86520-63-0

Usage

Uses

Used in Organic Synthesis:
.alpha.-D-Galactopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate) is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure allows for selective reactions and modifications, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Carbohydrate Chemistry:
In the field of carbohydrate chemistry, .alpha.-D-Galactopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate) serves as a versatile reagent for the synthesis of oligosaccharides, glycoconjugates, and other carbohydrate-based compounds. Its acetylated and trichloroethanimidate functionalities facilitate efficient glycosylation reactions, enabling the formation of complex carbohydrate structures with high selectivity and yield.
Used in Drug Development:
.alpha.-D-Galactopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate) is also utilized in drug development as a potential pharmaceutical agent or as a precursor for the synthesis of bioactive molecules. Its unique structure and reactivity make it a promising candidate for the development of new drugs targeting various diseases and conditions.
Used in Material Science:
In material science, .alpha.-D-Galactopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate) can be employed in the design and synthesis of novel materials with specific properties, such as stimuli-responsive hydrogels, self-assembling systems, and functional coatings. Its ability to form stable glycosidic linkages and its compatibility with various polymers and materials make it a valuable component in the development of advanced materials for various applications.

InChI:InChI=1/C16H20Cl3NO10/c1-6(21)25-5-10-11(26-7(2)22)12(27-8(3)23)13(28-9(4)24)14(29-10)30-15(20)16(17,18)19/h10-14,20H,5H2,1-4H3/t10-,11-,12-,13-,14+/m0/s1

Upstream product

• 545-06-2 trichloroacetonitrile 
• 4163-60-4 β-D-galactose peracetate 
• 25878-60-8 D-galactose pentaacetate 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 100-46-9 benzylamine 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 630-18-2 tert-butyl isocyanide 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 492-61-5 β-D-glucose 
• 50-99-7 D-glucose 
• 83-87-4 D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 

Downstream Products

• 2530-07-6 tigogenyl acetate 
• 28154-24-7 O-β-tigogenyl glucoside tetraacetate 
• 159419-17-7 but-3-enyl 2,4,6-tri-O-benzyl-3-O-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucoside 
• 13035-51-3 tert-butyl-(tetra-O-acetyl-β-D-glucopyranoside) 
• 1192262-84-2 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-4-phenylethynyl-α-D-galactopyranoside 
• 1192262-89-7 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-4-trimethylsilylethynyl-α-D-galactopyranoside 
• 72500-10-8 methyl 3-methoxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetoxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoate 
• 119643-01-5 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(2,6-dimethoxy-4-(methoxycarbonyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1186009-42-6 C₄₈H₅₄O₁₆ 
• 67909-25-5 4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 18997-57-4 4-methylumbelliferyl β-D-glucopyranoside 
• 1352299-63-8 (3R,4S,6R)-2-(acetoxymethyl)-6-(3-(5-(2-(benzyloxy)-2-oxoethyl)-3-tert-butyl-2,4-dioxoimidazolidin-1-yl)propoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1352299-67-2 (3R,4S,6R)-2-(acetoxymethyl)-6-(3-(5-(2-((S)-1-(benzyloxy)-4-methyl-1-oxopentan-2-ylamino)-2-oxoethyl)-3-tert-butyl-2,4-dioxoimidazolidin-1-yl)propoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 84812-00-0 3,4-dimethoxybenzyl alcohol O-β-D-glucopyranoside 

Relevant academic research and scientific papers

PROCESS OF SYNTHESIS OF β-6'SULFOQUINOVOSYL DIACYLGLYCEROLS

The present invention relates to a synthesis process of β-6-sulfoquinovosyl-diacylglycerols. In particular, said process is for the synthesis of the compounds 1,2-O-distearoyl-3-O-(β- sulfoquinovosyl)-R/S-glycerol, 1,2-O-distearoyl-3-O-(β-sulfoquinovosyl)-R-glycerol or 1,2- O-distearoyl-3-O-(β-sulfoquinovosyl)-S-glycerol, named respectively Sulfavant A, Sulfavant R and Sulfavant S.

Synthesis of malformin-A1, C, a glycan, and an aglycon analog: Potential scaffolds for targeted cancer therapy

Improvement in therapeutic efficacy while reducing chemotherapeutic side effects remains a vital objective in synthetic design for cancer treatment. In keeping with the ethos of therapeutic development and inspired by the Warburg effect for augmenting biological activities of the malformin family of cyclic-peptide natural products, specifically anti-tumor activity, a β-glucoside of malformin C has been designed and synthesized utilizing precise glycosylation and solution phase peptide synthesis. We optimized several glycosylation procedures utilizing different donors and acceptors. The overarching goal of this study was to ensure a targeted delivery of a glyco-malformin C analog through the coupling of D-glucose moiety; selective transport via glucose transporters (GLUTs) into tumor cells, followed by hydrolysis in the tumor microenvironment releasing the active malformin C a glycon analog. Furthermore, total synthesis of malformin C was carried out with overall improved strategies avoiding unwanted side reactions thus increasing easier purification. We also report on an improved solid phase peptide synthesis protocol for malformin A1.

Blockwise synthesis of polylactosamine fragments and keratan sulfate oligosaccharides comprised of dimeric Galβ(1 → 4)GlcNAc6Sβ

In this paper, the chemical synthesis of polylactosamine fragments up to docosasaccharide (22-mer) via the blockwise synthetic approach is reported. We used suitably protected tetrasaccharide and octasaccharide sequences as key building blocks. The use of such large building blocks as glycosyl donors and acceptors enabled the rapid construction of polysaccharide frameworks. Furthermore, the coupling reaction between these large building blocks facilitated the purification of glycosylated products, for which size exclusion column chromatography is highly effective. Then, we applied the building blocks to the synthesis of keratan sulfate glycan, which is partially sulfated poly-N-acetyllactosamine. Consequently, we achieved the synthesis of the octasaccharide of a keratan sulfate glycan comprised of a repeating Galβ(1 → 4)GlcNAc6Sβ disaccharide unit.

Nitrogen-containing aromatic ring derivative containing galactose and application thereof

The invention belongs to the technical field of medicines, and relates to a nitrogen-containing aromatic ring derivative containing galactose, application thereof and a pharmaceutical composition containing the compound. The invention also relates to a method for preparing the compound and the pharmaceutical composition, and application of the compound and the pharmaceutical composition in prevention or treatment of tumors, inflammatory diseases, autoimmune diseases and other diseases, especially tumors.

An alternative approach for the synthesis of sulfoquinovosyldiacylglycerol

Sulfoquinovosyldiacylglycerol (SQDG) is a glycolipid ubiquitously found in photosyn-thetically active organisms. It has attracted much attention in recent years due to its biological ac-tivities. Similarly, the increasing demand for vegan and functional foods has led to a growing interest in micronutrients such as sulfolipids and their physiological influence on human health. To study this influence, reference materials are needed for developing new analytical methods and providing enough material for model studies on the biological activity. However, the availability of these materials is limited by the difficulty to isolate and purify sulfolipids from natural sources and the unavailability of chemical standards on the market. Consequently, an alternative synthetic route for the comprehensive preparation of sulfolipids was established. Here, the synthesis of a sulfolipid with two identical saturated fatty acids is described exemplarily. The method opens possibilities for the preparation of a diverse range of interesting derivatives with different saturated and unsatu-rated fatty acids.

3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL

The present invention relates to a 3'-ketoglycoside compound defined by formula (I) and its use for controlled release of alcohols, in particular alcohols showing an insect repellent effect. It relates also to a process for preparing the 3'-ketoglycoside compound of formula (I). It further relates to a composition comprising a 3'- ketoglycoside compound of formula (I). It relates also to the use of a 3'-ketoglycoside compound of formula (I) for the controlled release of alcohols. It related also to a method of use of such composition.

Revealing Functional Significance of Interleukin-2 Glycoproteoforms Enabled by Expressed Serine Ligation

Naturally occurring interleukin-2 (IL-2) is a pleiotropic glycoprotein that regulates immune responses by controlling the differentiation and homeostasis of T cells. Non-glycosylated IL-2 has been used in clinical settings for three decades. However, the function of the O-glycan of native IL-2 remains elusive. Herein, to stress this issue, we report a highly efficient semi-synthesis of homogeneous glycosylated IL-2 with various glycoproteoforms on a multi-milligram scale. The glycopeptide fragment was prepared by chemical synthesis and then merged with recombinant fragment via a serine ligation to generate the desired glycoprotein in a single operation. Biological evaluation of the homogenous glycoprotein library reveals that the activity of IL-2 in activating individual T cell subset is glycan dependent, thus highlighting the possibility of further improving current clinical medicine.

Nanoparticles to Study Lectins in Caenorhabditis elegans: Multivalent Galactose β1-4 Fucose-Functionalized Dendrimers Provide Protection from Oxidative Stress

Galectins are galactoside-binding lectins that are functional dimers or higher-order oligomers. Multivalent binding has been shown to augment the relatively low affinity of the galectins for their galactoside-binding partners, enabling the galectins to pl

Synthesis of Asparagine Derivatives Harboring a Lewis X Type DC-SIGN Ligand and Evaluation of their Impact on Immunomodulation in Multiple Sclerosis

The protein myelin oligodendrocyte glycoprotein (MOG) is a key component of myelin and an autoantigen in the disease multiple sclerosis (MS). Post-translational N-glycosylation of Asn31 of MOG seems to play a key role in modulating the immune response towards myelin. This is mediated by the interaction of Lewis-type glycan structures in the N-glycan of MOG with the DC-SIGN receptor on dendritic cells (DCs). Here, we report the synthesis of an unnatural Lewis X (LeX)-containing Fmoc-SPPS-compatible asparagine building block (SPPS=solid-phase peptide synthesis), as well as asparagine building blocks containing two LeX-derived oligosaccharides: LacNAc and Fucα1-3GlcNAc. These building blocks were used for the glycosylation of the immunodominant portion of MOG (MOG31-55) and analyzed with respect to their ability to bind to DC-SIGN in different biological setups, as well as their ability to inhibit the citrullination-induced aggregation of MOG31-55. Finally, a cytokine secretion assay was carried out on human monocyte-derived DCs, which showed the ability of the neoglycopeptide decorated with a single LeX to alter the balance of pro- and anti-inflammatory cytokines, inducing a tolerogenic response.