176299-96-0

Usage

Uses

Used in Organic Chemistry:
4-Methoxyphenyl 4,6-O-Benzylidene-beta-D-galactopyranoside is used as a reagent in the synthesis of carbohydrate-based molecules, facilitating the creation of complex organic structures and contributing to the development of novel compounds with potential applications in various fields.
Used in Biochemistry:
In the field of biochemistry, 4-Methoxyphenyl 4,6-O-Benzylidene-beta-D-galactopyranoside serves as a reagent in glycosylation reactions, which are crucial for the formation of glycoproteins and other biomolecules. Its use in these reactions aids in the study and development of biologically active compounds.
Used in Pharmaceutical Research:
4-Methoxyphenyl 4,6-O-Benzylidene-beta-D-galactopyranoside is used as a starting material in the development of pharmaceuticals, particularly for the synthesis of glycosidic linkages in drug candidates. Its structural modifications may enhance biological activity and pharmacological properties, making it a valuable tool in drug discovery and design.
Used in Material Science:
In material science, 4-Methoxyphenyl 4,6-O-Benzylidene-beta-D-galactopyranoside may be utilized in the development of carbohydrate-based materials, such as polymers and coatings, due to its unique structural features and potential for modification. This can lead to the creation of new materials with specific properties for various applications.

InChI:InChI=1/C20H22O7/c1-23-13-7-9-14(10-8-13)25-20-17(22)16(21)18-15(26-20)11-24-19(27-18)12-5-3-2-4-6-12/h2-10,15-22H,11H2,1H3/t15-,16+,17-,18-,19?,20+/m0/s1

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 3150-20-7 4-methoxyphenyl β-D-galactopyranoside 
• 2872-65-3 4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 10257-28-0 D-Galactose 
• 150-76-5 4-methoxy-phenol 
• 2872-65-3 p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 61403-03-0 per-acetyl-β-D-galactose 
• 25878-60-8 D-galactose pentaacetate 
• 3150-20-7 4-methoxyphenyl β-D-glucopyranoside 

Downstream Products

• 671194-39-1 4-methoxyphenyl 3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 1001847-14-8 p-methoxyphenyl 4,6-O-benzylidene-3-O-tris(isopropyl)silyl-β-D-galactopyranoside 
• 1138123-83-7 C₄₂H₄₄Cl₃NO₁₈ 
• 1138125-17-3 C₄₂H₄₆Cl₃NO₁₈ 
• 1138125-22-0 C₄₃H₄₅Cl₃F₃NO₂₀S 
• 1138124-43-2 C₄₄H₄₈Cl₃NO₁₉ 
• 1426099-69-5 C₃₁H₃₈Cl₃N₃O₁₈ 
• 1138124-35-2 C₄₄H₄₈Cl₃NO₁₉ 
• 1426099-71-9 C₃₇H₄₂Cl₃NO₁₉ 
• 1426099-72-0 C₃₇H₄₀Cl₃NO₂₀ 
• 1426099-74-2 C₃₇H₄₁Cl₃N₂O₁₉ 
• 1426099-68-4 C₂₇H₂₆O₉ 
• 869107-36-8 4-methoxyphenyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Convergent Synthesis of Digalactosyl Diacylglycerols

Efficient convergent chemical syntheses of digalactosyl diacylglycerols (DGDGs), which have both a galactose-galactose α(1→6)-linkage and a galactose-glycerol β-linkage along with a diacylglycerol containing various kinds of fatty acids, have been accomplished. In order to achieve a concise synthesis, we chose to use allylic protective groups as permanent protective groups. We have also achieved α- and β-selective glycosylations for the respective linkages with high yields as the key steps.

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.

Studies towards the total synthesis of repeating unit of O-sulfated polysaccharide from marine bacterium Cobetia pacifica KMM 3878

Herein we report assembly of the appropriately protected trisaccharide repeating unit of Cobetia pacifica KMM 3878 O-sulfated polysaccharide. Our synthesis involves 3,4-O-pyruvilated galactose as the key building block which acts as a donor as well as acceptor in the construction of trisaccharide. We obtained the R isomer as a major stereoisomer in the pyruvilation reaction. The glycosylations proceeded with high stereo and regioselectivity.

HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS WITH ALTERED GLYCOSYL GROUPS

Glycosphingolipids (GSLs) bearing α-glucose (α-Glc) that preferentially stimulate human invariant NKT (iNKT) cells are provided. GSLs with α-glucose (α-Glc) that exhibit stronger induction in humans (but weaker in mice) of cytokines and chemokines and exp

Tuning the moenomycin pharmacophore to enable discovery of bacterial cell wall synthesis inhibitors

New antibiotic drugs need to be identified to address rapidly developing resistance of bacterial pathogens to common antibiotics. The natural antibiotic moenomycin A is the prototype for compounds that bind to bacterial peptidoglycan glycosyltransferases

A divergent approach to the synthesis of simplexides and congeners via a late-stage olefin cross-metathesis reaction

Simplexides constitute a unique group of immunosuppressive glycolipids that demonstrate antiproliferative activities against activated T-cell lymphocytes via a unique non-cytotoxic inhibition. To investigate the structure-activity relationship of the varied long-chain secondary alcohols on simplexides, we developed an efficient and divergent route to the synthesis of simplexides and congeners, taking advantage of a late-stage olefin cross-metathesis reaction.

Synthesis of a tetrasaccharide related to the triterpenoid saponin isolated from Schima noronhae

A concise synthesis of a tetrasaccharide related to the cell-growth inhibitory triterpenoid saponin isolated from Schima noronhae is reported. A late stage 2,2,6,6-tetramethylpiperidinyloxy (TEMPO)-mediated oxidation of a primary hydroxyl group to carboxylic acid has been achieved under phase-transfer conditions. Stereoselective glycosylations were carried out using thioglycoside or glycosyl trichloroacetimidate activation using sulfuric acid immobilized on silica (H2SO4-silica) in conjunction with N-iodosuccinimide and alone, respectively.

Efficient iodine-catalyzed preparation of benzylidene acetals of carbohydrate derivatives

An efficient preparation of benzylidene acetals of carbohydrate derivatives catalyzed by iodine has been developed. Yields were excellent in every case. Copyright Taylor & Francis Group, LLC.

Stereocontrolled and convergent entry to CF2-sialosides: Synthesis of CF2-linked ganglioside GM4

Sialidase-resistant ganglioside analogues having biological activities similar to those of natural gangliosides are expected to be important probes for clarifying the biological functions of gangliosides. Focusing on difluoromethylene-linked (CF2-linked) α(2,3)sialylgalactose as a core structure of sialidase-resistant ganglioside mimics, we have developed novel, stereocontrolled, and efficient methodologies to synthesize CF2-sialosides based on Ireland-Claisen rearrangement. CF2-linked α(2,3)sialylgalactose and CF2-linked GM4 were synthesized. Copyright

Galabiosyl donors; efficient synthesis from 1,2,3,4,6-penta-O-acetyl-β-D-galactopyranose

1,2,3,4,6-Penta-O-acetyl-β-D-galactopyranose was transformed into phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (5) and 4-methoxyphenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside (8) in 73% (two steps) and 58% (three steps) yield, respectively. Glycosylation of the acceptor 8 with donor 5 using N-iodosuccinimide-trimethylsilyl trifluoromethanesulfonate as promoter furnished the galabioside 9 (8.8 g) in 95% yield. Further transformations provided in high yields anomerically-activated galabiosides (thioglycoside (1), trichloroacetimidate (2), and bromosugar (3)) suitable for use as glycosyl donors in syntheses of galabiose-containing oligosaccharides. Several of the compounds reported here are crystalline, which greatly simplified purifications. (C) 2000 Elsevier Science Ltd.