2'-Deoxy-L-thymidine Chemical Properties

Melting point:

188-190°C

alpha 

D20 -20.3° (c = 0.192 in water)

Density 

1.452±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

H2O: soluble10mg/mL (clear solution)

pka

9.55±0.10(Predicted)

form 

powder

color 

white to beige

optical activity

[α]/D -15 to -22°, c = 1 in H2O

Water Solubility 

H2O: 10mg/mL (clear solution)

InChI

InChI=1/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/s3

InChIKey

IQFYYKKMVGJFEH-CSMHCCOUSA-N

SMILES

C1(=O)N([C@@H]2C[C@@H](O)[C@H](CO)O2)C=C(C)C(=O)N1 |&1:3,5,7,r|

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

24/25

WGK Germany 

3

RTECS 

UV9048500

HS Code 

29349990

2'-Deoxy-L-thymidine Usage And Synthesis

Description

Telbivudine is a b-L-thymidine nucleoside analog launched for the once-daily oral treatment of chronic hepatitis B virus (HBV) infection. It is the fourth nucleoside or nucleotide analog to be marketed for this indication. The previous drugs from this class include lamivudine, a deoxythiacytosine analog, adefovir, a nucleotide analog, and entecavir, a guanosine analog. Adefovir, entecavir, and telbivudine are specifically indicated for HBV, whereas lamivudine is indicated for both HBV and HIV infections. Telbivudine is efficiently phosphorylated by cellular kinases to the active triphosphate derivative, which inhibits HBV DNA polymerase by competing with the natural substrate, thymidine- 5’-triphosphate.

Chemical Properties

2'-Deoxy-L-thymidine is White Solid

Originator

Idenix (US)

Uses

Nucleoside analog; specific inhibitor of hepatitis B virus (HBV) replication. Antiviral.

Uses

Telbivudine(Tyzeka, Sebivo) is an antiviral drug used in the treatment of hepatitis B infection. Clinical trials have shown it to be significantly more effective than lamivudine or adefovir, and less likely to cause resistance. Telbivudine is a synthetic

Definition

ChEBI: A pyrimidine 2'-deoxyribonucleoside that is the L-enantiomer of thymine. A synthetic thymidine nucleoside analogue with activity against HBV DNA polymerase.

brand name

(Novirio).

Synthesis

Preparation of L-thymidine: L-3',5'-diacetylthymidine (7.15 g, 21.9 mmol) was dissolved in methanol (36 mL). An 8.4 wt% ammonia/methanol solution was slowly added dropwise to this solution at room temperature. The reaction mixture was stirred at 60°C for 3 days. After completion of the reaction, the solvent was removed by concentration under reduced pressure. Ethanol (21 mL) was added to the residue and stirring was continued for 1.5 hours at room temperature. The crystals formed were collected by filtration, washed twice with ethanol (3 mL) and finally dried under reduced pressure to afford 1-((2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (4.95 g, 93.4% yield).

References

[1] Patent: EP1348712, 2003, A1. Location in patent: Page/Page column 19
[2] Patent: CN106831916, 2017, A. Location in patent: Paragraph 0049; 0050
[3] Patent: US2009/18325, 2009, A1. Location in patent: Page/Page column 5-6

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