2',3'-Dideoxythymidine

Base Information

• Chemical Name: 2',3'-Dideoxythymidine
• CAS No.: 3416-05-5
• Molecular Formula: C10H14N2O4
• Molecular Weight: 226.232
• Hs Code.: 29349990
• Mol file: 3416-05-5.mol

Synonyms:1-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione;3'-Deoxythymidine;D 2T;2,4(1H,3H)-pyrimidinedione, 5-methyl-1-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furanyl]-;1-(5-Hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione;

Chemical Property of 2',3'-Dideoxythymidine

Chemical Property:

• Melting Point: 155-156 oC
• PKA: 9.55±0.10(Predicted)
• PSA: 84.32000
• Density: 1.332g/cm³
• LogP: -0.48510
• Storage Temp.: 2-8°C

Purity/Quality:

98%, ^*data from raw suppliers

3'-Deoxythymidine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: 3’-Deoxythymidine inhibits the ability of bacteriophage T7 to infect Escherichia coli by inhibiting phage DNA synthesis. Also, it is a precursor of DNA polymerase β inhibitor. Research tool for antiviral and anticancer studies.

Technology Process of 2',3'-Dideoxythymidine

There total 85 articles about 2',3'-Dideoxythymidine 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: 100.0%

1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine (131118-68-8) → 3'-Deoxythymidine (3416-05-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/j.chembiol.2019.04.010

Reference yield: 93.0%

3'-deoxy-5'-O-triphenylmethylthymidine (107036-54-4) → 3'-Deoxythymidine (3416-05-5)

Guidance literature:

With acetic acid; at 100 ℃; for 0.166667h;

DOI:10.1021/jo00290a024

Reference yield: 92.8%

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 3'-Deoxythymidine (3416-05-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In 1,4-dioxane; under 760 Torr;

DOI:10.1021/jm00055a009

upstream raw materials:

1-((2R)-5c-hydroxymethyl-4c-iodo-tetrahydro-[2r]furyl)-5-methyl-1H-pyrimidine-2,4-dione

3'-deoxy-5'-O-(phenoxythiocarbonyl)thymidine

1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>thymine

3'-deoxy-5'-O-triphenylmethylthymidine

Downstream raw materials:

Phosphoric acid (2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

6-(hexyloxy)-9-<(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl>-9H-purine

2',3'-dideoxy-5-hydroxymethyluridine

[14C]-Deoxythymidine monophosphate

Refernces

• 1、 Filichev, Vyacheslav V.,Vester, Birte,Pedersen, Erik B.. "Hexofuranosyl thymidines inserted into oligodeoxynucleotides via their two exocyclic hydroxy groups. Oligo synthesis and RNase H activity". . p. 2843 - 2851. Retrieved 2004.
• 2、 Banuelos-Sanchez, Guillermo,Sanchez, Laura,Benitez-Guijarro, Maria,Sanchez-Carnerero, Valentin,Salvador-Palomeque, Carmen,Tristan-Ramos, Pablo,Benkaddour-Boumzaouad, Meriem,Morell, Santiago,Garcia-Puche, Jose L.,Heras, Sara R.,Franco-Montalban, Francisco,Tamayo, Juan A.,Garcia-Perez, Jose L.. "Synthesis and Characterization of Specific Reverse Transcriptase Inhibitors for Mammalian LINE-1 Retrotransposons". . p. 1095 - 14,1109. Retrieved 2019/08/13.
• 3、 -. "Synthesis of 2', 3'-Dideoxynucleosides for Automated DNA Synthesis and Pyrophosphorolysis Activated Polymerization". . . Retrieved 2011/12/13.