52443-07-9

Usage

Uses

Used in Organic Chemistry:
2,3,4,6-Tetra-O-acetyl-beta-D-galactopyranosyl cyanide is used as a versatile building block for the synthesis of complex organic molecules, particularly glycosides. Its acetyl groups provide protection for the hydroxyl groups of the sugar moiety, which is essential for the preparation of these biologically significant molecules.
Used in Biological and Medicinal Research:
In the field of biological and medicinal research, 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl cyanide is used as a key intermediate in the synthesis of glycosides. These glycosides are important molecules that play crucial roles in various biological processes and have potential applications in the development of new therapeutic agents.
Used in Chemical Modification and Functionalization:
The presence of the cyanide group in 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl cyanide allows for further chemical modification and functionalization of the compound. This feature makes it a valuable tool in the development of new chemical entities with tailored properties and potential applications in various industries, such as pharmaceuticals, materials science, and agrochemicals.

Upstream product

• 592-04-1 mercury(II) cyanide 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 7677-24-9 trimethylsilyl cyanide 
• 1769-00-2 1,2,3,4,6-penta-O-trimethylsilyl-α-D-galactose 
• 352432-47-4 2,3,4,6-tetra-O-tetramethylsilyl-α-D-galactopyranosyl iodide 
• 10257-28-0 D-Galactose 
• 108-24-7 acetic anhydride 
• 25878-60-8 D-galactose pentaacetate 
• 194546-40-2 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester 
• 68579-18-0 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester 
• 83-87-4 penta-O-acetyl-α-D-galactopyranose 
• 4163-60-4 β-D-galactose peracetate 
• 52443-08-0 3,4,6-tri-O-acetyl-1,2-O-<(exo and endo)-1-cyanoethylidene>-α-D-galactopyranose 
• 83497-42-1 2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-D-galactopyranosyl cyanide 

Downstream Products

• 71420-08-1 1,3-diphenyl-2-(tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptosyl)imidazolidine 
• 228115-83-1 2-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol-1-yl)-1,3-diphenylimidazolidine 
• 352310-78-2 3,4,5,7,-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptose tosylhydrazone 
• 108739-88-4 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonamide 
• 64714-42-7 5-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)tetrazole 
• 108672-06-6 diazomethyl β-D-galactopyranosyl ketone 
• 154706-39-5 2,2-Dimethyl-propionic acid (2S,4aR,5aR,6R,7R,8aR,9S,9aR)-7-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-phenyl-9-[3-(2,2,2-trichloro-acetyl)-ureido]-octahydro-furo[2',3':5,6]pyrano[3,2-d][1,3]dioxin-6-yl ester 
• 154706-33-9 Acetic acid (2S,4aR,6R,7S,8S,8aS)-6-((R)-1-acetoxy-2,2-bis-phenylsulfanyl-ethyl)-2-phenyl-8-trifluoromethanesulfonyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 154706-37-3 2,2-Dimethyl-propionic acid (2S,4aR,5aR,6R,7R,8aR,9S,9aR)-7-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-9-azido-2-phenyl-octahydro-furo[2',3':5,6]pyrano[3,2-d][1,3]dioxin-6-yl ester 
• 154706-31-7 Trifluoro-methanesulfonic acid (2S,4aR,6R,7S,8R,8aS)-6-(2,2-bis-phenylsulfanyl-acetyl)-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 154706-34-0 Acetic acid (2S,4aR,6R,7R,8R,8aR)-6-((R)-1-acetoxy-2,2-bis-phenylsulfanyl-ethyl)-8-azido-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 154706-32-8 Trifluoro-methanesulfonic acid (2S,4aR,6R,7S,8R,8aS)-7-hydroxy-6-((R)-1-hydroxy-2,2-bis-phenylsulfanyl-ethyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 154706-38-4 2,2-Dimethyl-propionic acid (2S,4aR,5aR,6R,7R,8aR,9S,9aR)-7-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-9-amino-2-phenyl-octahydro-furo[2',3':5,6]pyrano[3,2-d][1,3]dioxin-6-yl ester 
• 1053640-25-7 (2S,4aR,6R,7R,8S,8aR)-8-Azido-6-((R)-1-hydroxy-2,2-bis-phenylsulfanyl-ethyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 

Relevant academic research and scientific papers

Improved preparations of some per-O-acetylated aldohexopyranosyl cyanides.

3,4,6-Tri-O-acetyl-1,2-O-[1-(exo-, endo-cyano)ethylidene]-alpha-D- galacto- (1a/b), -alpha-D-gluco- (2a/b), and -beta-D-manno-pyranose (3a/b) were stereoselectively isomerized to the corresponding per-O-acetylated 1,2-trans-aldohexopyranosyl cyanides in 75, 16, and 62% yield, respectively, by treatment with boron trifluoride etherate in dry nitromethane. The corresponding per-O-acetylated 1,2-cis-aldohexopyranosyl cyanides were obtained concurrently in respective yields of 1.9, 0.9, and 4.8%. The per-O-acetylaldohexopyranosyl cyanide products were found stable to the reaction conditions and were readily isolated following completion of the rearrangement. It had previously been proved that reaction of 2,3,4,6-tetra-O-acetyl-alpha-D-manno- and -gluco-pyranosyl bromide with mercuric cyanide in nitromethane generates, in the ratio of approximately 1:1, the desired 1,2-trans-glycosyl cyanides and the corresponding 1,2-O-(1-cyanoethylidene) isomers (3a/b and 2a/b, respectively). Treatment of these reaction-mixtures with boron trifluoride etherate in nitromethane effected the rearrangement of 3a/b and 2a/b, thereby facilitating the isolation, and increasing the overall yields, of the per-O-acetylated 1,2-trans-D-manno- and -gluco-pyranosyl cyanides (58 and 30% total yield, respectively) relative to the earlier procedures. The boron trifluoride etherate-mediated reaction of per-O-acetyl-alpha- and -beta-D-galacto-, -alpha- and -beta-D-gluco-, -alpha-D-manno-, and -2-deoxy-2-phthalimido-beta-D-gluco-pyranoses with trimethylsilyl cyanide in nitromethane was also investigated. This reaction provides a "one-flask" synthesis of the corresponding per-O-acetylated 1,2-trans-aldohexopyranosyl cyanides in which 1,2-O-(1-cyanoethylidene) derivatives are isomerized in situ. Finally, improved preparations of the (not readily accessible) per-O-acetylated 1,2-cis-D-manno- and -gluco-pyranosyl cyanides are described. Thus, 2,3,4,6-tetra-O-acetyl-alpha- and -beta-D-mannopyranosyl cyanide (48 and 16% total yield, respectively) and -alpha- and -beta-D-glucopyranosyl cyanide (12 and 39% total yield, respectively) were synthesized by fusion of the corresponding alpha-D-glycosyl bromides with mercuric cyanide.

Substrate based PET imaging agents

The present application is directed to radiolabeled imaging agents comprising a radiolabel, and a substrate, pharmaceutical compositions comprising radiolabeled imaging agents, and methods of using the radiolabeled imaging agents. The present application is further directed to methods of preparing the radiolabeled imaging agent. Such imaging agents can used in imaging studies, such as Positron Emitting Tomography (PET) or Single Photon Emission Computed Tomography (SPECT).

Synthesis of a protected δ-glyco-amino acid building block for incorporation into peptide chains

The synthesis of a suitably protected sugar amino acid (δ-glyco-amino acid) as a building block to be incorporated into the peptide chain (N-terminus) of bioactive peptide analogues is described. Its efficient coupling reactions with pilot amino acids as

Solid-phase synthesis of cyclic C-glycoside/amino acid hybrids by carbamate coupling chemistry and on-support cyclization

A solid-supported synthesis of cyclic C-glycoside/amino acid conjugates is described. For this purpose, N-(tert-butoxycarbonyl)-[6-O-(p- nitrophenoxycarbonyl)-2,3,4-tri-O-(p-toluoyl)-β-D-glycopyranosyl] methylamines derived from galactose and glucose were

(-)-Daucic acid: Proof of D-lyxo configuration, synthesis of its D-ribo, D-xylo, L-arabino and L-lyxo analogs, and biosynthetic implications

The dimethyl esters of the 2,6-anhydro-3-deoxy-hept-2-enaric acids with D-xylo, D-lyxo, L-arabino, L-lyxo- and D-ribo-configuration were synthesized from D-galactose and D-mannose, respectively, and further characterized by their di-O-acetyl and di-O-benz

(-)-Daucic Acid: Revision of Configuration, Synthesis, and Biosynthetic Implications

The synthesis of dihydropyrans with the D-xylo (1), D-ribo, L-arabino, and D-lyxo (2) configuration by one-carbon-atom homologation of D-mannose or D-galactose, terminal oxidation, and directed β elimination revealed (-)-daucic acid isolated from carrots

Efficient stereocontrolled synthesis of C-glycosides using glycosyl donors substituted by propane 1,3-diyl phosphate as the leaving group

α- and β-Glycosyl cyanides, per-O-acetyl-1,2-O-1-cyanoethylidenes and C-allyl glycopyranosides were efficiently prepared by treatment of 2,3,4-tri-O-acetyl-α,β-L-rhamno-, L-fuco- and 2,3,4,6-tetra-O-acetyl-α,β-D-galactopyranosyl propane-1,3-diyl phosphate

Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-O-silylated Mono- and Disaccharides

Reported herein is a general method for the efficient syntheses of a variety of β-cyano glycosides through the activation of per-O-trimethylsilyl glycosides with TMSI to form α-glycosyl iodides, which undergo SN2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)6 in THF/H2O to give the corresponding aminomethyl glycosides.

The cyanation reaction of O-acetylated S-glycosyl phosphorothioates.

The reaction of alpha- and beta-1-S-phosphorothioates of per-O-acetylated monosaccharides (galactose, xylose, glucose) with trimethylsilyl cyanide in the presence of boron trifluoride etherate has been investigated. It has been established that in dichlor

Behaviour of the primary nitro group under denitration conditions

Treatment of per-O-acetylated or acetalated glycosylnitromethanes derived from the common hexoses and pentoses with tributyltin hydride and a catalytic amount of a radical initiator [1,1′-azobis(cyclohexanecarbonitrile)] in refluxing benzene easily afforded the corresponding glycosylmethanal oximes in 84-97% yields. Per-O-acetylated C-β-glycopyranosylmethanal oximes were employed for synthesis of versatile C-β-glycopyranosyl cyanides of the β-D-gluco, β-D-manno, β-D-galacto, β-D-xylo, and β-L-rhamno configurations.