1-(2-deoxy-5-O-trityl-beta-D-threopentofuranosyl)thymine

Base Information

• Chemical Name: 1-(2-deoxy-5-O-trityl-beta-D-threopentofuranosyl)thymine
• CAS No.: 55612-11-8
• Molecular Formula: C29H28N2O5
• Molecular Weight: 484.552
• European Community (EC) Number: 407-120-6,633-500-8
• ChEMBL ID: CHEMBL4513515
• DSSTox Substance ID: DTXSID60970952
• Nikkaji Number: J1.607.817D
• Wikidata: Q76421984
• Mol file: 55612-11-8.mol

Synonyms:55612-11-8;1-((2R,4R,5R)-4-hydroxy-5-(trityloxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione;1-((2R,4R,5R)-4-Hydroxy-5-((trityloxy)methyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione;1-[(2R,4R,5R)-4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione;1-(2-deoxy-5-O-trityl-beta-D-threopentofuranosyl)thymine;FZDHVUVGQXVYOP-TWJOJJKGSA-N;7791-71-1;5'-O-Trityl-3'-b-hydroxythymidine;EC 407-120-6;SCHEMBL6077816;CHEMBL4513515;DTXSID60970952;5'-O-Trityl-3'-?-hydroxythymidine;AKOS025402421;AC-8905;5'-O-Trityl-3'- beta -hydroxythymidine;1-(5-O-trityl-2-deoxy-beta-D-lyxofuranosyl)thymine;W-203789;5-O-TRITYL-2-DEOXY-BETA-D-LYXOFURANOSYLTHYMINE;5'-O-Trityl-2'-deoxy-beta-D-lyxofuranosylthymine, 98%;1-(2-Deoxy-5-O-trityl-beta-D-threo-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione

Chemical Property of 1-(2-deoxy-5-O-trityl-beta-D-threopentofuranosyl)thymine

Chemical Property:

• Melting Point: 246-248 °C(lit.)
• Refractive Index: 1.62
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 93.55000
• Density: 1.275g/cm³
• LogP: 3.50210
• Solubility.: Chloroform, Dichloromethane, Methanol
• 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:

99.9% ^*data from raw suppliers

5’-O-Trityl-3’-β-hydroxythymidine ^*data from reagent suppliers

Safty Information:

• Statements: 53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

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
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@H]([C@H](O2)COC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)O

Technology Process of 1-(2-deoxy-5-O-trityl-beta-D-threopentofuranosyl)thymine

There total 35 articles about 1-(2-deoxy-5-O-trityl-beta-D-threopentofuranosyl)thymine 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: 89.0%

3'-Tosyl-5'-O-trityl thymidine (141690-73-5) → 5'-O-trityldeoxyxylothymidine (55612-11-8)

Guidance literature:

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

DOI:10.1016/S0022-1139(00)82356-8

Reference yield: 67.0%

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine (42214-24-4) → 5'-O-trityldeoxyxylothymidine (55612-11-8)

Guidance literature:

With water; sodium hydroxide; In ethanol; for 2h; Reflux;

DOI:10.1021/jm100803c

Reference yield: 60.0%

2-((2R,3R)-5-Benzyloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy)-5-methyl-3H-pyrimidin-4-one (188559-35-5) → 5'-O-trityldeoxyxylothymidine (55612-11-8)

Guidance literature:

With pyridine hydrogenfluoride; In 1,4-dioxane;

DOI:10.1016/S0040-4039(96)02520-8

upstream raw materials:

5'-O-trityl-2,3'-anhydrothymidine

diphenyl diselenide

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine

3'-Tosyl-5'-O-trityl thymidine

Downstream raw materials:

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine

1-(3'-C-cyano-2',3'-dideoxy-β-D-erythro-pentofuranosyl)thymine

stavudin

3'-Fluoro-5'-O-trityl-deoxythymidine

Refernces

• 1、 Srivastav, Naveen C.,Shakya, Neeraj,Mak, Michelle,Agrawal, Babita,Tyrrell, D. Lorne,Kumar, Rakesh. "Antiviral activity of various 1-(2′-Deoxy-β- d -lyxofuranosyl), 1-(2′-Fluoro-β- d -xylofuranosyl), 1-(3′-Fluoro-β- d -arabinofuranosyl), and 2′-fluoro-2′,3′-didehydro-2′, 3′-dideoxyribose pyrimidine nucleoside analogues against duck hepatitis B virus (DHBV) and human hepatitis B virus (HBV) replication". experimental part. p. 7156 - 7166. Retrieved 2010/12/19.
• 2、 Kumar, Piyush,Ohkura, Kazue,Balzarini, Jan,De Clercq, Erik,Seki, Koh-Ichi,Wiebe, Leonard I.. "Synthesis and Antiviral Activity of Novel Fluorinated 2′,3′ -Dideoxynucleosides". . p. 7 - 29. Retrieved 2007/10/03.