[3-Hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl dihydrogen phosphate

Base Information

• Chemical Name: [3-Hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl dihydrogen phosphate
• CAS No.: 365-07-1
• Molecular Formula: C10H15N2O8P
• Molecular Weight: 322.211
• Hs Code.: HOSPHATE PRODUCT IDENTIFICATION
• NSC Number: 46713
• DSSTox Substance ID: DTXSID10861902
• Wikidata: Q105024006
• Mol file: 365-07-1.mol

Synonyms:Thymidine 5'MP;NSC-46713;thymidine 5'-monophos-phate;SCHEMBL16092807;DTXSID10861902;CHEBI:181566;NSC46713;[3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl dihydrogen phosphate;L001240;1-(2-Deoxy-5-O-phosphonopentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Chemical Property of [3-Hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl dihydrogen phosphate

Chemical Property:

• Appearance/Colour: white crystalline powder
• PKA: 1.86±0.10(Predicted)
• PSA: 160.89000
• Density: 1.654 g/cm³
• LogP: -1.39730
• Storage Temp.: −20°C
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 322.05660244
• Heavy Atom Count: 21
• Complexity: 529

Purity/Quality:

99%, ^*data from raw suppliers

TMP disodium salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)COP(=O)(O)O)O

Technology Process of [3-Hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl dihydrogen phosphate

There total 95 articles about [3-Hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-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: 82.0%

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → thymidine 5'-phosphate (365-07-1,15108-71-1,60363-32-8,96744-88-6,132696-16-3,143838-77-1)

Guidance literature:

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

DOI:10.1007/BF00598099

Reference yield:

C10H13N2O5Pol → thymidine 5'-phosphate (365-07-1,15108-71-1,60363-32-8,96744-88-6,132696-16-3,143838-77-1)

Guidance literature:

C₁₀H₁₃N₂O₅Pol; With 1H-tetrazole; C₆₀H₆₀NO₆P; In acetonitrile; for 0.1h; Succinyl Long Chain Alkylamine Controlled-Pore Glass

With pyridine; water; iodine; In tetrahydrofuran; for 0.5h; Succinyl Long Chain Alkylamine Controlled-Pore Glass

With ammonium hydroxide; In water; at 50 ℃; for 5h; Succinyl Long Chain Alkylamine Controlled-Pore Glass Reagent/catalyst;

DOI:10.1016/j.tetlet.2017.02.034

Reference yield:

NovaSynTM Tentagel resin-S-bound [2-(5-O-thymidine)-1,3,2-oxathiaphospholan-4-yl]methanethiol → thymidine 5'-phosphate (365-07-1,15108-71-1,60363-32-8,96744-88-6,132696-16-3,143838-77-1)

Guidance literature:

NovaSyn^TM Tentagel resin-S-bound [2-(5-O-thymidine)-1,3,2-oxathiaphospholan-4-yl]methanethiol; With tert.-butylhydroperoxide; In tetrahydrofuran; decane; at 20 ℃; for 1h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-Hydroxypropionitrile; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1021/ol050385w

upstream raw materials:

3'-O-acetylthymidine

[5']thymidylic acid monobenzyl ester

dibenzyl phosphochloridate

thymidine

Downstream raw materials:

methanol

thymidine

1-[(2R,4S,5R)-4-Hydroxy-5-(6-oxo-6,7-dihydro-5H-5,7-diaza-6λ⁵-phospha-dibenzo[a,c]cyclohepten-6-yloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

C₁₀H₁₆N₂O₁₀P₂

Refernces

• 1、 del Arco, Jon,Acosta, Javier,Pereira, Humberto M.,Perona, Almudena,Lokanath, Neratur K.,Kunishima, Naoki,Fernández-Lucas, Jesús. "Enzymatic Production of Non-Natural Nucleoside-5′-Monophosphates by a Thermostable Uracil Phosphoribosyltransferase". . p. 439 - 448. Retrieved 2017/12/13.
• 2、 Bou-Nader, Charles,Cornu, David,Guerineau, Vincent,Fogeron, Thibault,Fontecave, Marc,Hamdane, Djemel. "Enzyme Activation with a Synthetic Catalytic Co-enzyme Intermediate: Nucleotide Methylation by Flavoenzymes". supporting information. p. 12523 - 12527. Retrieved 2017/09/12.