3868-36-8

Basic information

• Product Name: 8-Benzyloxyguanosine
• Synonyms: 8-BENZYLOXYGUANOSINE;8-(PhenylMethoxy)guanosine;NSC 90391
• CAS NO: 3868-36-8
• Molecular Formula: C₁₇H₁₉N₅O₆
• Molecular Weight: 389.36
• Product Categories: Bases & Related Reagents;Carbohydrates & Derivatives;Metabolites & Impurities;Nucleotides
• Mol File: 3868-36-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 772°Cat760mmHg
• Flash Point: 420.7°C
• Appearance: /
• Density: 1.8g/cm³
• Refractive Index: 1.796
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly)
• CAS DataBase Reference: 8-Benzyloxyguanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Benzyloxyguanosine(3868-36-8)
• EPA Substance Registry System: 8-Benzyloxyguanosine(3868-36-8)

Safety Data

• Hazardous Substances Data: 3868-36-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Guanosine (G) derivative.

InChI:InChI=1/C17H19N5O6/c18-16-20-13-10(14(26)21-16)19-17(27-7-8-4-2-1-3-5-8)22(13)15-12(25)11(24)9(6-23)28-15/h1-5,9,11-12,15,23-25H,6-7H2,(H3,18,20,21,26)/t9-,11-,12-,15-/m1/s1

Upstream product

• 4016-63-1 8-bromoguanosine 
• 20194-18-7 sodium phenyl-methanolate 
• 118-00-3 G 
• 100-51-6 benzyl alcohol 

Downstream Products

• 151566-06-2 2',3',5'-tris((tert-butyldimethylsilyl)oxy)-8-benzyloxyguanosine 
• 3868-37-9 8-benzyloxy-xanthosine 
• 21082-30-4 9-β-(D-ribofuranosyl)-1H-purine-2,6,8(3H,7H,9H)-trione 

Relevant articles and documents

Spiroiminodihydantoin as an oxo-atom transfer product of 8-oxo-2-deoxyguanosine oxidation by chromium(V)

(Chemical Equation Presented) Oxidation of the DNA lesion 8-oxo-2′-deoxyguanosine by the two electron oxidants N,N′- ethylenebis(salicylideneanimato)oxochromium(V) (Cr(V)-salen) and bis(2-ethyl-2-hydroxybutyrato)oxochromium(V) (Cr(V)-ehba) at neutral pH f

Oxidation of 9-β-d-ribofuranosyl uric acid by one-electron oxidants versus singlet oxygen and its implications for the oxidation of 8-oxo-7,8-dihydroguanosine

Uric acid, a cellular antioxidant, undergoes oxidation in the presence of one-electron oxidants as well as singlet oxygen. In the present work, the oxidation pathways and products formed from oxidation of the uric acid nucleoside are compared to the more commonly studied uric acid free base. A wider distribution of products, including allantoin, urea, caffolide, and 5-carboxamido-5-hydroxyhydantoin nucleosides, are formed when the N9 position of uric acid is glycosylated. The oxidation pathways share some features in common with the oxidation of 8-oxo-7,8-dihydroguanosine, but the additional spectrum of products implies that the combination of oxidative and deaminative damage to guanosine may lead to a more complex set of DNA lesions than originally described.

8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells

A variety of 8-substituted guanosine and 2'-deoxyguanosine derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells in culture. The most active agents in the guanosine series were 8-substituted -N(CH3)2, -NHCH3, -NH2, -OH, and -SO2CH3, which caused 68, 42, 34, 33, and 30% of erythroleukemia cells to attain benzidine positivity, a functional measure of maturation, at concentrations of 5, 1, 0.4, 5, and 5 mM, respectively. The 8-OH derivative of the 2'-deoxyguanosine series produced comparable activity, causing 62% benzidine-positive cells at a level of 0.2 mM. These findings indicate that 8-substituted analogues of guanosine and 2'-deoxyguanosine have the potential to terminate leukemia cell proliferation through conversion to end-stage differentiated cells.