Phosphoric acid (2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester methyl ester

Base Information

• Chemical Name: Phosphoric acid (2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester methyl ester
• CAS No.: 88459-53-4
• Molecular Formula: C₄₀H₄₃N₄O₁₂P
• Molecular Weight: 802.775
• Mol file: 88459-53-4.mol

Synonyms:

Chemical Property of Phosphoric acid (2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphoric acid (2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester methyl ester

There total 8 articles about Phosphoric acid (2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester methyl 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-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-{[(2R,3S,5R)-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yloxy]-methoxy-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester (72718-44-6) → Phosphoric acid (2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester methyl ester (88459-53-4)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; ethanol; at 20 ℃; for 0.116667h; Yield given;

Reference yield:

5'-O-tritylthymidine (7791-71-1) → Phosphoric acid (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester methyl ester (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester (88459-53-4)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran; pyridine / -70 °C

2: 1. -70 deg C, THF, pyridine 2. oxidation with iodine

3: MeOH, NH₃

With methanol; ammonia; In tetrahydrofuran; pyridine;

DOI:10.1016/0040-4039(81)80135-9

Reference yield:

4-Hydroxy-1-((2R,4S,5R)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidin-2-one (7791-71-1) → Phosphoric acid (2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester methyl ester (88459-53-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / 2,4,6-triisopropylbenzenesulfonyltetrazolide

2: 1 M aq. NaOH / ethanol; dioxane / 0.12 h / 20 °C

With sodium hydroxide; 2,4,6-triisopropylbenzenesulfonyl tetrazolide; In 1,4-dioxane; ethanol;

upstream raw materials:

Acetic acid (2R,3S,5R)-2-{methoxy-[(2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yloxy]-phosphoryloxymethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

5'-O-tritylthymidine

Acetic acid (2R,3S,5R)-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-{[(2R,3S,5R)-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yloxy]-methoxy-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester

C₁₂H₁₅N₂O₉P^(2-)