5'-O-(4,4'-Dimethoxytrityl)thymidine

Base Information

• Chemical Name: 5'-O-(4,4'-Dimethoxytrityl)thymidine
• CAS No.: 40615-39-2
• Deprecated CAS: 138799-00-5,169474-07-1,203926-33-4,1093730-81-4,1093730-81-4,169474-07-1,203926-33-4
• Molecular Formula: C31H32N2O7
• Molecular Weight: 544.604
• Hs Code.: 29349990
• European Community (EC) Number: 255-003-1
• DSSTox Substance ID: DTXSID1074961
• Nikkaji Number: J236.252J
• Wikidata: Q72468680
• ChEMBL ID: CHEMBL3143147
• Mol file: 40615-39-2.mol

Synonyms:5'-O-dimethoxytritylthymidine;5'-O-dimethyltritylthymidine;5-DMTT

Chemical Property of 5'-O-(4,4'-Dimethoxytrityl)thymidine

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0Pa at 20℃
• Melting Point: 114-116 °C (subl.)(lit.)
• Refractive Index: 7 ° (C=1, MeOH)
• Boiling Point: 618.41°C (rough estimate)
• PKA: 9.55±0.10(Predicted)
• PSA: 112.01000
• Density: 1.272 g/cm³
• LogP: 3.51930
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 3mg/L at 20℃
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 544.22095136
• Heavy Atom Count: 40
• Complexity: 879

Purity/Quality:

98%, ^*data from raw suppliers

5’-O-(4,4’-Dimethoxytrityl)thymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)O
• Uses: 5'-O-(4,4'-Dimethoxytrityl)thymidine is used in the solid-phase synthesis of polynucleotides and polythymidylic acids by the block coupling phosphotriester method. Further, it is used in the stereoselective synthesis of 3'-deoxy-3'-threo-hydroxymethyl nucleoside. In addition to this, it is used as a research tool for antiviral and anticancer studies.

Technology Process of 5'-O-(4,4'-Dimethoxytrityl)thymidine

There total 63 articles about 5'-O-(4,4'-Dimethoxytrityl)thymidine 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: 97.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 5h;

DOI:10.1055/s-2006-933147

Reference yield: 96.0%

2-Azidomethyl-benzoic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (289712-59-0) → 5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2)

Guidance literature:

With diphenyl(methyl)phosphine; In 1,4-dioxane; water; at 20 ℃; for 0.25h; Further Variations:; Catalysts; Reaction partners; Reagents; Solvents; reaction times; Product distribution;

DOI:10.1016/S0040-4039(00)02183-3

Reference yield: 93.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) + 3'-O-(4,4'-dimethoxytriphenylmethyl)-5'-O-fluorenylmethoxycarbonylthymidine (52417-09-1)

Guidance literature:

With pyridine; at 20 ℃; for 1.5h;

DOI:10.1080/15257770600726059

upstream raw materials:

C₄₆H₅₅N₄O₁₄P

3'-O-(4,4'-dimethoxytrityl)thymidin-5'-yl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl ethyl phosphonate

C₄₂H₄₇N₄O₁₄P

ethanolamine

Downstream raw materials:

5’-O-(4,4’-dimethoxytriphenylmethyl)thymidine-3’-O-succinate

Phosphoric acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2,6-dichloro-phenyl ester 2-pyridin-2-yl-ethyl ester

Phthalic acid mono-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester

C₄₃H₅₀N₃O₇PS