Dithymidine phosphate

Base Information

• Chemical Name: Dithymidine phosphate
• CAS No.: 1969-54-6
• Molecular Formula: C20H27 N4 O12 P
• Molecular Weight: 546.428
• DSSTox Substance ID: DTXSID701309371
• Nikkaji Number: J686.365E
• Wikidata: Q27145492
• ChEMBL ID: CHEMBL3608398
• Mol file: 1969-54-6.mol

Synonyms:d(TpT);d-TpT;dTpdT;thymidylyl (3',5')-ribothymidine;thymidylyl-(3'-5')-thymidine;Tp5meU

Chemical Property of Dithymidine phosphate

Chemical Property:

• Melting Point: 4.0 °C
• Boiling Point: °Cat760mmHg
• PKA: 1.37±0.50(Predicted)
• Flash Point: °C
• PSA: 234.21000
• Density: 1.586g/cm³
• LogP: -1.86600
• Storage Temp.: −20°C
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 8
• Exact Mass: 546.13630931
• Heavy Atom Count: 37
• Complexity: 1100

Purity/Quality:

99%, ^*data from raw suppliers

Thymidylyl-3?-5?-thymidineammoniumsalt ^*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)OC3CC(OC3CO)N4C=C(C(=O)NC4=O)C)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COP(=O)(O)O[C@H]3C[C@@H](O[C@@H]3CO)N4C=C(C(=O)NC4=O)C)O
• Uses: Thymidylyl-3''-5''-thymidine ammonium salt is used for skin photo-protection and repairs. A nucleoside.

Technology Process of Dithymidine phosphate

There total 16 articles about Dithymidine 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: 15.0%

2,2,2-trimethoxy-4,5-diphenyl-2,2-dihydro-1,3,2-dioxaphospholene (4850-55-9) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → thymidine 5'-(methyl hydrogenphosphate) (55728-65-9) + thymidylyl (3',5')thymidine (1969-54-6) + 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 2-oxo-1,2-diphenyl-ethyl ester

Guidance literature:

With pyridine; at 23 ℃; for 12h;

DOI:10.1080/00397919508015506

Reference yield: 6.2%

4-sulfanylphenol (637-89-8) + C26H31N4O12PS (1397776-03-2) → C26H31N4O13PS (1443257-89-3) + thymidylyl (3',5')thymidine (1969-54-6)

Guidance literature:

In water; for 0.0833333h; UV-irradiation; Inert atmosphere;

DOI:10.1002/anie.201209454

Reference yield:

deoxythymidylyl-(5'->3')-deoxythymidine-(Pin->N)-phenylalanine (68030-66-0,85647-52-5) → thymidine 3'-monophosphate (2642-43-5) + thymidine 5'-phosphate (365-07-1,15108-71-1,60363-32-8,96744-88-6,132696-16-3,143838-77-1) + deoxythymidylyl-(3'->N)-phenylalanine (68030-67-1,85699-72-5) + deoxythymidylyl-(5'->N)-phenylalanine (85590-79-0) + thymidylyl (3',5')thymidine (1969-54-6) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

With hydrogenchloride; water; at 37 ℃; for 1h; Product distribution; hydrolytic stability at various pH;

DOI:10.1007/BF00579428

upstream raw materials:

deoxythymidylyl-(5'->3')-deoxythymidine-(Pⁱⁿ->N)-phenylalanine

thymidine 3'-[thymidine 5'-(methyl phosphate)]

2,2,2-trimethoxy-4,5-diphenyl-2,2-dihydro-1,3,2-dioxaphospholene

thymidine

Downstream raw materials:

thymidine 5'-phosphate

thymidine

Refernces

• 1、 Wilk, Andrzej,Chmielewski, Marcin K.,Grajkowski, Andrzej,Phillips, Lawrence R.,Beaucage, Serge L.. "The 4-oxopentyl group as a labile phosphate/thiophosphate protecting group for synthetic oligodeoxyribonucleotides". . p. 5635 - 5639. Retrieved 2001.
• 2、 Lin, Gengjie,Li, Lei. "Oxidation and reduction of the 5-(2-Deoxyuridinyl)methyl radical". . p. 5594 - 5598. Retrieved 2013/06/27.