66781-54-2

Basic information

• Product Name: Guanosine, N-benzoyl-, 2',3',5'-triacetate
• CAS NO: 66781-54-2
• Molecular Formula: C23H23N5O9
• Molecular Weight: 513.464
• Mol File: 66781-54-2.mol

Chemical Properties

• CAS DataBase Reference: Guanosine, N-benzoyl-, 2',3',5'-triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Guanosine, N-benzoyl-, 2',3',5'-triacetate(66781-54-2)
• EPA Substance Registry System: Guanosine, N-benzoyl-, 2',3',5'-triacetate(66781-54-2)

Safety Data

• Hazardous Substances Data: 66781-54-2(Hazardous Substances Data)

Upstream product

• 90742-11-3 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-benzoylamino-6-dimethylthiocarbamoyloxy-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 28288-50-8 N²,O^2',O^3',O^5'-tetrabenzoylguanosine 
• 108-24-7 acetic anhydride 
• 1234319-81-3 2',3',5'-tri-O-acetyl-2-N-benzoyl-6-O-benzylguanosine 

Downstream Products

• 76887-35-9 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-benzoylamino-6-(3-nitro-[1,2,4]triazol-1-yl)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 80354-13-8 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-benzoylamino-6-(diphenoxy-phosphoryloxy)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 76994-80-4 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-benzoylamino-6-(2,4,6-triisopropyl-benzenesulfonyloxy)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 66781-55-3 3',5'-di-O-acetyl-N²-benzoylguanosine 
• 76994-80-4 Acetic acid (3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-benzoylamino-6-(2,4,6-triisopropyl-benzenesulfonyloxy)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 90742-10-2 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-benzoylamino-6-diphenylcarbamoyloxy-purin-9-yl)-tetrahydro-furan-3-yl ester 

Relevant articles and documents

Synthetic (p)ppGpp analogue is an inhibitor of stringent response in mycobacteria

Bacteria elicit an adaptive response against hostile conditions such as starvation and other kinds of stresses. Their ability to survive such conditions depends, in part, on stringent response pathways. (p)ppGpp, considered to be the master regulator of t

15N double-labeled guanosine from inosine through ring-opening-ring-closing and one-pot Pd-catalyzed C-O and C-N cross-coupling reactions

(Figure Presented) [N,1-15N2]-Guanosine, or [1,NH2-15N2]-guanosine, and derivatives were prepared from tri-O-acetylinosine, via N-nitration and reaction with 15NH2OH, followed by conversion of the 15N-labeled 1-hydroxyinosine to the corresponding 2,6-dichloropurine riboside. The sequential one-pot C-O and C-N key couplings of this dichloro derivative with PhCH2OH and PhCO15NH2 or iPrCO15NH2 was achieved in good overall yields, with Pd(0)-Xantphos as the best choice of five different catalytic systems examined.

Synthesis of a Dodecaribonucleotide, GUAUCAAUAAUG, by Use of "Fully" Protected Ribonucleotide Building Blocks

The fully protected ribonucleotide monomer units (17, 19, 26, and 32) have been synthesized in excellent overall yields from unprotected ribonucleosides.Several carbamoyl groups were tested for protection of the guanosine base moiety.Finally, the diphenylcarbamoyl group was chosen and O6-(diphenylcarbamoyl)-N2-propionylguanosine was readily prepared in high yield and converted to the guanosine units 12 and 17.The uridine unit 19 was prepared by the acylation of the previous unit 18 with anisoyl chloride in the presence of i-Pr2EtN.In the case of the adenosine and cytidine units (26 and 32) , the regioselective 2'-O-tetrahydropyranylation was involved in their syntheses.These "perfectly" protected monomer units have succesfully been utilized in the synthesis of GUAUCAAUAAUG, a modified 5'-terminal structure, of brome mosic virus (BMV) mRNA no. 4 filament.The dodecamer chain was elongated by fragment condensation from the 3'-5' direction.The yields of the oligomer blocks have proved to be dramatically high because no side reactions occurred during the condensation reactions.Indeed, the final coupling to give the target 12-mer was achieved in 91percent yield.The deprotection of the fully protected in the usual manner gave GUAUCAAUAAUG in ca. 30percent yield.

4-CHLOROPHENYL 5-CHLORO-8-QUINOLYL HYDROGEN PHOSPHATE: A USEFUL PHOSPHORYLATING AGENT FOR GUANOSINE 3'-PHOSPHOTRIESTER

5'-O-Dimethoxytrityl-2'-O-tetrahydropyranyl-N2-benzoylguanosine smoothly reacts with 4-chlorophenyl 5-chloro-8-quinolyl hydrogen phosphate in the presence of 8-quinolinesulfonyltetrazolide (QS-te) to give 5'-O-dimethoxytrityl-2'-O-tetrahydropyr