ChemicalBook CAS DataBase List 2'-O-Methylguanosine

2'-O-Methylguanosine synthesis

12synthesis methods

Product Name:2'-O-Methylguanosine
CAS Number:2140-71-8
Molecular formula:C11H15N5O5
Molecular Weight:297.27

8-Thio-2'-O-methylguanosine (1 mmole) is dissolved in water and the solution is heated at reflux with Raney nickel for 6 h. The product is isolated by passing the solution through a short pad of celite and is further crystallizing to afford 2'-O-methylguanosine.

280-57-9 Synthesis

280-57-9
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$5.00/5g

194034-59-8 Synthesis

2-AMino-6-chloropurine-9-(2'-O-Methyl)riboside

194034-59-8
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$1066.00/1g

2140-71-8
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$20.19/250mg

Yield:2140-71-8 1.25 g (65%)

Reaction Conditions:

in water;

Steps:

9 2'-O-Methyl Guanosine (9)

2'-O-Methyl Guanosine (9) A mixture of 5 (2.05 g, 6.5 mmol), 1,4-diazabicyclo[2.2.2]octane (1 equiv.) and water (30 mL) was heated to 90° C. for 45 minutes. Then the solution was cooled to ambient temperature, basified to pH 12 with 2M NaOH, and washed with methylene chloride (3*60 mL). The aqueous phase was acidified to pH 6 with 6M HCl and left at refrigerator overnight. Formed precipitate was filtered off. Mother liquor was evaporated to dryness, the residue was dissolved in water and applied to the short column with RP-18 silica gel. Solid phase was washed with water and remaining product was eluted with 5% aq methanol. Appropriate fractions were combined, evaporated to dryness and recrystallized from to provide 1.25 g (65%) of 2'-O-methyl guanosine 9. Analytical sample was recrystallized from water, m.p. The product was identical to authentic sample by HPLC, UV, ¹ H-NMR-spectroscopy. 3',5'-di-O-Acetyl-2'-O-Methyl-6-Chloropurine Riboside (7)

References:

US5962675,1999,A

80791-87-3 Synthesis