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

Base Information

• Chemical Name: 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
• CAS No.: 72718-44-6
• Molecular Formula: C₄₂H₄₅N₄O₁₃P
• Molecular Weight: 844.812
• Mol file: 72718-44-6.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 2 articles about 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 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: 62.0%

methanol (67-56-1) + C12H15N2O9P(2-) (126575-08-4) + 4-Hydroxy-1-((2R,4S,5R)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidin-2-one (7791-71-1) → 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)

Guidance literature:

With 2,4,6-triisopropylbenzenesulfonyl tetrazolide;

Reference yield:

5'-O-tritylthymidine (7791-71-1) → 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 (72718-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran; pyridine / -70 °C

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

In tetrahydrofuran; pyridine;

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

Reference yield: 92.0%

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) → Acetic acid (2R,3S,5R)-2-{hydroxy-[(2R,3S,5R)-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yloxy]-phosphoryloxymethyl}-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (37668-78-3)

Guidance literature:

With triethylamine; para-thiocresol; In 1,4-dioxane; at 20 ℃; for 4h;

upstream raw materials:

5'-O-tritylthymidine

methanol

C₁₂H₁₅N₂O₉P^(2-)

4-Hydroxy-1-((2R,4S,5R)-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidin-2-one

Downstream raw materials:

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

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

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