52662-10-9

Usage

InChI:InChI=1/C14H17N5O5/c1-6-3-18-12(23)8-11(17(2)14(18)16-6)19(5-15-8)13-10(22)9(21)7(4-20)24-13/h3,5,7,9-10,13,20-22H,4H2,1-2H3/t7-,9-,10-,13-/m1/s1

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 598-31-2 1-bromoacetone 
• 70230-72-7 5-(methylamino)-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide 
• 76542-73-9 5-(N-cyanomethylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide 
• 68768-32-1 3-methylguanosine 
• 68768-34-3 3,4-Dihydro-4,6-dimethyl-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-imidazo<1,2-a>purin-9-one 

Downstream Products

• 2958-98-7 3-methylguanine 
• 108274-04-0 7-methyl-3-β-D-ribofuranosylwye 
• 96881-39-9 7-methylwye 
• 68768-34-3 3,4-Dihydro-4,6-dimethyl-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-imidazo<1,2-a>purin-9-one 
• 33359-03-4 wye 
• 33359-03-4 wye 
• 36468-53-8 β-D-ribofuranose 

Relevant academic research and scientific papers

AN EFFICIENT SYNTHESIS OF Y-NUCLEOSIDE (WYOSINE) BY REGIOSPECIFIC METHYLATION OF N4-DESMETHYLWYOSINE USING ORGANOZINC REAGENT

The reaction of the organozinc reagent, produced by the reaction of CH2I2 + Zn(C2H5)2 + glyme in diethylether at 20 deg C, regioselectively methylates the N4-nitrogen of N4-desmethylwyosine-triacetate 3 to give pure wyosine-triacetate 1e in 76percent isolated yield; no trace of the isomeric N5 methylated product is found in the latter reaction.Synthesis of a new congener of Y-nucleoside 1f is also reported for the first time from compound 5 in a high overall yield using a similar procedure.

Synthesis of 3-β-D-Ribofuranosylwye, the Most Probable Structure for Wyosine from Torulopsis utilis Phenylalanine Transfer Ribonucleic Acid

Treatment of 5-(methylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide (5a) with CNBr in acetate buffer gave the 5-cyanomethylamino derivative 6a, which was cyclized to 3-methyl-guanosine (7) in the presence of NaOEt.Cyclocondensation of 7 with bromoacetone in the presence of K2CO3 provided 3-β-D-ribofuranosylwye (2), the most probable strucure for the fluorescent nucleoside from Torulopsis utilis phenylalanine transfer ribonucleic acid (tRNAPHE).The glycosidic bonds of 2 and 7 have been shown to be unusually subject to cleavage under either acidic or basic conditions, but proved to be less labile under neutral conditions, as had been reported.The base moiety of 2 is also cleaved under basic conditions.Keywords--wyosine; 3-methylguanosine; cyclocondensation; imidazole nucleoside; N-cyanation; base-catalyzed cyclization; glycosidic bond cleavage; ring fission

A Simple Synthesis of 3-β-D-Ribofuranosylwye and the Stability of its Glycosidic Bond

Treatment of 5-(methylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide (3) with CNBr followed by cyclization and reaction with bromoacetone gave 3-β-D-ribofuranosylwye (2) whose glycosidic bond was cleaved rapidly in acidic or alkaline solution, but was fairly stable at pH 5-8.5 at 37 deg C.