23624-64-8

Basic information

• Product Name: 4-(benzoylamino)-1-(2,3,5-tri-O-benzoylpentofuranosyl)pyrimidin-2(1H)-one
• CAS NO: 23624-64-8
• Molecular Formula: C₃₇H₂₉N₃O₉
• Molecular Weight: 659.6409
• Mol File: 23624-64-8.mol

Chemical Properties

• Density: 1.35g/cm³
• Refractive Index: 1.648
• CAS DataBase Reference: 4-(benzoylamino)-1-(2,3,5-tri-O-benzoylpentofuranosyl)pyrimidin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(benzoylamino)-1-(2,3,5-tri-O-benzoylpentofuranosyl)pyrimidin-2(1H)-one(23624-64-8)
• EPA Substance Registry System: 4-(benzoylamino)-1-(2,3,5-tri-O-benzoylpentofuranosyl)pyrimidin-2(1H)-one(23624-64-8)

Safety Data

• Hazardous Substances Data: 23624-64-8(Hazardous Substances Data)

Upstream product

• 85743-99-3 N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide 
• 151867-55-9 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl methyl carbonate 
• 64339-87-3 N₄,O-bis(trimethylsilyl)-N₄-benzoylcytosine 
• 26661-13-2 4-N-benzoylcytosine 
• 918800-27-8 p-tolyl 2,3,5-tri-O-benzoyl-1-thio-β-D-ribofuranoside 
• 115459-50-2 2,3,5-Tri-O-benzoyl-D-ribofuranose 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 613-90-1 benzoyl cyanide 
• 65-46-3 CYTIDINE 
• 98-88-4 benzoyl chloride 

Downstream Products

• 6554-15-0 N⁴-benzoyl-5'-O-benzoylcytidine 
• 6554-17-2 N⁴-benzoyl-3',5'-di-O-benzoylcytidine 
• 6554-16-1 N⁴,O^2'_,O5'-tribenzoyl-cytidine 
• 74829-53-1 5,6-dihydro-N⁴-hydroxy-6-hydroxyamino-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)cytosine 
• 31652-74-1 2',3',5'-tri-O-benzoyl-L-cytidine 
• 65-46-3 CYTIDINE 
• 1748-04-5 tribenzoyl uridine 

Relevant articles and documents

Ortho-(1-phenylvinyl)benzoate glycosylation donor, and preparation method and application thereof

The invention discloses an ortho-(1-phenylvinyl)benzoate glycosylation donor, and a preparation method and an application thereof in a glycosylation reaction. The ortho-(1-phenylvinyl)benzoate glycosylation donor is stable, is easy to prepare and store, and is widely applied to the construction of various oxygen glucosides and nucleoside (nitrogen glucoside) glycosidic bonds. The leaving group ofthe donor is an alkenyl ester, has a high activity, and can be combined with thioglycoside or n-pentenyl ether glucoside through a one-pot glycosylation reaction to synthesize oligosaccharide. The glycosylation reaction conditions are mild, and receptors sensitive to acid and electrophilic reagents can tolerate the glycosylation reaction conditions.

A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor

Based on a preactivation strategy using the (p-Tol)2SO/Tf2O system, a series of nucleosides were synthesized by coupling various thioglycosides with pyrimidines and purines under mild conditions. High yields and excellent β-stereoselectivities were obtained with either armed or disarmed N-glycosylation donors by tuning the amount of (p-Tol)2SO additive.

Propargyl 1,2-orthoesters for a catalytic and stereoselective synthesis of pyrimidine nucleosides

Pyrimidine nucleosides are synthesized by using propargyl 1,2-orthoesters and Au(III) salt as a catalyst. Strategically positioned 1,2-orthoesters are found to yield only 1,2-trans nucleosides and enable preparation of 2′-OH containing pyrimidine nucleosides. The glycosyl donor employed in this study is stable and easily accessible. The identified high-yielding protocol is mild, diastereoselective, and catalytic.

A Reverse Strategy for synthesis of nucleosides based on n-pentenyl orthoester donors

Strategically derivatized NPOE glycosyl donors, are able to efficiently glycosylate silylated nucleobases under mild conditions, even as low as -78°C if necessary. Ensuring trans-1,2 glycosylation, thus permitting, unlike classical procedures, a Reverse Strategy for the synthesis of ribonucleosides, where glycosylation occurs late, rather than early, and convergency is optimized.

An efficient approach to the synthesis of nucleosides: Gold(I)-catalyzed N-glycosylation of pyrimidines and purines with glycosyl ortho-alkynyl benzoates

Persuaded with gold: The title reaction in the presence of [Ph 3PAuNTf2] (Tf=trifluoromethanesulfonyl) led conveniently to the corresponding nucleosides with excellent regioselectivity (see scheme). Even purine derivatives underwent this transformation owing to the mild conditions, which enabled the use of protecting groups that would not usually be compatible with N-glycosylation conditions. Copyright

High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries

The Vorbrueggen glycosylation reaction was adapted into a one-step 5 min/130 °C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl inflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield ± SD was 26 ± 16%, and the average purity ± SD was 95 ± 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.

Hydrothermal deamidation of 4-N-acylcytosine nucleoside derivatives: Efficient synthesis of uracil nucleoside esters

(Chemical Equation Presented) N,O-Peracylated cytidine and 2′-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125°C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.

'Green' methodology for efficient and selective benzoylation of nucleosides using benzoyl cyanide in an ionic liquid

Benzoyl cyanide in the ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate has been employed as a 'green' alternative and mild reaction condition protocol to conventional pyridine-benzoyl chloride system for efficient and selective benzoylation of nucleosides (of both the ribo- and deoxyribo-series) at ambient temperatures. The use of benzoyl cyanide-ionic liquid combination has been successfully extended for highly efficient benzoylation of phenols, aromatic amines, benzyl alcohol, aliphatic diols, 3-aminophenol and 2-aminobenzylalcohol, which indicates the versatility of this benzoylating system.

Mild, efficient, selective and "green" benzoylation of nucleosides using benzoyl cyanide in ionic liquid

Use of benzoyl cyanide (BzCN) for benzoylation of nucleosides has been studied, both in pyridine and in ionic liquid. BzCN in 1-methoxyethyl-3- methylimidazolium methanesulfonate as ionic liquid has been found to be a "green" alternative compared to the pyridine-BzCN system. An efficient and selective benzoylation of nucleosides of both, the 2′-deoxy- and the ribo-series at ambient temperature was accomplished. Copyright Taylor & Francis, Inc.

Benzoyl cyanide: A mild and efficient reagent for benzoylation of nucleosides

Efficient benzoylation of various nucleosides has been accomplished in pyridine with a catalytic amount of DMAP and benzoyl cyanide under mild conditions.