N2-Benzoyl-D-guanosine

Base Information

• Chemical Name: N2-Benzoyl-D-guanosine
• CAS No.: 3676-72-0
• Molecular Formula: C17H17N5O6
• Molecular Weight: 387.352
• Hs Code.: 29389090
• Mol file: 3676-72-0.mol

Synonyms:Benzamide,N-(1,6-dihydro-6-oxo-9-b-D-ribofuranosyl-9H-purin-9-yl)- (8CI);2-N-Benzoylguanosine;N-Benzoylguanosine;

Chemical Property of N2-Benzoyl-D-guanosine

Chemical Property:

• Appearance/Colour: Off-white solid
• Melting Point: 255-256oC
• Refractive Index: 1.809
• PSA: 162.59000
• Density: 1.8 g/cm³
• LogP: -0.94360
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

97% ^*data from raw suppliers

N2-Benzoylguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N2-Benzoyl-D-guanosine is a useful building block for oligoribonucleotide synthesis.

Technology Process of N2-Benzoyl-D-guanosine

There total 13 articles about N2-Benzoyl-D-guanosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2'-O-(4-methoxybenzyl)-N2-benzoylguanosine (80015-56-1) → N2-benzoylguanosine (3676-72-0)

Guidance literature:

With trityl tetrafluoroborate; In nitromethane; water; for 1.5h; Ambient temperature;

DOI:10.1021/jo00175a010

Reference yield: 94.0%

N2,O2',O3',O5'-tetrabenzoylguanosine (28288-50-8) → N2-benzoylguanosine (3676-72-0)

Guidance literature:

With pyridine; potassium hydroxide; In ethanol; at 0 ℃; for 0.0833333h;

Reference yield:

N-[9-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-benzamide → N2-benzoylguanosine (3676-72-0)

Guidance literature:

With ammonium hydroxide; In pyridine; at 25 ℃; for 0.25h; Yield given;

DOI:10.1055/s-1985-31198

upstream raw materials:

N²,O^2',O^3',O^5'-tetrabenzoylguanosine

2'-O-(4-methoxybenzyl)-N²-benzoylguanosine

benzoyl chloride

G

Downstream raw materials:

Phosphoric acid (2R,3R,4R,5R)-5-(2-benzoylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(4-methoxy-benzyloxy)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 5-chloro-quinolin-8-yl ester

Phosphoric acid (2R,3R,4R,5R)-5-(2-benzoylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 5-chloro-quinolin-8-yl ester

N-{9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-benzamide

2'-O-(4-methoxybenzyl)-3',5'-di-O-acetyl-N²-benzoylguanosine

Refernces

• 1、 Zhu, Xue-Feng,Williams Jr., Howard J.,Scott, A. Ian. "An improved transient method for the synthesis of N-benzoylated nucleosides". . p. 1233 - 1243. Retrieved 2007/10/03.
• 2、 Nukaya,Inaoka,Ishida,Tsuji,Suwa,Wakabayashi,Kosuge. "Modification of the amino group of guanosine by methylglyoxal and other α-ketoaldehydes in the presence of hydrogen peroxide". . p. 649 - 653. Retrieved 2007/10/02.