Acetic acid (2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 185799-94-4
• Molecular Formula: C₂₀H₂₄N₂O₇
• Molecular Weight: 404.42
• Mol file: 185799-94-4.mol

Synonyms:

Chemical Property of Acetic acid (2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

There total 5 articles about Acetic acid (2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl 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:

Acetic acid (2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester → Acetic acid (2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (185799-94-4)

Guidance literature:

With pyridine; hydrogen fluoride; In dichloromethane; Yield given;

DOI:10.1016/S0040-4039(96)02005-9

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-3'-O-(t-butyldimethylsilyl)-2'-deoxythymidine (80971-33-1) → Acetic acid (2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (185799-94-4)

Guidance literature:

Multi-step reaction with 4 steps

1: diisopropylethylamine / CH₂Cl₂

2: CH₃SO₃H / methanol; CH₂Cl₂

3: TEA / CH₂Cl₂

4: 3M HF, pyridine / CH₂Cl₂

With pyridine; methanesulfonic acid; TEA; hydrogen fluoride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(96)02005-9

Reference yield:

5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) → Acetic acid (2R,3S,5R)-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (185799-94-4)

Guidance literature:

Multi-step reaction with 5 steps

1: imidazole / dimethylformamide

2: diisopropylethylamine / CH₂Cl₂

3: CH₃SO₃H / methanol; CH₂Cl₂

4: TEA / CH₂Cl₂

5: 3M HF, pyridine / CH₂Cl₂

With pyridine; 1H-imidazole; methanesulfonic acid; TEA; hydrogen fluoride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(96)02005-9

upstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-3'-O-(t-butyldimethylsilyl)-2'-deoxythymidine

5'-O-(4-4'-dimethoxytrityl)thymidine

3'-O-(tert-butyldimethylsilyl)-3-N-(benzyloxymethyl)thymidine