4060-34-8

Usage

Chemical structure

A complex chemical compound consisting of a D-arabofuranose sugar molecule with chlorination at the 1 position and benzylation at the 2, 3, and 5 positions.

Functional groups

Contains a chloro group (-Cl) at the 1 position and benzyl groups (-CH2Ph) at the 2, 3, and 5 positions.

Stereochemistry

Retains the D-configuration of the arabinose sugar.

Reactivity

The presence of the chloro and benzyl groups makes it a versatile intermediate for the preparation of modified sugars and glycosylation reagents.

Applications

Often used in organic synthesis and medicinal chemistry due to its unique structure and reactivity.

Potential uses

Has potential applications in the development of pharmaceuticals and other biologically active compounds.

Field of interest

Of interest to researchers and scientists working in the field of organic chemistry and drug discovery.

Complexity

Due to its complexity and specific reactivity, it is considered a valuable compound for further research and development.

Upstream product

• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 37776-25-3 2,3,5-tri-O-benzyl-D-arabinose 
• 62255-44-1 1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose 
• 52522-49-3 2,3,5-tri-O-benzyl-1-(4-nitrobenzoyloxy)-D-arabinofuranose 

Downstream Products

• 113574-95-1 1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2-carbonitrile 
• 76054-93-8 5-amino-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole-4-carboxamide 
• 113574-96-2 1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2,4-dicarbonitrile 
• 77856-32-7 1(N)-methyl-9-(2',3',5'-tri-O-benzyl-β-D-arabinofuranosyl)-1(N)-methylisoguanine 
• 110099-70-2 2-ethoxymethyleneamino-5-bromo-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-3,4-dicarbonitrile 
• 119368-24-0 1-((2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4-methoxy-1H-pyrazolo[3,4-b]pyridine 
• 119368-25-1 4-Azido-1-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrazolo[3,4-b]pyridine 
• 119391-49-0 4-(Benzyloxy)-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrazolo<3,4-b>pyridine 
• 139004-10-7 2-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrazolo<3,4-d>pyrimidine-4,6(5H,7H)-dione 
• 139004-08-3 7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrazolo<3,4-d>pyrimidine-4,6(1H,5H)-dione 
• 142544-94-3 4-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrazolo<4,3-d>pyrimidine-5,7(1H,6H)-dione 
• 142544-96-5 1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrazolo<4,3-d>pyrimidine-5,7(4H,6H)-dione 
• 110089-34-4 diethyl 1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-3,4-dicarboxylate 
• 69275-14-5 ethyl 5-amino-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole-4-carboxylate 

Relevant academic research and scientific papers

Straightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals

A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehy

D-arbinose-based synthesis of homo-C-d4T and homo-C-thymidine

2,3,5-Tri-O-benzyl-D-arabinofuranosyl halides (chloride, bromide) were reacted with AllMgBr, MeMgBr, and VinMgBr to furnish anomeric mixtures of the C-glycosyl products. The factors that influenced the β/α ratio are discussed. The α,β-C-vinyl derivative was transformed into 1-deoxy-1-C-hydroxymethyl-β and α-D-arabinofuranoses (2,5-anhydro-D-glucitol and -mannitol, respectively), separable after isopropylidenation step. 2,5-Anhydro-1,3-O-isopropylidene-D-glucitol was converted into 2,5-anhydro-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol and 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine. (Chemical Equation Presented).

Preparation of a fludarabine intermediate via selective alkylation of 2-fluoroadenine

The reaction between 2-fluoroadenine ( 3 ) and 1,3,5-tri- O -benzyl-1- α -d-chloroarabinofuranose ( 4 ) with potassium t- amylate was evaluated in various solvents to afford 9- β -d-(2,3,5-tri- O -benzyl- arabinofuranosyl)-2-fluoroadenine ( 5 ) and the co

Acceptor-dependent stereoselective glycosylation: 2′-CB glycoside-mediated direct β-D-arabinofuranosylation and efficient synthesis of the octaarabinofuranoside in mycobacterial cell wall

(Chemical Equation Presented) A reliable and generally applicable direct method for the stereoselective β-arabinofuranosylation employing a 2′-carboxybenzyl arabinofuranoside as the glycosyl donor has been established. The acyl-protective group on glycosy

Synthesis of oligosaccharide fragments of mannosylated lipoarabinomannan from Mycobacterium tuberculosis

The synthesis of three mannosyl-arabinosides 4-6 found as terminal epitopes of mannosylated lipoarabinomannan (ManLAM) from Mycobacterium tuberculosis is reported. A key step in the synthesis of the required protected octyl β-D-arabinofuranoside derivativ

Purines, Pyrimidines, and Imidazoles. Part 52. New Syntheses of Some 1-β-D-Arabinofuranosylaminoimidazoles and of Related Purine Nucleosides, including 9-β-D-Arabinofuranosyladenine

Ethyl 5-amino-1-β-D-arabinofuranosylimidazole-4-carboxylate and the corresponding carboxamide have been prepared by reaction of ethyl 5-aminoimidazole-4-carboxylate or the carboxamide, respectively with 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride (but not the bromide or iodide) and deblocking.Reaction of the nucleoside ester with formamidine acetate gave 9-β-D-arabinofuranosylhypoxanthine. 5-Amino-4-cyano-1-β-D-arabinofuranosylimidazole obtained by dehydration of the benzylated carboxamide or by direct glycosylation of 5-amino-4-cyanoimidazole and debenzylation of the product, when heated with triethyl orthoformate and ammonia, gave 9-β-D-arabinofuranosyladenine. 2,3,5-Tri-O-benzylarabinofuranosyl chloride with sodium azide, followed by reduction of the glycosyl azide formed with platinic oxide, and condensation of the arabinosylamine produced with ethyl N-(carbamoylcyanomethyl)formimidate gave a mixture of 2,3,5-tri-O-benzyl 1-α- and -β-D-arabinofuranosylimidazole 4-carboxamides.Reduction of the azide with lithium aluminium hydride followed by debenzylation of the product gave, in addition to tho two anomers, 5-amino-1-D-arabinitylimidazole-4-carboxamide.

Imidazo[1,2 c]pyrimidine nucleosides. Synthesis and biological evaluation of certain 1 (β D arabinofuranosyl)imidazo[1,2 c]pyrimidines

The first chemical syntheses of the arabinosylhypoxanthine and arabinosylguanine analogues of the imidazo [1,2 c]pyrimidine series are described. Condensation of trimethylsilyl 7 chloroimidazo[1,2 c]pyrimidin 5 one with 2,3,5 tri O benzyl α D arabinofuranosyl chloride gave 7 chloro 1 (2,3,5 tri O benzyl β D arabinofuranosyl) imidazo[1,2 c]pyrimidin 5 one which on catalytic dehalogenation furnished 1 (2,3,5 tri O benzyl β D arabinofuranosyl)imidazo[1,2 c]pyrimidine 5 one (1). Amination of 3 gave 7 amino 1 (2,3,5 tri O benzyl β D arabinofuranosyl)imidazo [1,2 c]pyrimidin 5 one (2). Reductive hydrogenolysis of 1 and 2 gave 1 (β D arabinofuranosyl)imidazo[1,2 c]pyrimidin 5 one, the arabinosylhypoxanthine analogue, and the corresponding 7 amino isomer, the arabinosylguanine analogue, respectively. The unequivocal assignment of the site of glycosylation and the anomeric configuration have been established. None of the compounds exhibited significant antiviral or antimicrobial activity in vitro.