52522-49-3

Basic information

• Product Name: 2,3,5-tri-O-benzyl-1,0-(4-nitrobenzoyl)-D-arabinofuranose
• Synonyms: D-ARABINOFURANOSE, 2,3,5-TRIS-O-(PHENYLMETHYL)-, 4-NITROBENZOATE;2,3,5-TRI-O-BENZYL-1-O-(4-NITROBENZOYL)-D-ARABINOFURANOSE;2,3,5-TRI-O-BENZYL-1-O-(4-NITROBENZOYL)-D-ARABINOFURANOSIDE;2,3,5-TRI-O-BENZYL-1-O-P-NITROBENZOYL-D-ARABINOFURANOSE;2,3,5-tri-o-benzyl-1,0-(4-nitrobenzoyl)-d-arabinofuranose;2,3,5-tri-o-benzyl-d-arabinofuranose 1-(4-nitrobenzoate);2,3,5-TRI-O-BENZYL-D-ARABINOFURANOSE 4-NITROBENZOATE;1-O-NITROBENZOYL-2,3,5-TRI-O-BENZYL-BETA-D-ARABINOFURANOSE
• CAS NO: 52522-49-3
• Molecular Formula: C₃₃H₃₁NO₈
• Molecular Weight: 569.6
• EINECS: 257-992-5
• Mol File: 52522-49-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 86-88 °C(lit.)
• Boiling Point: 633.08°C (rough estimate)
• Flash Point: 246.8 °C
• Appearance: White to Off-white/Powder
• Density: 1.2620 (rough estimate)
• Vapor Pressure: 8.64E-20mmHg at 25°C
• Refractive Index: 1.5960 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• CAS DataBase Reference: 2,3,5-tri-O-benzyl-1,0-(4-nitrobenzoyl)-D-arabinofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-tri-O-benzyl-1,0-(4-nitrobenzoyl)-D-arabinofuranose(52522-49-3)
• EPA Substance Registry System: 2,3,5-tri-O-benzyl-1,0-(4-nitrobenzoyl)-D-arabinofuranose(52522-49-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 52522-49-3(Hazardous Substances Data)

Usage

Chemical Properties

beige powder

InChI:InChI=1/C33H31NO8/c35-32(27-16-18-28(19-17-27)34(36)37)42-33-31(40-22-26-14-8-3-9-15-26)30(39-21-25-12-6-2-7-13-25)29(41-33)23-38-20-24-10-4-1-5-11-24/h1-19,29-31,33H,20-23H2/t29-,30-,31+,33-/m1/s1

Upstream product

• 37776-25-3 2,3,5-tri-O-benzyl-D-arabinose 
• 122-04-3 4-nitro-benzoyl chloride 

Downstream Products

• 863651-22-3 (2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-2,3,4,5-tetrahydro-[2,2']bifuranyl 
• 863651-23-4 (2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-5'-methyl-2,3,4,5-tetrahydro-[2,2']bifuranyl 
• 146-78-1 Fludarabine 
• 143482-59-1 6-azido-2-fluoro-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine 
• 405231-03-0 4-amino-6-fluoro-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazo[4,5-c]pyridine 
• 405231-04-1 4-amino-6-fluoro-1-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)imidazo[4,5-c]pyridine 
• 142372-15-4 2,5,6-Trichloro-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)benzimidazole 
• 78153-61-4 4-Amino-2-methylthio-7-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidin 
• 76081-83-9 4-Amino-7-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidin 
• 5536-17-4 arabinosyl adenine 
• 69275-14-5 ethyl 5-amino-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole-4-carboxylate 
• 64239-99-2 ethyl 5-amino-1-β-D-arabinofuranosylimidazole-4-carboxylate 
• 7013-16-3 9-(β-D-arabinofuranosyl)-9H-purin-6(1H)-one 
• 77856-32-7 1(N)-methyl-9-(2',3',5'-tri-O-benzyl-β-D-arabinofuranosyl)-1(N)-methylisoguanine 

Relevant articles and documents

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.