163759-49-7

Basic information

• Product Name: 2'-O-(2-Methoxyethyl)-5-methyluridine
• Synonyms: 2'-O-(2-Methoxyethyl)-5-methyluridine;5-Me-2'-O-MOE U;Uridine, 2'-O-(2-Methoxyethyl)-5-Methyl-;5-Me-2'-O-MOE Uridine;2'-O-(2-Methoxyethy)-5-methyluridine
• CAS NO: 163759-49-7
• Molecular Formula: C₁₃H₂₀N₂O₇
• Molecular Weight: 316.3071
• EINECS: 500-100-4
• Mol File: 163759-49-7.mol
• Article Data: 415

Chemical Properties

• Melting Point: 115.5-116.5 °C
• Appearance: /
• Density: 1.41
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
• PKA: 9.55±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2'-O-(2-Methoxyethyl)-5-methyluridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-O-(2-Methoxyethyl)-5-methyluridine(163759-49-7)
• EPA Substance Registry System: 2'-O-(2-Methoxyethyl)-5-methyluridine(163759-49-7)

Safety Data

• Hazardous Substances Data: 163759-49-7(Hazardous Substances Data)

Usage

Uses

2'-O-(2-Methoxyethyl)-5-methyluridine is a protected uridine derivative (U829910) and nucleoside used in the preparation of synthetic nucleic acids.

Synthesis

2,2'-Anhydro-5-methyluridine (195 g, 0.81 M), tris(2-methoxyethyl)borate (231 g, 0.98 M) and 2-methoxyethanol (1.2 L) were added to a 2 L stainless steel pressure vessel and placed in a pre-heated oil bath at 160°C. After heating for 48 hours at 155-160°C, the vessel was opened and the solution evaporated to dryness and triturated with methanol (200 mL). The residue was suspended in hot acetone (1 L). The insoluble salts were filtered, washed with acetone (150 mL) and the filtrate evaporated. The residue (280 g) was dissolved in CH3CN (600 mL) and evaporated. A silica gel column (3 kg) was packed in CH2Cl2/ acetone/methanol (20:5:3) containing 0.5% Et3NH. The residue was dissolved in CH2Cl2 (250 mL) and adsorbed onto silica (150 g) prior to loading onto the column. The product was eluted with the packing solvent to give product. Yield 160 g, 63%.

Synthetic route

O-2,2'-cyclo-5-methyluridine (22423-26-3) + tris(2-methoxyethyl)borate (14983-42-7) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
Stage #1: O-2,2'-cyclo-5-methyluridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	69.4%
Stage #1: O-2,2'-cyclo-5-methyluridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	69.4%
Stage #1: O-2,2'-cyclo-5-methyluridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	69.4%

O-2,2'-cyclo-5-methyluridine (22423-26-3) + tris(2-methoxyethyl)borate (14983-42-7) → C23H32N4O12 + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
Stage #1: O-2,2'-cyclo-5-methyluridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	A n/a B 69.4%
Stage #1: O-2,2'-cyclo-5-methyluridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	A n/a B 69.4%
Stage #1: O-2,2'-cyclo-5-methyluridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Heating / reflux; Stage #2: With water for 0.5h; Heating / reflux;	A 15 %Chromat. B 69.4%

O2-2'-anhydro-5-methyluridine + tris(2-methoxyethyl)borate (14983-42-7) → C23H32N4O12 + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
Stage #1: O2-2'-anhydro-5-methyluridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Heating / reflux; Stage #2: With water for 0.5h; Heating / reflux;	A 15 %Chromat. B 69.4%
Stage #1: O2-2'-anhydro-5-methyluridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Heating / reflux; Stage #2: With water for 0.5h; Heating / reflux;	A 15 %Chromat. B 69.4%
Stage #1: O2-2'-anhydro-5-methyluridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Heating / reflux; Stage #2: With water for 0.5h; Heating / reflux;	A 15 %Chromat. B 69.4%

O-2,2'-cyclo-5-methyluridine (22423-26-3) + tris(2-methoxyethyl)borate (14983-42-7) → C23H32N4O12 + thymin (65-71-4) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
Stage #1: O-2,2'-cyclo-5-methyluridine; tris(2-methoxyethyl)borate; sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	A n/a B n/a C 69.4%
Stage #1: O-2,2'-cyclo-5-methyluridine; tris(2-methoxyethyl)borate; sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	A n/a B n/a C 69.4%

O2-2'-anhydro-5-methyluridine (947322-40-9) + tris(2-methoxyethyl)borate (14983-42-7) → C23H32N4O12 + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
Stage #1: O2-2'-anhydro-5-methyluridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	A 15 %Chromat. B 69.4%
Stage #1: O2-2'-anhydro-5-methyluridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	A 15 %Chromat. B 69.4%
With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h;	A n/a B 69.4%

O2-2'-anhydro-5-methyluridine (947322-40-9) + tris(2-methoxyethyl) borate → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
Stage #1: O2-2'-anhydro-5-methyluridine; tris(2-methoxyethyl) borate With 2-methoxy-ethanol; sodium hydrogencarbonate at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	69.4%
With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h;	69.4%

O2-2'-anhydro-5-methyluridine + tris(2-methoxyethyl)borate (14983-42-7) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
Stage #1: O2-2'-anhydro-5-methyluridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Heating / reflux; Stage #2: With water for 0.5h; Heating / reflux;	69.4%

O2-2'-anhydro-5-methyluridine (947322-40-9) + tris(2-methoxyethyl)borate (14983-42-7) + 2-methoxy-ethanol (109-86-4) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
Stage #1: O2-2'-anhydro-5-methyluridine; tris(2-methoxyethyl)borate; 2-methoxy-ethanol With sodium hydrogencarbonate at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	69.4%
With sodium hydrogencarbonate at 130℃; for 21h;	69.4%
Stage #1: O2-2'-anhydro-5-methyluridine; tris(2-methoxyethyl)borate; 2-methoxy-ethanol With sodium hydrogencarbonate at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	69.4%
at 155 - 160℃; for 48h;	63%

tris(2-methoxyethyl)borate (14983-42-7) + 2,2'-anhydro-1-(β-D-arabinofuranosyl)thymine (215713-37-4) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
Stage #1: tris(2-methoxyethyl)borate; 2,2'-anhydro-1-(β-D-arabinofuranosyl)thymine With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: In water at 100℃; for 0.5h;	69.4%

1-[(2R,3R,4R,5R)-4-(2,4-Dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (168427-88-1) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
With hydrogen; sodium acetate; palladium on activated charcoal In methanol at 45℃; under 2250.2 Torr;	94%

2,2'-anhydro-5-methyl-uridine + tris(2-methoxyethyl)borate (14983-42-7) → C23H32N4O12 + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
Stage #1: 2,2'-anhydro-5-methyl-uridine; tris(2-methoxyethyl)borate With sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	A n/a B 69.4%

2,2'-anhydro-5-methyluridine + 2-methoxy-ethanol (109-86-4) → C23H32N4O12 + thymin (65-71-4) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
Stage #1: 2,2'-anhydro-5-methyluridine; 2-methoxy-ethanol With tris(2-methoxyethyl)borate; sodium hydrogencarbonate at 130℃; under 760.051 Torr; for 21h; Argon atmosphere; Stage #2: With water for 0.5h; Heating / reflux;	A n/a B n/a C 69.4%

O-2,2'-cyclo-5-methyluridine (22423-26-3) + 2-methoxy-ethanol (109-86-4) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
With tris(2-methoxyethyl)borate; sodium hydrogencarbonate at 130℃; for 18h; atmospheric pressure;	75%
With tris(2-methoxyethyl)borate at 155 - 160℃; for 48h;	63%

O2-2'-anhydro-5-methyluridine (947322-40-9) + 2-methoxy-ethanol (109-86-4) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
With tris(2-methoxyethyl) borate; sodium hydrogencarbonate at 130℃; for 21h;	69.4%

O-2,2'-cyclo-5-methyluridine (22423-26-3) + tris(2-methoxyethyl) borate → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
In 2-methoxy-ethanol at 155 - 160℃; for 48h;	63%

2,2'-Anhydro-5-methyluridine + tris(2-methoxyethyl)borate (14983-42-7) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
In 2-methoxy-ethanol at 155 - 160℃; for 48h;	63%

tris(2-methoxyethyl)borate (14983-42-7) + thymidine (50-89-5) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
In 2-methoxy-ethanol; water at 155 - 160℃; for 48h;	63%

O-2,2'-cyclo-5-methyluridine (22423-26-3) → thymin (65-71-4) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
With tris(2-methoxyethyl)borate; sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h;	A 2% B n/a

3',5'-di-O-levulinyl-2'-O-(2-methoxyethyl)-5-methyluridine (440327-51-5) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) + 3'-O-levulinyl-2'-O-(2-methoxyethyl)-5-methyluridine

Conditions	Yield
With Candida antarctica lipase B; phosphate buffer In 1,4-dioxane at 40℃; for 96h; pH=7;	A n/a B 84%

O-2,2'-cyclo-5-methyluridine (22423-26-3) + tris(2-methoxyethyl)borate (14983-42-7) + 2-methoxy-ethanol (109-86-4) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
at 155 - 160℃; for 48h;	63%
at 155 - 160℃; for 48h;	160 g

O-2,2'-cyclo-5-methyluridine (22423-26-3) + Et3NH + tris(2-methoxyethyl)borate (14983-42-7) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
In dichloromethane; 2-methoxy-ethanol; acetone; acetonitrile
In dichloromethane; 2-methoxy-ethanol; acetone; acetonitrile
In dichloromethane; 2-methoxy-ethanol; acetone; acetonitrile

O-2,2'-cyclo-5-methyluridine (22423-26-3) + Et3 NH + tris(2-methoxyethyl)borate (14983-42-7) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
In dichloromethane; 2-methoxy-ethanol; acetone; acetonitrile
In dichloromethane; 2-methoxy-ethanol; acetone; acetonitrile	160 g (63%)
In dichloromethane; 2-methoxy-ethanol; acetone; acetonitrile

3',5'-di-O-levulinyl-2'-O-(2-methoxyethyl)-5-methyluridine (440327-51-5) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) + 3'-O-levulinyl-2'-O-(2-methoxyethyl)-5-methyluridine + 5'-O-levulinyl-2'-[(2-methoxyethyl)oxy]thymidine

Conditions	Yield
With phosphate buffer; Pseudomonas cepacia lipase In 1,4-dioxane at 40℃; for 168h; pH=7;	A n/a B n/a C 79%

3'-O-Acetyl-2'-O-(2-methoxyethyl)-5-methyl-5'-O-(4-phenylbenzoyl)uridin (553664-34-9) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
With sodium methylate In methanol at 20℃; for 1h;	91%

O-2,2'-cyclo-5-methyluridine (22423-26-3) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
With tris(2-methoxyethyl)borate; 2-methoxy-ethanol at 155 - 160℃; for 48h;

O-2,2'-cyclo-5-methyluridine (22423-26-3) + Et3NH + tris(2-methoxyethyl)borate (14983-42-7) + chloro-bis-(2-methoxy-phenyl)-phenyl-methane (854751-16-9) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
In pyridine; methanol; dichloromethane; chloroform; 2-methoxy-ethanol; acetone; acetonitrile
In pyridine; methanol; dichloromethane; chloroform; 2-methoxy-ethanol; acetone; acetonitrile
In pyridine; methanol; dichloromethane; chloroform; 2-methoxy-ethanol; acetone; acetonitrile

O-2,2'-cyclo-5-methyluridine (22423-26-3) + Et3NH → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
In dichloromethane; 2-methoxy-ethanol; acetone; acetonitrile	160 g (63%)

O-2,2'-cyclo-5-methyluridine (22423-26-3) + tris(2-methoxyethyl)boarate + Et3NH → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
In dichloromethane; 2-methoxy-ethanol; acetone; acetonitrile	160 g (63%)

O-2,2'-cyclo-5-methyluridine (22423-26-3) + Et3NH + (2 methoxyethyl)borate (66407-44-1) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
In dichloromethane; 2-methoxy-ethanol; acetone; acetonitrile

O-2,2'-cyclo-5-methyluridine (22423-26-3) + Et3NH + tris(2-methoxyethyl)borate (14983-42-7) + 2-methoxy-ethanol (109-86-4) → 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7)

Conditions	Yield
In dichloromethane; acetone; acetonitrile	160 g (63%)

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) → 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridine (163759-50-0)

Conditions	Yield
With 2,6-dimethylpyridine In acetonitrile at -10 - 0℃;	96%
With lutidine In acetonitrile at -10 - 3℃; for 1.41667h;	96%
With lutidine In acetonitrile at -10 - 3℃; for 1.41667h;	96%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) → 3',5'-bis DMT + 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridine (163759-50-0)

Conditions	Yield
With lutidine In acetonitrile at -10 - 3℃; for 1.41667h;	A n/a B 96%
With pyridine

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) → 3',5'-bis DMT + 5'-O-dimethoxytrityl-2'-O-(2-methoxyethyl)-5-methyl-uridine + bis(4-methoxyphenyl)phenylmethyl methyl ether (125016-87-7)

Conditions	Yield
With lutidine In acetonitrile at -10 - -2℃; for 1h;	A 0.44 %Chromat. B 96% C 0.06 %Chromat.
With lutidine In acetonitrile at -10 - -2℃; for 1h;	A 0.44 %Chromat. B 96% C 0.06 %Chromat.

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) → 5'-O-dimethoxytrityl-2'-O-(2-methoxyethyl)-5-methyl-uridine + C53H52N2O9 + bis(4-methoxyphenyl)phenylmethyl methyl ether (125016-87-7)

Conditions	Yield
With lutidine In acetonitrile at -2 - 3℃; for 1.4h;	A 96% B n/a C n/a

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) → bis(4-methoxyphenyl)phenylmethyl methyl ether (125016-87-7) + 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridine (163759-50-0)

Conditions	Yield
With lutidine In acetonitrile at -10 - 3℃; for 1.5h;	A n/a B 96%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) → 3',5'-bis DMT + 3-(di-4-anisylphenylmethyl)-6-(di-4-anisylmethylene)-1,4-cyclohexadiene (102343-05-5) + bis(4-methoxyphenyl)phenylmethyl methyl ether (125016-87-7) + 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridine (163759-50-0)

Conditions	Yield
With 2,6-dimethylpyridine In acetonitrile at -15 - 3℃; for 1.41667 - 1.5h;	A n/a B n/a C n/a D 96%

methanol (67-56-1) + 4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) → 3',5'-bis DMT + bis(4-methoxyphenyl)phenylmethyl methyl ether (125016-87-7) + 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridine (163759-50-0)

Conditions	Yield
Stage #1: 4,4'-dimethoxytrityl chloride; 2'-O-(2-methoxyethyl)-5-methyluridine With 2,6-dimethylpyridine In acetonitrile at -10 - -3℃; for 1.41667h; Stage #2: methanol In acetonitrile for 0.166667h;	A n/a B n/a C 96%
Stage #1: 4,4'-dimethoxytrityl chloride; 2'-O-(2-methoxyethyl)-5-methyluridine With 2,6-dimethylpyridine In acetonitrile at -10 - 3℃; for 1.41667h; Stage #2: methanol In acetonitrile for 0.166667h;	A n/a B n/a C 96%

levulinic acid (123-76-2) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) → 3',5'-di-O-levulinyl-2'-O-(2-methoxyethyl)-5-methyluridine (440327-51-5)

Conditions	Yield
With dmap; triethylamine; dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃; for 2h;	95%

succinic acid anhydride (108-30-5) + 4,4'-dimethoxytrityl chloride (40615-36-9) + triethylamine (121-44-8) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) → triethylammonium 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-methoxyethyl)-5-methyluridine-3'-O-succinate (730979-84-7)

Conditions	Yield
Stage #1: 4,4'-dimethoxytrityl chloride; 2'-O-(2-methoxyethyl)-5-methyluridine With 2,6-dimethylpyridine In acetonitrile at 20℃; for 0.5h; Stage #2: With methanol In acetonitrile for 0.166667h; Stage #3: succinic acid anhydride; triethylamine In acetonitrile	90%

p-methoxy-benzyl 2,7-dimethyl pixyl ether + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) → 5'-dimethylpixyl-2'-methoxyethylribothymidine

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 0.666667h; Molecular sieve; Inert atmosphere; regiospecific reaction;	87%

2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) + O-levulinyl acetonoxime (647834-80-8) → 5'-O-levulinyl-2'-[(2-methoxyethyl)oxy]thymidine

Conditions	Yield
With Candida antarctica lipase B In tetrahydrofuran at 40℃; for 7h;	70%
With Candida antarctica lipase B In tetrahydrofuran

2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) + O-levulinyl acetonoxime (647834-80-8) → 3'-O-levulinyl-2'-O-(2-methoxyethyl)-5-methyluridine + 5'-O-levulinyl-2'-[(2-methoxyethyl)oxy]thymidine

Conditions	Yield
With Pseudomonas cepacia lipase In tetrahydrofuran at 30℃; for 23h;	A 70% B 16 % Spectr.

vinyl acetate (108-05-4) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) → 2'-O-(2-methoxyethyl)-5'-O-acetyl-5-methyluridine (1187056-81-0)

Conditions	Yield
With Novozyme 435 In 2-methyltetrahydrofuran at 20℃; for 5h; Molecular sieve; Enzymatic reaction; regioselective reaction;	70%

benzyl 2,7-dimethyl pixyl ether + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) → 5'-dimethylpixyl-2'-methoxyethylribothymidine

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 0.666667h; Molecular sieve; Inert atmosphere; regiospecific reaction;	70%

4,4'-dimethoxytrityl alcohol (40615-35-8) + 2'-O-(2-methoxyethyl)-5-methyluridine (163759-49-7) → 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridine (163759-50-0)

Conditions	Yield
With copper(II) nitrate In dichloromethane for 6h; Reagent/catalyst; Reflux; regioselective reaction;	70%

Upstream product

• 22423-26-3 O-2,2'-cyclo-5-methyluridine 
• 14983-42-7 tris(2-methoxyethyl)borate 
• 109-86-4 2-methoxy-ethanol 
• 854751-16-9 chloro-bis-(2-methoxy-phenyl)-phenyl-methane 
• 553664-34-9 3'-O-Acetyl-2'-O-(2-methoxyethyl)-5-methyl-5'-O-(4-phenylbenzoyl)uridin 
• 168427-88-1 1-[(2R,3R,4R,5R)-4-(2,4-Dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 1463-10-1 5-Methyluridine 
• 26879-47-0 1-(β-L-ribofuranosyl)thymine 
• 163759-50-0 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridine 
• 1392228-37-3 C₃₄H₃₅N₃O₁₀ 
• 1392228-36-2 C₃₈H₄₄N₂O₈ 
• 1392228-35-1 C₄₀H₄₀N₂O₈ 
• 1392228-34-0 C₃₄H₃₅BrN₂O₈ 
• 50-89-5 thymidine 

Downstream Products

• 163759-51-1 [5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridin-3'-O-yl]-2-cyanoethyl-N,N-diisopropylphosphoramidite 
• 125016-87-7 bis(4-methoxyphenyl)phenylmethyl methyl ether 
• 163759-50-0 5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(2-methoxyethyl)-5-methyluridine 
• 102343-05-5 3-(di-4-anisylphenylmethyl)-6-(di-4-anisylmethylene)-1,4-cyclohexadiene 
• 730979-84-7 triethylammonium 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-methoxyethyl)-5-methyluridine-3'-O-succinate 
• 1392228-34-0 C₃₄H₃₅BrN₂O₈ 
• 1392228-35-1 C₄₀H₄₀N₂O₈ 
• 1392228-36-2 C₃₈H₄₄N₂O₈ 
• 1392228-37-3 C₃₄H₃₅N₃O₁₀ 
• 182495-98-3 3'-O-acetyl-2'-O-methoxyethyl-5'-O-dimethoxytrityl-5-methyluridine 
• 163759-94-2 MOE 5-Me-C Amidite 
• 719302-87-1 C₅₇H₇₃N₅O₁₁Si₂ 
• 719302-98-4 C₄₆H₅₅N₅O₁₃ 
• 719302-83-7 2-[3-(tert-butyl-diphenyl-silanyloxy)-4-(2-methoxy-ethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-isoindole-1,3-dione 

Relevant articles and documents

Kilo-scale synthesis process for 2′-O-(2-methoxyethyl)-pyrimidine derivatives

We describe an improved process to produce 2′-O-(2-methoxyethyl)- pyrimidines. Starting with commercially available O-2,2′-anhydro-5- methyluridine and tris-(2-methoxyethyl)borate, we modified the ring-opening reaction conditions and changed to a continuous extraction purification method to give 2′-O-(2-methoxyethyl)-5-methyluridine. The dimethoxytritylation 5′/3′ ratios and yield were improved by the use of 2,6-lutidine as the base. Conditions to convert to the 5-methylcytidine analog and its isolation by crystallization were optimized. Final benzoylation was improved by developing a method to selectively hydrolyze benzoyl ester impurities. Copyright Taylor & Francis, Inc.

EFFECTS OF APOLIPOPROTEIN B INHIBITION ON GENE EXPRESSION PROFILES IN ANIMALS

Antisense compounds, compositions and methods are provided for modulating the expression of apolipoprotein B. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding apolipoprotein B. Methods of using these compounds for modulation of apolipoprotein B expression and for treatment of diseases associated with expression of apolipoprotein B are provided. Methods are provided for modulating the expression of genes involved in lipid metabolism, useful in the treatment of conditions associated with cardiovascular risk. Antisense oligonucleotides targeted to apolipoprotein B reduce the level of apolipoprotein B mRNA, lower serum cholesterol and shift liver gene expression profiles from those of an obese animal towards those of a lean animal. Further provided are methods for improving the cardiovascular risk of a subject through antisense inhibition of apolipoprotein B. Also provided are methods for employing antisense oligonucleotides targeted to apolipoprotein B to modulate a cellular pathway or metabolic process.

Antisense modulation of PTP1B expression

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