Methoxy-acetic acid (2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(bis-benzyloxy-phosphoryloxymethoxymethyl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Methoxy-acetic acid (2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(bis-benzyloxy-phosphoryloxymethoxymethyl)-tetrahydro-furan-3-yl ester
• CAS No.: 133510-66-4
• Molecular Formula: C₃₅H₃₇N₂O₁₂P
• Molecular Weight: 708.659
• Mol file: 133510-66-4.mol

Synonyms:

Chemical Property of Methoxy-acetic acid (2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(bis-benzyloxy-phosphoryloxymethoxymethyl)-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methoxy-acetic acid (2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(bis-benzyloxy-phosphoryloxymethoxymethyl)-tetrahydro-furan-3-yl ester

There total 6 articles about Methoxy-acetic acid (2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(bis-benzyloxy-phosphoryloxymethoxymethyl)-tetrahydro-furan-3-yl ester 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:

3'-O-methoxyacetyl-N3-benzoyl-thymidine (130867-61-7) → Methoxy-acetic acid (2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(bis-benzyloxy-phosphoryloxymethoxymethyl)-tetrahydro-furan-3-yl ester (133510-66-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / benzoyl peroxide / acetonitrile / 2 h / Ambient temperature

2: N-iodosuccinimide (NIS), molecular sieves (5 Angstroem) / 1,2-dichloro-ethane; tetrahydrofuran / 0.33 h / Ambient temperature

With N-iodo-succinimide; 5A molecular sieve; dibenzoyl peroxide; In tetrahydrofuran; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0040-4020(01)86429-2

Reference yield:

5’-O-dimethoxytrityl-3’-O-methoxyacetylthymidine (130867-57-1) → Methoxy-acetic acid (2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(bis-benzyloxy-phosphoryloxymethoxymethyl)-tetrahydro-furan-3-yl ester (133510-66-4)

Guidance literature:

Multi-step reaction with 4 steps

1: N,N-diisopropylethylamine (DIPEA) / pyridine / 1 h / Ambient temperature

2: 85 percent / 90percent aq. acetic acid / 0.5 h / 50 °C

3: 72 percent / benzoyl peroxide / acetonitrile / 2 h / Ambient temperature

4: N-iodosuccinimide (NIS), molecular sieves (5 Angstroem) / 1,2-dichloro-ethane; tetrahydrofuran / 0.33 h / Ambient temperature

With N-iodo-succinimide; 5A molecular sieve; acetic acid; N-ethyl-N,N-diisopropylamine; dibenzoyl peroxide; In tetrahydrofuran; pyridine; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0040-4020(01)86429-2

Reference yield:

Methoxy-acetic acid (2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester (130867-58-2) → Methoxy-acetic acid (2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(bis-benzyloxy-phosphoryloxymethoxymethyl)-tetrahydro-furan-3-yl ester (133510-66-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / 90percent aq. acetic acid / 0.5 h / 50 °C

2: 72 percent / benzoyl peroxide / acetonitrile / 2 h / Ambient temperature

3: N-iodosuccinimide (NIS), molecular sieves (5 Angstroem) / 1,2-dichloro-ethane; tetrahydrofuran / 0.33 h / Ambient temperature

With N-iodo-succinimide; 5A molecular sieve; acetic acid; dibenzoyl peroxide; In tetrahydrofuran; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0040-4020(01)86429-2

upstream raw materials:

phosphoric acid dibenzyl ester

5'-O-methylthiomethyl-3'-O-methoxyacetyl-N³-benzoyl-thymidine

3'-O-methoxyacetyl-N³-benzoyl-thymidine

5’-O-dimethoxytrityl-3’-O-methoxyacetylthymidine