[(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate

Base Information

• Chemical Name: [(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
• CAS No.: 3715-64-8
• Molecular Formula: C10H15N2O7P
• Molecular Weight: 306.212

Synonyms:phosphoric acid mono-[cis-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl] ester;deoxythymidine-5'-phosphate;2',3'-dideoxythymidine-5'-monophosphate;NU-1603L D4TMP, L PACK;deoxythymidine monophosphate;deoxythymidine 5'-phosphate;

Chemical Property of [(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 140.66000
• Density: 1.547g/cm³
• LogP: -0.36810

Purity/Quality:

≥ 95% by HPLC ^*data from raw suppliers

3`-Deoxy-5`-thymidylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3`-Deoxy-5`-thymidylic Acid has been shown to complex with human thymidylate kinase via hydrogen bonding between Arg97 residues and phosphate groups. This interaction leads to the closed P-loop conformation in human thymidylate kinase, which promotes phosphorylation of nucleotides and has the potential as a model for novel compounds as a result of structure-based design studies.

Technology Process of [(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate

There total 9 articles about [(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate 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: 78.0%

3'-Deoxythymidine (3416-05-5) → [14C]-Deoxythymidine monophosphate (3715-64-8)

Guidance literature:

With tris(p-nitrophenyl)phosphate; at 50 ℃; Erwina herbicola 47/3 cells;

DOI:10.1007/BF00598099

Reference yield:

1-[(2R,5S)-5-(6-Chloro-2-oxo-4H-2λ5-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione → 4-chloro-2-hydroxymethylphenol (5330-38-1) + [14C]-Deoxythymidine monophosphate (3715-64-8)

Guidance literature:

With water; at 37 ℃; pH=7.5; hydrolyse stability (t_1/2);

Reference yield:

5-Methyl-1-[(2R,5S)-5-(2-oxo-4H-2λ5-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione → salicylic alcohol (90-01-7) + [14C]-Deoxythymidine monophosphate (3715-64-8)

Guidance literature:

With water; at 37 ℃; pH=7.5; hydrolyse stability (t_1/2);

upstream raw materials:

3'-Deoxythymidine

1-(D,L-5-hydroxymethyl-2-tetrahydrofuryl)-5-methyluracil

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