Thymidine glycol

Base Information

• Chemical Name: Thymidine glycol
• CAS No.: 32645-65-1
• Molecular Formula: C10H16 N2 O7
• Molecular Weight: 276.246
• DSSTox Substance ID: DTXSID80954355
• Nikkaji Number: J488.537F
• Metabolomics Workbench ID: 49706
• Mol file: 32645-65-1.mol

Synonyms:5,6-dihydro-5,6-dihydroxythymidine;5,6-dihydroxy-5,6-dihydrothymidine;glycolthymidine;thymidine glycol;thymidine glycol, (5R*,6S*)-isomer;thymidine glycol, (5R,6R)-isomer;thymidine glycol, (5R,6S)-isomer;thymidine glycol, (5S,6R)-isomer;thymidine glycol, (5S,6S)-isomer;thymidine glycol, (cis)-isomer;thymidine glycol, (trans)-isomer

Chemical Property of Thymidine glycol

Chemical Property:

• PKA: 10.48±0.40(Predicted)
• PSA: 143.05000
• Density: 1.645g/cm³
• LogP: -2.71040
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 276.09575085
• Heavy Atom Count: 19
• Complexity: 403

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Thymidine glycol

There total 5 articles about Thymidine glycol 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:

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 + 5-formyl-5,6-dihydroxy-5,6-dihydro-2’-deoxyuridine + 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) + thymin (65-71-4,28806-14-6,691841-57-3) + 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:

With air; at 25 ℃; for 1h; Wavelength; Sonication;

DOI:10.1016/j.ultsonch.2015.05.016

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:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 2'-deoxy-5-(hydroxymethyl)uridine (5116-24-5,15425-01-1,143156-50-7) + cis(+) et cis(-) 5,6-dihydroxy-5,6-dihydrothymidine (32645-65-1,38645-22-6,38645-24-8,38709-52-3,38709-53-4,42957-13-1,42957-14-2,51268-80-5) + thymin (65-71-4,28806-14-6,691841-57-3) + 5,6-dihydroxy-5,6-dihydrothymidine (32645-65-1)

Guidance literature:

With potassium peroxomonosulfate; In water; at 75 ℃; for 4h; or in sodium phosphate buffer solution (pH 7.0);

upstream raw materials:

thymidine

(5R,6R)-trans-(+)-5-bromo-6-hydroxy-5,6-dihydrothymidine

Downstream raw materials:

thymidine

Refernces

• 1、 Berger, M.,Sarrazin, F.,Cadet, J.. "Reactions des radicaux 6-hydroxy-5,6-dihydrothymid-5-yles en solution aqueuse". . p. 853 - 862. Retrieved 2007/10/02.