43179-28-8

Basic information

• Product Name: thymidine bromohydrin
• Synonyms: thymidine bromohydrin
• CAS NO: 43179-28-8
• Molecular Formula: C₁₀H₁₅BrN₂O₆
• Molecular Weight: 339.1399
• Mol File: 43179-28-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.83g/cm³
• Refractive Index: 1.625
• CAS DataBase Reference: thymidine bromohydrin(CAS DataBase Reference)
• NIST Chemistry Reference: thymidine bromohydrin(43179-28-8)
• EPA Substance Registry System: thymidine bromohydrin(43179-28-8)

Safety Data

• Hazardous Substances Data: 43179-28-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H15BrN2O6/c1-10(11)7(16)12-9(18)13(8(10)17)6-2-4(15)5(3-14)19-6/h4-6,8,14-15,17H,2-3H2,1H3,(H,12,16,18)/t4-,5+,6+,8-,10+/m0/s1

Upstream product

• 50-89-5 thymidine 

Downstream Products

• 5116-24-5 2'-deoxy-5-(hydroxymethyl)uridine 
• 107908-74-7 (5R,6R)-cis-(+)-6-anilino-5-hydroxy-5,6-dihydrothymidine 
• 107908-74-7 (5R,6S)-trans-(+)-6-anilino-5-hydroxy-5,6-dihydrothymidine 
• 107908-77-0 ethyl N-<(5R,6S)-trans-(+)-5-hydroxy-5,6-dihydro-6-thymidyl>-L-phenylalaninate 
• 107908-77-0 ethyl N-<(5R,6R)-cis-(-)-5-hydroxy-5,6-dihydro-6-thymidyl>-L-phenylalaninate 
• 65-71-4 thymin 
• 13091-56-0 1-(2-Deoxy-β-D-erythro-pentopyranosyl)thymine 
• 50-89-5 thymidine 

Relevant articles and documents

Conformational and electronic properties of the two cis (5S,6R) and (5R,6S) diastereoisomers of 5,6-dihydroxy-5,6-dihydrothymidine: X-ray and theoretical studies

The structure of (+)-cis-(5S,6R)-5,6-dihydroxy-5,6-dihydrothymidine was obtained using X-ray crystallography [space group P21 with a = 10.130(3) A, b = 6.434(9) A, c = 11.02(5)A, and β = 112.646(2)°]. The comparison of the two cis diastereoisomers of thymidine glycol (I, II) showed several structural and conformational differences. The solid state structures appear to be in agreement with the results of 1H NMR studies which were carried out in aqueous solution. Conformational and electronic properties of the ground state of the molecules I and II were obtained using ab initio LSD-DFT theory. Only slight differences between the crystal structure and the optimized geometry are observed for each of the two oxidized nucleosides. On the other hand, molecules I and II exhibit significant differences in their electronic properties. In particular, the dipole moment of (5S,6R)-thymidine glycol (I) is twice smaller than that of the (5R,6S) diastereoisomer (II). It is noteworthy that these differences in the electronic properties between the two compounds may be related to changes in the rotameric population around the C4'-C5' bond. The repartition of the electrostatic potential is different in the two compounds. These observations lead to a better understanding of the structural changes when the above lesions are included within a DNA molecule.

Stereo-structures of Reaction Products of Thymidine Epoxides with Amines and L-Amino Acid Ethyl Esters

Reaction of thymidine epoxide (6) derived from (5R,6R)-trans-(+)-5-bromo-6-hydroxy-5,6-dihydrothymidine (2) with amines and L-amino acid ethyl esters afforded cis adduct (10) and that of the epoxide (8) derived from (5S,6S)-trans-(-)-5-bromo-6-hydroxy-5,6

Stereostructures of reaction products of thymidine epoxides with amines and L-amino acid ethyl esters

-