5-Hydroxy-5,6-dihydrothymidine

Base Information

• Chemical Name: 5-Hydroxy-5,6-dihydrothymidine
• CAS No.: 41308-58-1
• Molecular Formula: C₁₀H₁₆N₂O₆
• Molecular Weight: 260.247
• DSSTox Substance ID: DTXSID50961612
• Nikkaji Number: J488.538D
• Mol file: 41308-58-1.mol

Synonyms:5,6-dihydro-5-hydroxythymidine;5-hydroxy-5,6-dihydrothymidine;thymidine C5-hydrate;thymidine C5-hydrate, (5R)-isomer;thymidine C5-hydrate, (S)-isomer

Chemical Property of 5-Hydroxy-5,6-dihydrothymidine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: 1.522g/cm³
• LogP: 0.00000
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 260.10083623
• Heavy Atom Count: 18
• Complexity: 375

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CN(C(=O)NC1=O)C2CC(C(O2)CO)O)O
• Isomeric SMILES: CC1(CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)O)O

Technology Process of 5-Hydroxy-5,6-dihydrothymidine

There total 12 articles about 5-Hydroxy-5,6-dihydrothymidine 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: 94.0%

(5R)-3',5'-Bis-O-(tert-butyldimethylsilyl)-5,6-dihydro-5-hydroxythymidine (151936-96-8) → (+)-(5R)-5-hydroxy-5,6-dihydrothymidine (41308-58-1,67145-02-2,78216-58-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 8h; Ambient temperature;

DOI:10.1021/jo00074a057

Reference yield:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → N1-(2-deoxy-β-D-erythro-pentofuranosyl)-N3-tartronoylurea (32645-69-5) + cis-5,6-dihydroxy-5,6-dihydrothymidine (32645-65-1) + 3’-ketothymidine + 1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-hydroxy-5-methylhydantoin + trans-5,6-dihydroxy-5,6-dihydrothymidine + N-(2-deoxy-β-D-erythro-pentouranosyl)([2-hydroxypropanoyl]carbamoyl)carbamic acid + 2'-deoxy-5-(hydroxymethyl)uridine (5116-24-5,15425-01-1,143156-50-7) + (+)-(5R)-5-hydroxy-5,6-dihydrothymidine (41308-58-1,67145-02-2,78216-58-7) + (-)-(5S)-5-hydroxy-5,6-dihydrothymidine (67145-02-2) + thymin (65-71-4,28806-14-6,691841-57-3) + cis et trans 6-hydroxy-5,6-dihydrothymidine (68509-78-4) + 5,6-dihydrothymidine (5627-00-9) + N-(2-deoxy-β-D-erythro-pentofuranosyl)-5-hydroxy-5-methylbarbituric acid (38241-09-7) + 5-formyl-2'-deoxyuridine (4494-26-2)

Guidance literature:

at 25 ℃; for 0.5h; Sonication; Inert atmosphere;

DOI:10.1016/j.ultsonch.2015.05.016

Reference yield:

3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → (+)-(5R)-5-hydroxy-5,6-dihydrothymidine (41308-58-1,67145-02-2,78216-58-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 4 percent / bis-dihydroquinone phthalazine ligand, K₃Fe(CN)6, K₂CO₃, methanesulfonamide / potassium osmate dihydrate / 72 h / Ambient temperature

2: 81 percent / DMAP / tetrahydrofuran / -10 °C

3: 71 percent / N-methylcarbazole / tetrahydrofuran; H₂O / 5 h / Irradiation

4: 94 percent / TBAF / tetrahydrofuran / 8 h / Ambient temperature

With dmap; N-methylcarbazole; methanesulfonamide; bis-dihydroquinone phthalazine ligand; tetrabutyl ammonium fluoride; potassium carbonate; potassium hexacyanoferrate(III); potassium osmate(VI); In tetrahydrofuran; water;

DOI:10.1021/jo00074a057

upstream raw materials:

3-Trifluoromethyl-benzoic acid 5-hydroxy-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

(5R)-3',5'-Bis-O-(tert-butyldimethylsilyl)-5,6-dihydro-5-hydroxythymidine

thymidine

3',5'-O-di(tert-butyldimethylsilyl)thymidine

Downstream raw materials:

5'-benzoyl-5,6-dihydro-5-hydroxy-thymidine