O6-Benzyl Guanosine

Base Information

• Chemical Name: O6-Benzyl Guanosine
• CAS No.: 4552-61-8
• Molecular Formula: C17H19N5O5
• Molecular Weight: 373.368
• Mol file: 4552-61-8.mol

Synonyms:2-Amino-6-(benzyloxy)-9-|A-D-ribofuranosyl-purine;O6-Benzylguanosine;6-O-(Phenylmethyl)guanosine;

Chemical Property of O6-Benzyl Guanosine

Chemical Property:

• Melting Point: 135-141°C
• PSA: 149.50000
• LogP: -0.47090
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol (Sparingly)

Purity/Quality:

98%Min ^*data from raw suppliers

O6-Benzyl guanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of O6-Benzyl Guanosine

There total 17 articles about O6-Benzyl 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: 93.0%

O6-benzyl-N2,2',3',5'-tetraisobutyrylguanosine (148437-88-1) → 2-amino-6-benzyloxy-9-β-D-ribofuranosylpurine (4552-61-8)

Guidance literature:

With sodium hydroxide; In methanol; for 48h; Ambient temperature;

DOI:10.1021/jo00061a033

Reference yield: 92.0%

5'-O,3'-O,2'-O-tris(tert-butyldimethylethylsilyl)-6-O-benzylguanosine (253779-52-1) → 2-amino-6-benzyloxy-9-β-D-ribofuranosylpurine (4552-61-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/jo991153b

Reference yield: 70.0%

N-[6-Benzyloxy-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-acetamide (156998-80-0) → 2-amino-6-benzyloxy-9-β-D-ribofuranosylpurine (4552-61-8)

Guidance literature:

With sodium hydroxide; In pyridine; at 30 ℃; for 2h;

DOI:10.1021/jm960881d

upstream raw materials:

G

N-nitroso-N-benzylurea

O⁶-benzyl-N²,2',3',5'-tetraisobutyrylguanosine

N-[6-Benzyloxy-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-acetamide

Downstream raw materials:

N₂,N₂-dimethylguanosine

2-dimethylamino-6-benzyloxy-9-β-D-ribofuranosylpurine

O⁶-Benzyl-N²,3-etheno-2'-O--3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine

O⁶-Benzyl-N²,3-etheno-3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine

Refernces

• 1、 Li, Hui,Miller, Marvin J.. "Syntheses of 5′-Deoxy-5′-N-hydroxylaminopyrimidine and Purine Nucleosides: Building Blocks for Novel Antisense Oligonucleosides with Hydroxamate Linkages". . p. 9289 - 9293. Retrieved 2007/10/03.
• 2、 Khazanchi,Yu,Johnson. "N2,3-etheno-2'-deoxyguanosine [8,9-dihydro-9-oxo-2'-deoxy-3-β-D-ribofuranosylimidazo[2,1-b]purine]: A practical synthesis and characterization". . p. 2552 - 2556. Retrieved 2007/10/02.