52662-10-9

Basic information

• Product Name: wyosine
• Synonyms: wyosine;3-(β-D-Ribofuranosyl)-4,6-dimethyl-3,4-dihydro-9H-imidazo[1,2-a]purine-9-one;3-(β-D-Ribofuranosyl)-4,6-dimethyl-3H-imidazo[1,2-a]purine-9(4H)-one;3,4-Dihydro-4,6-dimethyl-3-(β-D-ribofuranosyl)-9H-imidazo[1,2-a]purin-9-one;3-β-D-Ribofuranosyl-4,6-dimethyl-3,4-dihydro-9H-imidazo[1,2-a]purine-9-one;3-β-D-Ribofuranosyl-4,6-dimethyl-4,9-dihydro-3H-imidazo[1,2-a]purine-9-one
• CAS NO: 52662-10-9
• Molecular Formula: C₁₄H₁₇N₅O₅
• Molecular Weight: 335.31528
• Mol File: 52662-10-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 827.6°C at 760 mmHg
• Flash Point: 454.3°C
• Appearance: /
• Density: 1.86g/cm³
• Vapor Pressure: 5.13E-29mmHg at 25°C
• Refractive Index: 1.835
• PKA: 13.20±0.70(Predicted)
• CAS DataBase Reference: wyosine(CAS DataBase Reference)
• NIST Chemistry Reference: wyosine(52662-10-9)
• EPA Substance Registry System: wyosine(52662-10-9)

Safety Data

• Hazardous Substances Data: 52662-10-9(Hazardous Substances Data)

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

• 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 
• 68-12-2 N,N-dimethyl-formamide 
• 598-31-2 1-bromoacetone 
• 68768-32-1 3-methylguanosine 
• 76542-73-9 5-(N-cyanomethylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide 
• 70230-72-7 5-(methylamino)-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide 

Downstream Products

• 33359-03-4 wye 
• 36468-53-8 β-D-ribofuranose 
• 33359-03-4 wye 
• 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 
• 96881-39-9 7-methylwye 
• 108274-04-0 7-methyl-3-β-D-ribofuranosylwye 
• 2958-98-7 3-methylguanine 

Relevant articles and documents

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.

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.