3'-(Trityl)amino-3'-deoxythymidine

Base Information

• Chemical Name: 3'-(Trityl)amino-3'-deoxythymidine
• CAS No.: 195375-41-8
• Molecular Formula: C29H29N3O4
• Molecular Weight: 483.567
• DSSTox Substance ID: DTXSID40470344
• Nikkaji Number: J2.325.441G
• Wikidata: Q82298413
• Mol file: 195375-41-8.mol

Synonyms:3'-(trityl)amino-3'-deoxythymidine;SCHEMBL5491393;DTXSID40470344;FFQYKVHJPYQWER-JIMJEQGWSA-N;1-[(2R,4S,5S)-5-(hydroxymethyl)-4-(tritylamino)oxolan-2-yl]-5-methylpyrimidine-2,4-dione;1-((2R,4S,5S)-5-(Hydroxymethyl)-4-(tritylamino)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Chemical Property of 3'-(Trityl)amino-3'-deoxythymidine

Chemical Property:

• XLogP3: 4.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 483.21580641
• Heavy Atom Count: 36
• Complexity: 766

Purity/Quality:

97% ^*data from raw 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)CO)NC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)NC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5

Technology Process of 3'-(Trityl)amino-3'-deoxythymidine

There total 7 articles about 3'-(Trityl)amino-3'-deoxythymidine 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: 95.0%

trityl chloride (76-83-5) + 3'-amino-3'-deoxythymidine (52450-18-7) → 1-[(2R,4S,5S)-5-Hydroxymethyl-4-(trityl-amino)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (195375-41-8)

Guidance literature:

With pyridine; triethylamine;

DOI:10.1081/NCN-200060068

Reference yield: 90.0%

4-Methoxy-benzoic acid (2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(trityl-amino)-tetrahydro-furan-2-ylmethyl ester (195375-40-7) → 1-[(2R,4S,5S)-5-Hydroxymethyl-4-(trityl-amino)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (195375-41-8)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; methanol; for 1.5h; Ambient temperature;

DOI:10.1021/jo970801t

Reference yield: 85.0%

trityl chloride (76-83-5) → 1-[(2R,4S,5S)-5-Hydroxymethyl-4-(trityl-amino)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (195375-41-8)

Guidance literature:

3'-amino-3'-deoxythymidine; With pyridine; N-ethyl-N,N-diisopropylamine; for 0.166667h;

trityl chloride; at 20 - 50 ℃;

upstream raw materials:

4-Methoxy-benzoic acid (2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(trityl-amino)-tetrahydro-furan-2-ylmethyl ester

trityl chloride

3'-amino-3'-deoxythymidine

3'-Azido-5'-O-(4-methoxybenzoyl)-3'-deoxythymidine

Downstream raw materials:

3'-NH-trityl-3'-aminothymidine 5'-O-cyanoethyl-N,N-diisopropylaminophosphoramidite

(1'R, 3'S, 4'S)-3'-deoxy-3'-tritylaminothymidine-4'-carboxylic acid

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