69471-51-8

Basic information

• Product Name: Guanosine, N-(triphenylmethyl)-, 2',3',5'-triacetate
• CAS NO: 69471-51-8
• Molecular Formula: C35H33N5O8
• Molecular Weight: 651.676
• Mol File: 69471-51-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Guanosine, N-(triphenylmethyl)-, 2',3',5'-triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Guanosine, N-(triphenylmethyl)-, 2',3',5'-triacetate(69471-51-8)
• EPA Substance Registry System: Guanosine, N-(triphenylmethyl)-, 2',3',5'-triacetate(69471-51-8)

Safety Data

• Hazardous Substances Data: 69471-51-8(Hazardous Substances Data)

Upstream product

• 76-83-5 trityl chloride 
• 6979-94-8 2',3',5'-tri-O-acetyl-guanosine 
• 76994-72-4 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-[bis-(4-chloro-phenoxy)-phosphoryloxy]-2-(trityl-amino)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 76998-80-6 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(diphenoxy-phosphoryloxy)-2-(trityl-amino)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 76994-83-7 Acetic acid (3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(tert-butyl-diphenyl-silanyloxy)-2-(trityl-amino)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 76994-73-5 Acetic acid (3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(diisopropoxy-phosphoryloxy)-2-(trityl-amino)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 76994-75-7 Acetic acid (3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(dibutyl-phosphinothioyloxy)-2-(trityl-amino)-purin-9-yl]-tetrahydro-furan-3-yl ester 

Downstream Products

• 76994-73-5 Acetic acid (3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(diisopropoxy-phosphoryloxy)-2-(trityl-amino)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 76994-73-5 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(diisopropoxy-phosphoryloxy)-2-(trityl-amino)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 76998-80-6 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(diphenoxy-phosphoryloxy)-2-(trityl-amino)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 90742-07-7 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-dimethylcarbamoyloxy-2-(trityl-amino)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 76994-78-0 Acetic acid (2R,3S,4R)-5-[6-(dibutyl-phosphinothioyloxy)-2-(trityl-amino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 
• 76994-77-9 Dibutyl-phosphinothioic acid O-[9-((3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-(trityl-amino)-9H-purin-6-yl] ester 
• 76994-81-5 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-amino-6-(2,4,6-triisopropyl-benzenesulfonyloxy)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 76994-78-0 Acetic acid (2R,3S,4R,5R)-5-[6-(dibutyl-phosphinothioyloxy)-2-(trityl-amino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 
• 76994-77-9 Dibutyl-phosphinothioic acid O-[9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-(trityl-amino)-9H-purin-6-yl] ester 
• 66107-69-5 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-O-p-toluenesulfonylguanine 
• 98151-62-3 2',3',5'-tri-O-acetylguanoside 
• 6979-94-8 2-amino-6-hydroxyl-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 66107-67-3 2',3',5-tri-O-acetyl-O⁶-meritylsulfonylguanosine 
• 76994-75-7 2',3',5'-tri-O-acetyl-O⁶-dibutylposphinothioyl-N²-tritylguanosine 

Relevant articles and documents

Structure and synthesis of 6-(substituted-imidazol-1-yl)purines: Versatile substrates for regiospecific alkylation and glycosylation at N9

X-ray crystal structures of several 6-(azolyl)purine base and nucleoside derivatives show essentially coplanar conformations of the purine and appended 6-(azolyl) rings. However, the planes of the purine and imidazole rings are twisted ～57° in a 2-chloro-6-(4,5-diphenylimidazol-1-yl)purine nucleoside, and a twist angle of ～61° was measured between the planes of the purine and pyrrole rings in the structure of a 6-(2,5-dimethylpyrrol-1-yl) purine nucleoside derivative. Shielding "above" N7 of the purine ring by a proximal C-H on the 6-azolyl moiety is apparent with the coplanar compounds, but this effect is diminished in those without coplanarity. Syntheses of 6-(azolyl)purines from both base and nucleoside starting materials are described. Treatment of 2,6-dichloropurine with imidazole gave 2-chloro-6-(imidazol-1-yl)purine. Modified Appel reactions at C6 of trityl-protected hypoxanthine and guanine derivatives followed by detritylation gave 6-(imidazol-1-yl)- and 2-amino-6-(imidazol-1-yl)purines. Imidazole was introduced at C6 of 2′,3′,5′-tri-O-acetylinosine by a modified Appel reaction, and solvolysis of the glycosyl linkage gave 6-(imidazol-1-yl)purine. Guanosine triacetate was transformed into the protected 2,6-dichloropurine nucleoside, which was subjected to SNAr displacement with imidazoles at C6 followed by glycosyl solvolysis to provide 2-chloro-6-(substituted-imidazol-1-yl)purines. Potential applications of these purine derivatives are outlined.

NEW GUANOSINE DERIVATIVES: FACILE O6-PHOSPHORYLATION, THIOPHOSPHINYLATION, SULPHONYLATION AND SILYLATION OF GUANOSINE DERIVATIVES BY 4-DIMETHYLAMINOPYRIDINE CATALIZED REACTION

Appropriately protected guanosine derivatives were successfully converted to the corresponding O6-substituted guanosine derivatives by treatment with dialkyl- or diaryl-phosphoryl halides, dialkyl- or diaryl-phosphinothioyl halides, arenesulfon