Thymidine, 5'-O-(triphenylmethyl)-

Base Information

• Chemical Name: Thymidine, 5'-O-(triphenylmethyl)-
• CAS No.: 7791-71-1
• Molecular Formula: C29H28N2O5
• Molecular Weight: 484.552
• NSC Number: 75113
• DSSTox Substance ID: DTXSID40864128
• Mol file: 7791-71-1.mol

Synonyms:7791-71-1;Thymidine, 5'-O-(triphenylmethyl)-;1-[4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione;Thymidine, trityl deriv;MFCD00038462;Monotritylthymidine;1-(2-deoxy-5-O-trityl-beta-D-threopentofuranosyl)thymine;CHEMBL336109;SCHEMBL1727320;DTXSID40864128;NSC75113;BDBM50118489;NSC 75113;NSC-75113;AKOS015913528;PD128925;SY113011;FT-0653416;FT-0675689;5 inverted exclamation mark -O-tritylthymidine;1-(4-Hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione;1-[2-Deoxy-5-O-(triphenylmethyl)pentofuranosyl]-5-methylpyrimidine-2,4(1H,3H)-dione

Chemical Property of Thymidine, 5'-O-(triphenylmethyl)-

Chemical Property:

• Melting Point: 125 °C(Solv: acetone (67-64-1); ethyl ether (60-29-7))
• PKA: 9.55±0.10(Predicted)
• PSA: 93.55000
• Density: 1.275g/cm³
• LogP: 3.50210
• Storage Temp.: −20°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 484.19982200
• Heavy Atom Count: 36
• Complexity: 765

Purity/Quality:

99% ^*data from raw suppliers

5?-O-Tritylthymidine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)COC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)O

Technology Process of Thymidine, 5'-O-(triphenylmethyl)-

There total 22 articles about Thymidine, 5'-O-(triphenylmethyl)- 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: 100.0%

3'-O-(2-hydroxy)ethoxycarbonyl-5'-O-tritylthymidine (79258-32-5) → 5'-O-tritylthymidine (7791-71-1)

Guidance literature:

With ammonia; In 1,4-dioxane; water; for 0.25h; Ambient temperature;

DOI:10.1016/S0040-4039(01)90482-4

Reference yield: 97.1%

trityl chloride (76-83-5) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 5'-O-tritylthymidine (7791-71-1)

Guidance literature:

With pyridine; at 20 ℃; for 21.5h;

Reference yield: 95.0%

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine (42214-24-4) → 5'-O-tritylthymidine (7791-71-1)

Guidance literature:

With sodium hydroxide; In ethanol; for 1h; Heating;

DOI:10.1021/jm00055a009

upstream raw materials:

trityl chloride

thymidine

3'-O-(2-hydroxy)ethoxycarbonyl-5'-O-tritylthymidine

3'-O-TCBOC-5'-O-tritylthymidin

Downstream raw materials:

thymidylyl-(5'->3')-O^5'-trityl-thymidine

thymidine 3'-O-(4-nitrophenyl)phosphate

3'-O-acetyl-5'-O-triphenylmethylthymidine

3'-O-benzyl-2'-deoxythymidine

Refernces

• 1、 Lehnhoff,Karl,Ugi. "The cleavage of the 2,2,2-trichloro-1,1-dimethylethoxycarbonyl protective group by tin(II) tris(benzenethiolate)". . p. 309 - 310. Retrieved 1991.
• 2、 Arzel, Laurence,Dubreuil, Didier,Dénès, Fabrice,Silvestre, Virginie,Mathé-Allainmat, Monique,Lebreton, Jacques. "Synthesis of Ribonucleosidic Dimers with an Amide Linkage from D-Xylose". . p. 10742 - 10758. Retrieved 2016/11/29.
• 3、 Saudi, Milind,Zmurko, Joanna,Kaptein, Suzanne,Rozenski, Jef,Neyts, Johan,Van Aerschot, Arthur. "In search of Flavivirus inhibitors part 2: Tritylated, diphenylmethylated and other alkylated nucleoside analogues". . p. 98 - 109. Retrieved 2014/03/21.