2-((2R,3R)-5-Benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-5-methyl-3H-pyrimidin-4-one

Base Information

• Chemical Name: 2-((2R,3R)-5-Benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-5-methyl-3H-pyrimidin-4-one
• CAS No.: 188559-35-5
• Molecular Formula: C₃₆H₃₄N₂O₅
• Molecular Weight: 574.676
• Mol file: 188559-35-5.mol

Synonyms:2-((2R,3R)-5-Benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-5-methyl-3H-pyrimidin-4-one

Chemical Property of 2-((2R,3R)-5-Benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-5-methyl-3H-pyrimidin-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2R,3R)-5-Benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-5-methyl-3H-pyrimidin-4-one

There total 11 articles about 2-((2R,3R)-5-Benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-5-methyl-3H-pyrimidin-4-one 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: 63.0%

4-Allyloxy-2-((2R,3R)-5-benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-5-methyl-pyrimidine (188559-30-0) → 2-((2R,3R)-5-Benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-5-methyl-3H-pyrimidin-4-one (188559-35-5)

Guidance literature:

With pyridine; Wilkinson's catalyst; In ethanol; for 5h; Heating;

DOI:10.1016/S0040-4039(96)02520-8

Reference yield:

2,6-dichloro-5-methylpyrimidine (1780-31-0) → 2-((2R,3R)-5-Benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-5-methyl-3H-pyrimidin-4-one (188559-35-5)

Guidance literature:

Multi-step reaction with 3 steps

1: Na

2: 70 percent / NaH / dimethylformamide

3: 63 percent / Rh(PPh₃)3Cl, pyridine / aq. ethanol / 5 h / Heating

With pyridine; Wilkinson's catalyst; sodium; sodium hydride; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(96)02520-8

Reference yield:

5,5-Dibenzyloxy-2E-penten-1-ol (134485-31-7) → 2-((2R,3R)-5-Benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-5-methyl-3H-pyrimidin-4-one (188559-35-5)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N, DMAP

2: K₂OsO₄*2H₂O, K₃Fe(CN)6, K₂CO₃, DHQD-PHN / H₂O; 2-methyl-propan-2-ol

3: H₂SO₄ / tetrahydrofuran / 0 °C

4: 70 percent / NaH / dimethylformamide

5: 63 percent / Rh(PPh₃)3Cl, pyridine / aq. ethanol / 5 h / Heating

With pyridine; dmap; potassium osmate(VI); Wilkinson's catalyst; sulfuric acid; sodium hydride; potassium carbonate; 9-O-(9'-phenanthryl) ether of dihydroquinidine; triethylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0040-4039(96)02520-8

upstream raw materials:

4-Allyloxy-2-((2R,3R)-5-benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-5-methyl-pyrimidine

2,6-dichloro-5-methylpyrimidine

5,5-Dibenzyloxy-2E-penten-1-ol

3,3-dibenzyloxypropanal

Downstream raw materials:

5'-O-trityl-O²,3'-cycloanhydro-N³-thymidine

5'-O-trityldeoxyxylothymidine

threothymidine