5'O-trityl-2',3'-dideoxy-2',3'-didehydrouridine

Base Information

• Chemical Name: 5'O-trityl-2',3'-dideoxy-2',3'-didehydrouridine
• CAS No.: 6038-55-7
• Molecular Formula: C28H24N2O4
• Molecular Weight: 452.51
• DSSTox Substance ID: DTXSID10454858
• Nikkaji Number: J774.708J
• Wikidata: Q82276640
• ChEMBL ID: CHEMBL1807019
• Mol file: 6038-55-7.mol

Synonyms:CHEMBL1807019;6038-55-7;5'O-trityl-2',3'-dideoxy-2',3'-didehydrouridine;SCHEMBL8541641;DTXSID10454858;FNGKTILOSNGWLS-AZGAKELHSA-N;BDBM50348776;1-[(2R,5S)-5-(trityloxymethyl)-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione;5'-O-Trityl-2',3'-dideoxy-2',3'-didehydrouridine

Chemical Property of 5'O-trityl-2',3'-dideoxy-2',3'-didehydrouridine

Chemical Property:

• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 452.17360725
• Heavy Atom Count: 34
• Complexity: 730

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)OCC4C=CC(O4)N5C=CC(=O)NC5=O
• Isomeric SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC[C@@H]4C=C[C@@H](O4)N5C=CC(=O)NC5=O

Technology Process of 5'O-trityl-2',3'-dideoxy-2',3'-didehydrouridine

There total 20 articles about 5'O-trityl-2',3'-dideoxy-2',3'-didehydrouridine 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: 99.0%

1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione (110524-37-3) → 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)uracil (6038-55-7)

Guidance literature:

With tellurium; lithium triethylborohydride; In tetrahydrofuran; acetonitrile; for 16h; Ambient temperature; further reagents and solvents: Li₂Te, Na₂Se, Na₂Te, dioxane;

DOI:10.1021/jo9610570

Reference yield: 91.0%

2'-chloro-2'-deoxy-3'-O-phenoxythiocarbonyl-5'-O-trityluridine → 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)uracil (6038-55-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 60 - 70 ℃; for 4h;

DOI:10.1016/S0040-4039(00)97480-X

Reference yield: 70.0%

Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-4-chloro-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl] ester (130718-57-9) → 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)uracil (6038-55-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 60 - 70 ℃;

DOI:10.1016/S0040-4039(00)97480-X

upstream raw materials:

Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-4-chloro-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl] ester

1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione

1-(2,3-O-thiocarbonyl-5-O-tritylribofuranosyl)uracil

5'-O-(triphenylmethyl)uridine 2',3'-bis(p-toluenesulfonate)

Refernces

• 1、 Takamatsu, Satoshi,Katayama, Satoshi,Hirose, Naoko,De Cock, Etienne,Schelkens, Geert,Demillequand, Marc,Brepoels, Jozef,Izawa, Kunisuke. "Convenient synthesis of fluorinated nucleosides with perfluoroalkanesulfonyl fluorides". . p. 849 - 861. Retrieved 2007/10/03.
• 2、 Clive, Derrick L.J.,Sgarbi, Paulo W.M.,Wickens, Philip L.. "Synthesis of 2′,3′-Didehydro-2′,3′-dideoxynucleosides by Reaction of 5′-O-Protected Nucleoside 2′,3′-Dimesylates with Lithium Areneselenolates". . p. 3751 - 3753. Retrieved 2007/10/03.