3, compound 1 showed strong α-glucosidase and α-amylase inhibition, with IC50 values of 160 and 180 μM, respectively. Moreover, compounds 2 and 3 showed strong inhibition against α-glucosidase and lipase, with the respective IC50 values of 170 and 190 μM, and 190 and 200 μM.

Chemical Synthesis of a Glycopeptide Derived from Skp1 for Probing Protein Specific Glycosylation

Skp1 is a cytoplasmic and nuclear protein, best known as an adaptor of the SCF family of E3-ubiquitin ligases that label proteins for their degradation. Skp1 in Dictyostelium is posttranslationally modified on a specific hydroxyproline (Hyp) residue by a pentasaccharide, which consists of a Fucα1,2-Galβ-1,3-GlcNAcα core, decorated with two α-linked Gal residues. A glycopeptide derived form Skp1 was prepared to characterize the α-galactosyltransferase (AgtA) that mediates the addition of the α-Gal moieties, and to develop antibodies suitable for tracking the trisaccharide isoform of Skp1 in cells. A strategy was developed for the synthesis of the core trisaccharide-Hyp based on the use of 2-naphthylmethyl (Nap) ethers as permanent protecting groups to allow late stage installation of the Hyp moiety. Tuning of glycosyl donor and acceptor reactivities was critical for achieving high yields and anomeric selectivities of glycosylations. The trisaccharide-Hyp moiety was employed for the preparation of the glycopeptide using microwave-assisted solid phase peptide synthesis. Enzyme kinetic studies revealed that trisaccharide-Hyp and trisaccharide-peptide are poorly recognized by AgtA, indicating the importance of context provided by the native Skp1 protein for engagement with the active site. The trisaccharide-peptide was a potent immunogen capable of generating a rabbit antiserum that was highly selective toward the trisaccharide isoform of full-length Skp1. Antibody tracking: A glycopeptide containing a trisaccharide-hydroxyproline moiety was synthesized to characterize the substrate requirements of α-galactosyltransferase (AgtA) that mediates the addition of the α-Gal residues to the glycan of the glycoprotein Skp1 and to develop antibodies suitable for tracking the trisaccharide isoform of Skp1 in cells.

Targeted delivery of fluorescent high-mannose-type oligosaccharide cathepsin inhibitor conjugates

Abstract Three fluorescent cathepsin inhibitor glycoconjugates have been designed, synthesized, and evaluated in terms of their cell internalization and cathepsin inhibitory properties. The conjugates are composed of a peptide epoxysuccinate, capable of c