5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-methoxyethyl)-5-methylcytidine synthesis

7synthesis methods

Product Name:5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-methoxyethyl)-5-methylcytidine
CAS Number:182496-00-0
Molecular formula:C34H39N3O8
Molecular Weight:617.6888

2(1H)-Pyrimidinone, 1-[3-O-acetyl-5-O-[bis(4-methoxyphenyl)phenylmethyl]-2-O-(2-methoxyethyl)-β-D-ribofuranosyl]-5-methyl-4-(1H-1,2,4-triazol-1-yl)-

182495-99-4
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5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-methoxyethyl)-5-methylcytidine

182496-00-0
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Yield:182496-00-0 95%

Reaction Conditions:

Stage #1: 3'-O-acetyl-2'-O-methoxyethyl-5'-O-(4,4'-dimethoxytrityl)-5-methyl-4-triazoleuridinewith ammonia;water in 1,4-dioxane at 20; for 2 h;
Stage #2: with ammonia in methanol at 100; for 2 h;

Steps:

1 2'-O-Methoxyethyl-5'-O-dimethoxytrityl-5-methylcytidine

2'-O-Methoxyethyl-5'-O-dimethoxytrityl-5-methylcytidine A solution of 3'-O-acetyl-2'-O-methoxyethyl-5'-O-dimethoxytrityl-5-methyl-4-triazoleuridine (103 g, 0.141 M) in dioxane (500 mL) and NH₄OH (30 mL) was stirred at room temperature for 2 hours. The dioxane solution was evaporated and the residue azeotroped with MeOH (2*200 mL). The residue was dissolved in MeOH (300 mL) and transferred to a 2 liter stainless steel pressure vessel. MeOH (400 mL) saturated with NH₃ gas was added and the vessel heated to 100° C. for 2 hours (TLC showed complete conversion). The vessel contents were evaporated to dryness and the residue was dissolved in EtOAc (500 mL) and washed once with saturated NaCl (200 mL). The organics were dried over sodium sulfate and the solvent was evaporated to give 85 g (95%) of the title compound.

References:

US2004/77083,2004,A1 Location in patent:Page 17