Thymidine, 5'-o-(p-toluenesulfonyl)-

Base Information

• Chemical Name: Thymidine, 5'-o-(p-toluenesulfonyl)-
• CAS No.: 7253-19-2
• Molecular Formula: C17H20 N2 O7 S
• Molecular Weight: 396.421
• NSC Number: 69443
• DSSTox Substance ID: DTXSID10993373
• Mol file: 7253-19-2.mol

Synonyms:Thymidine, 5'-o-(p-toluenesulfonyl)-;Thymidine, 5'-(4-methylbenzenesulfonate);7253-19-2;5'-O-Tosylthymidine;[3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzenesulfonate;NSC 69443;BRN 0632553;NSC69443;DTXSID10993373;NSC-69443;FT-0675340;SR-01000359272;WLN: T6NVMVJ E1 A- BT5OTJ DQ E1SWR D1;SR-01000359272-1;1-[2-Deoxy-5-O-(4-methylbenzene-1-sulfonyl)pentofuranosyl]-4-hydroxy-5-methylpyrimidin-2(1H)-one

Chemical Property of Thymidine, 5'-o-(p-toluenesulfonyl)-

Chemical Property:

• Melting Point: >161°C (dec.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 136.07000
• Density: 1.425 g/cm³
• LogP: 1.28810
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 396.09912215
• Heavy Atom Count: 27
• Complexity: 722

Purity/Quality:

97% ^*data from raw suppliers

5’-TosylThymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2C(CC(O2)N3C=C(C(=O)NC3=O)C)O
• Uses: A nucleoside analogue as inhibitors of thymidylate kinases A nucleoside analogue as inhibitors of thymidylate kinases.

Technology Process of Thymidine, 5'-o-(p-toluenesulfonyl)-

There total 9 articles about Thymidine, 5'-o-(p-toluenesulfonyl)- 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: 66.0%

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 5'-O-(p-toluenesulfonyl)thymidine (7253-19-2)

Guidance literature:

DOI:10.1002/hlca.200490252

Reference yield:

3'-O-(tert-butyldimethylsilyl)-5'-O-(p-toluenesulfonyl)thymidine (129801-99-6) → 5'-O-(p-toluenesulfonyl)thymidine (7253-19-2)

Guidance literature:

With hydrogenchloride; In acetonitrile; for 6h; Yield given;

DOI:10.1021/jo00385a026

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → 5'-O-(p-toluenesulfonyl)thymidine (7253-19-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-(N,N-dimethylamino)pyridine 4-DMAP / CH₂Cl₂ / 6 h

2: aq. HCl / acetonitrile / 6 h

With hydrogenchloride; dmap; In dichloromethane; acetonitrile;

DOI:10.1021/jo00385a026

upstream raw materials:

3'-O-(tert-butyldimethylsilyl)-5'-O-(p-toluenesulfonyl)thymidine

thymidine

p-toluenesulfonyl chloride

3'-O-(t-butyldimethylsilyl)thymidine

Downstream raw materials:

2,3'-anhydro-1-<2-deoxy-5-O-(p-tolylsulfonyl)-β-D-threo-pentofuranosyl>thymine

1-((2R,4S,5R)-4-Hydroxy-5-{4-[(1Z,4Z,9Z,15Z)-15-(4-hydroxy-phenyl)-10,20-di-p-tolyl-porphyrin-5-yl]-phenoxymethyl}-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

C₆₆H₅₈N₈O₁₀

C₆₆H₅₈N₈O₁₀