51450-24-9

Usage

Uses

Used in Organic Synthesis:
HEXA-O-ACETYL-LACTAL is used as a synthetic intermediate for the production of various organic compounds. Its chemical properties make it a valuable building block in the synthesis of complex molecules, contributing to the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
HEXA-O-ACETYL-LACTAL is used as a key component in the development of new drugs. Its unique structure allows for the creation of novel molecular entities with potential therapeutic applications, targeting a wide range of diseases and medical conditions.
Used in Agrochemical Industry:
HEXA-O-ACETYL-LACTAL is utilized as a starting material for the synthesis of new agrochemicals, such as pesticides and herbicides. Its incorporation into these products can lead to improved efficacy, reduced environmental impact, and enhanced selectivity towards target pests.
Used in Specialty Chemicals:
HEXA-O-ACETYL-LACTAL is employed as a raw material in the production of specialty chemicals, which find applications in various industries, including cosmetics, coatings, and materials science. Its versatility in organic synthesis enables the creation of innovative products with unique properties and benefits.

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 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 
• 5160-10-1 2,3,6-tetra-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucopyranosylbromide 
• 70223-97-1 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl bromide 
• 27891-80-1 Acetic acid (2S,3R,4S,5R,6R)-4-acetoxy-6-acetoxymethyl-2-benzenesulfonyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide 
• 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 
• 3616-19-1 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 
• 4753-07-5 α-hepta-O-acetylmaltosyl bromide 
• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 3616-19-1 lactose octaacetate 

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 
• 188426-21-3 1,5-anhydro-3,6-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-D-arabinohex-1-enitol 
• 920968-75-8 4-O-[2,3,4,6-tetra-O-acetyl-(β-D-galactopyranosyl)]-3,6-di-O-acetyl-1,2-dideoxy-1,2-di-(p-toluenesulfonamido)-β-D-glucopyranose 
• 1180510-59-1 penta-O-acetyl-1,5-anhydro-2-deoxy-3-hydroxy-4-O-β-galactopyranosyl-D-arabinohex-1-enitol 
• 65207-55-8 D-lactal 
• 134262-47-8 cyclo<-L-Phenylalanyl-D-prolyl-L-phenylalanyl-L-alanyl-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-O-(3,6-di-O-acetyl-2-desoxy-2-iod-α-D-mannopyranosyl)-(1-6)-L-(2-amino-6-hydroxy)caproyl-L-phenylalanyl-> 

Relevant academic research and scientific papers

Acetobromomaltose, a new source of carbohydrate radicals. EPR characterisation of maltosyl and 2-deoxymaltos-2-yl radicals and syntheses of tetrasaccharide-like mimics, maltal, 3-α-maltosyl propiononitrile, 1,5-anhydromaltitol and 2-deoxymaltopyranoside

The acetoxy-protected maltosyl radical 1, obtained through bromine abstraction from acetobromomaltose (ABM), was studied by means of EPR spectroscopy. At room temperature, only the spectrum of 1 was observed, but at higher temperatures a second radical, t

Iterative synthesis of Leishmania phosphoglycans by solution, solid-phase, and polycondensation approaches without involving any glycosylation

A general strategy (solution, solid-phase, and polycondensation) for the synthesis of antigenic phosphoglycans (PG) of the protozoan parasite Leishmania is presented. Phosphoglycans constitute the variable structural and functional domain of major cell-su

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.

Direct C-H Trifluoromethylation of Glycals by Photoredox Catalysis

A mild, efficient, and practical transformation for the direct C-H trifluoromethylation of glycals under visible light has been reported for the first time. This reaction employed fac-Ir3+(ppy)3 as the photocatalyst, Umemoto's reagent as the CF3 source, and a household blue LED or sunlight as the light source. Glycals bearing both electron-withdrawing and -donating protective groups performed this reaction smoothly. This visible light-mediated trifluoromethylation reaction was highlighted by the trifluoromethylation of the biologically important Neu2en moiety.

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.

A convenient and efficient synthesis of glycals by zinc nanoparticles

A simple and efficient method for the synthesis of pyranoid glycals utilizing the reductive elimination of glycopyranosyl bromides by zinc nanoparticles in an acetate buffer is described. A variety of pyranoid glycals derivatives were obtained, especially for the synthesis of 6-deoxy-4,6-O-benzylidene and disaccharide glycals with good yields.

A facile synthesis of sialylated oligolactosamine glycans from lactose via the Lafont intermediate

The 2-aminophosphonium iodide lactosamine glycoside (Lafont intermediate) readily obtained from lactose has been previously shown not to be amenable to derivatization for oligosaccharide synthesis, but has now been successfully converted via the salicylaldehyde imine into suitably protected lactosamine building blocks (13-16) for glycosylation. The titled strategy has enabled us to rapidly synthesize the Neu5Ac-α-2,3LacNAc-β-1,3LacNAc pentasaccharide and Neu5Ac-α-2,3LacNAc-β-1,3LacNAc-β-1,3LacNAc heptasaccharide. Furthermore, this strategy has been adopted for the synthesis of other 2-amino sugars (e.g., 23-27), which provides a useful method for the preparation of 2-amino sugar building blocks.