67314-34-5

Usage

Uses

Used in Organic Synthesis:
Hexa-O-acetylmaltal is used as a key intermediate in the synthesis of various complex carbohydrates and their derivatives. Its acetylated structure allows for selective deprotection and functionalization, making it a versatile building block for the preparation of diverse carbohydrate structures.
Used in Copper-Mediated Glycosylations:
In the field of carbohydrate chemistry, Hexa-O-acetylmaltal is specifically used as a glycosyl donor in copper-mediated glycosylations. This application takes advantage of its reactivity and stability, enabling the formation of glycosidic bonds under mild conditions. This method is particularly useful for the synthesis of oligosaccharides and glycoconjugates, which are important in biological systems and have potential applications in pharmaceuticals, diagnostics, and materials science.
Used in Pharmaceutical Industry:
Hexa-O-acetylmaltal plays a crucial role in the development of glycoconjugate drugs, which are compounds that consist of a carbohydrate moiety covalently linked to a non-carbohydrate molecule, such as a protein or lipid. These glycoconjugates have various applications in the pharmaceutical industry, including vaccines, therapeutic antibodies, and drug delivery systems. The use of Hexa-O-acetylmaltal in the synthesis of these glycoconjugates can improve their stability, efficacy, and targeted delivery.
Used in Materials Science:
In materials science, Hexa-O-acetylmaltal can be utilized in the development of carbohydrate-based materials, such as hydrogels, films, and nanoparticles. These materials have potential applications in areas like drug delivery, tissue engineering, and biosensing. The use of Hexa-O-acetylmaltal in the synthesis of these materials can provide enhanced properties, such as improved biocompatibility, stimuli-responsiveness, and functionalization capabilities.

InChI:InChI=1/C24H32O15/c1-11(25)32-9-18-20(17(7-8-31-18)34-13(3)27)39-24-23(37-16(6)30)22(36-15(5)29)21(35-14(4)28)19(38-24)10-33-12(2)26/h7-8,17-24H,9-10H2,1-6H3/t17-,18-,19-,20+,21-,22+,23-,24-/m1/s1

Upstream product

• 4753-07-5 α-hepta-O-acetylmaltosyl bromide 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 
• 3616-19-1 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 
• 6920-00-9 D-maltose octaacetate 
• 22352-19-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate 

Downstream Products

• 239806-28-1 4-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->5)-(7-O-acetyl-2,6-anhydro-1,3,4-trideoxy-α,β-D-erythro-hept-3-enitol-1-yl)]iodobenzene 
• 1381863-35-9 C₅₇H₆₃NO₂₄S 
• 1381863-33-7 C₅₇H₆₉NO₂₁S 
• 1381863-34-8 C₅₇H₆₉NO₂₁S 
• 1381863-31-5 C₃₉H₅₇NO₁₆S 
• 1381863-32-6 C₃₉H₅₃NO₁₆S 
• 1381863-29-1 C₃₂H₄₃NO₁₆S 
• 1381863-28-0 C₃₆H₄₅NO₁₆S 

Relevant academic research and scientific papers

Synthesis of C-Oligosaccharides through Versatile C(sp3)?H Glycosylation of Glycosides

C-oligosaccharides are pharmacologically relevant because they are more hydrolysis-resistant than O-oligosaccharides. Despite indisputable advances, C-oligosaccharides continue to be underdeveloped, likely due to a lack of efficient and selective strategies for the assembly of the interglycosidic C?C linkages. In contrast, we, herein, report a versatile and robust strategy for the synthesis of structurally complex C-oligosaccharides via catalyzed C(sp3)?H activations. Thus, a wealth of complex interglycosidic (2→1)- and (1→1)-C-oligosaccharides becomes readily available by palladium-catalyzed C(sp3)?H glycoside glycosylation. The isolation of key palladacycle intermediates and experiments with isotopically-labeled compounds identified a trans-stereoselectivity for the C(sp3)?H glycosylation. The glycoside C(sp3)?H activation manifold was likewise exploited for the diversification of furanoses, pyranoses and disaccharides.

2-nitroglycal and efficient synthesis method thereof

The invention discloses an efficient synthesis method of 2-nitroglycal, and belongs to the technical field of synthesis of sugar. The structure of the 2-nitroglycal is shown in the specification. Secondly, the invention also provides a preparation method of the 2-nitro saccharide alkene, and the preparation method provided by the invention can be used for efficiently preparing the 2-nitroglycal through one-step synthesis.

From 1,4-Disaccharide to 1,3-Glycosyl Carbasugar: Synthesis of a Bespoke Inhibitor of Family GH99 Endo-α-mannosidase

Understanding the enzyme reaction mechanism can lead to the design of enzyme inhibitors. A Claisen rearrangement was used to allow conversion of an α-1,4-disaccharide into an α-1,3-linked glycosyl carbasugar to target the endo-α-mannosidase from the GH99 glycosidase family, which, unusually, is believed to act through a 1,2-anhydrosugar "epoxide" intermediate. Using NMR and X-ray crystallography, it is shown that glucosyl carbasugar α-aziridines can act as reasonably potent endo-α-mannosidase inhibitors, likely by virtue of their shape mimicry and the interactions of the aziridine nitrogen with the conserved catalytic acid/base of the enzyme active site.

Synthesis of 2-deoxy-2,2-difluoro-α-maltosyl fluoride and its X-ray structure in complex with Streptomyces coelicolor GlgEI-V279S

Streptomyces coelicolor (Sco) GlgEI is a glycoside hydrolase involved in α-glucan biosynthesis and can be used as a model enzyme for structure-based inhibitor design targeting Mycobacterium tuberculosis (Mtb) GlgE. The latter is a genetically validated drug target for the development of anti-Tuberculosis (TB) treatments. Inhibition of Mtb GlgE results in a lethal buildup of the GlgE substrate maltose-1-phosphate (M1P). However, Mtb GlgE is difficult to crystallize and affords lower resolution X-ray structures. Sco GlgEI-V279S on the other hand crystallizes readily, produces high resolution X-ray data, and has active site topology identical to Mtb GlgE. We report the X-ray structure of Sco GlgEI-V279S in complex with 2-deoxy-2,2-difluoro-α-maltosyl fluoride (α-MTF, 5) at 2.3 ? resolution. α-MTF was designed as a non-hydrolysable mimic of M1P to probe the active site of GlgE1 prior to covalent bond formation without disruption of catalytic residues. The α-MTF complex revealed hydrogen bonding between Glu423 and the C1F which provides evidence that Glu423 functions as proton donor during catalysis. Further, hydrogen bonding between Arg392 and the axial C2 difluoromethylene moiety of α-MTF was observed suggesting that the C2 position tolerates substitution with hydrogen bond acceptors. The key step in the synthesis of α-MDF was transformation of peracetylated 2-fluoro-maltal 1 into peracetylated 2,2-difluoro-α-maltosyl fluoride 2 in a single step via the use of Selectfluor.

Synthesis of 2-deoxy-2,2-difluoro-α-maltosyl fluoride and its X-ray structure in complex with Streptomyces coelicolor GlgEI-V279S

Streptomyces coelicolor (Sco) GlgEI is a glycoside hydrolase involved in α-glucan biosynthesis and can be used as a model enzyme for structure-based inhibitor design targeting Mycobacterium tuberculosis (Mtb) GlgE. The latter is a genetically validated drug target for the development of anti-Tuberculosis (TB) treatments. Inhibition of Mtb GlgE results in a lethal buildup of the GlgE substrate maltose-1-phosphate (M1P). However, Mtb GlgE is difficult to crystallize and affords lower resolution X-ray structures. Sco GlgEI-V279S on the other hand crystallizes readily, produces high resolution X-ray data, and has active site topology identical to Mtb GlgE. We report the X-ray structure of Sco GlgEI-V279S in complex with 2-deoxy-2,2-difluoro-α-maltosyl fluoride (α-MTF, 5) at 2.3 ? resolution. α-MTF was designed as a non-hydrolysable mimic of M1P to probe the active site of GlgE1 prior to covalent bond formation without disruption of catalytic residues. The α-MTF complex revealed hydrogen bonding between Glu423 and the C1F which provides evidence that Glu423 functions as proton donor during catalysis. Further, hydrogen bonding between Arg392 and the axial C2 difluoromethylene moiety of α-MTF was observed suggesting that the C2 position tolerates substitution with hydrogen bond acceptors. The key step in the synthesis of α-MDF was transformation of peracetylated 2-fluoro-maltal 1 into peracetylated 2,2-difluoro-α-maltosyl fluoride 2 in a single step via the use of Selectfluor.

Synthesis of fluorinated maltose derivatives for monitoring protein interaction by 19F NMR

A novel reporter system, which is applicable to the 19F NMR investigation of protein interactions, is presented. This approach uses 2-F-labeled maltose as a spy ligand to indirectly probe protein-ligand or protein-protein interactions of proteins fused or tagged to the maltose-binding protein (MBP). The key feature is the simultaneous NMR observation of both 19F NMR signals of gluco/ manno-type-2-F-maltose-isomers; one isomer (α-gluco-type) binds to MBP and senses the protein interaction, and the nonbinding isomers (β-gluco- and/or α/β-manno-type) are utilized as internal references. Moreover, this reporter system was used for relative affinity studies of fluorinated and nonfluorinated carbohydrates to the maltose-binding protein, which were found to be in perfect agreement with published X-ray data. The results of the NMR competition experiments together with the established correlation between 19F chemical shift data and molecular interaction patterns, suggest valuable applications for studies of protein-ligand interaction interfaces.

A rapid synthesis of pyranoid glycals promoted by β-cyclodextrin and ultrasound

A convenient and environmentally benign procedure for the synthesis of glycals from glycosyl bromides with very low zinc dust loading (1.5 equiv.) is described. The process is activated by β-cyclodextrin and ultrasound. Based on 19 samples, this method has been demonstrated to be highly effective for a broad range of glycosyl bromides, including acid- or base-sensitive and disaccharide glycosyl bromides. A yield of 85%-96% of glycals was obtained. Copyright

A mild and environmentally benign method for the synthesis of glycals in PEG-600/H2O

Glycals were synthesized via a simple, mild, convenient and environmentally benign procedure, in which protected glycosyl bromides undergo the reductive elimination in the presence of zinc in PEG-600/H2O at room temperature. The glycals were obtained in 75-92% isolated yields.

Versatile and mild synthesis of Di- and trisaccharidic 2-enopyranosyl cyanides by cyanation of per-O-acetylglycals with trimethylsilyl cyanide catalyzed by palladium(II) acetate

A catalytic amount (1-2 mol%) of palladium(II) acetate was found to work as a catalyst for the cyanation of di- and trisaccharidic per-O-acetylglycals with trimethylsilyl cyanide to afford di- and trisaccharidic 2-enopyranosyl cyanides in high yields and in moderate stereoselectivities. Georg Thieme Verlag Stuttgart.

Mild synthesis of disaccharidic 2,3-enopyranosyl cyanides and 2-C-2-deoxy pyranosyl cyanides with Hg(CN)2/HgBr2/TMSCN

Lewis acid-catalyzed dimerization of mono- and disaccharidic per-O-acetylated glycals gave di- and tetrasaccharidic O-acetylated C-glycosides, respectively. 2,3-Enopyranosyl cyanides were obtained from per-O-acetylated glycals by a new, mild anomeric SN′-acetoxy displacement with Hg(CN)2/HgBr2/TMSCN. Per-O-acetylated 2-C-2-deoxy-pyranoses were converted into pyranosyl cyanides by the same reagent. An unprecedented acetic acid elimination from dimers with D-galacto- and L-fuco-configurations accompanied the SN-displacement under those conditions. A new set of 1H NMR coupling constants for 2,3-enopyranosyl systems was used for configurational assignment of complicated tetrasaccharide mimics.