2,3'-ANHYDROTHYMIDINE

Base Information

• Chemical Name: 2,3'-ANHYDROTHYMIDINE
• CAS No.: 15981-92-7
• Molecular Formula: C10H12N2O4
• Molecular Weight: 224.216
• Mol file: 15981-92-7.mol

Synonyms:2,5-Methano-5H,9H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one,2,3-dihydro-3-(hydroxymethyl)-8-methyl- (7CI);2,5-Methano-5H,9H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one,2,3-dihydro-3-(hydroxymethyl)-8-methyl-, [2R-(2a,3b,5a)]-;2,3'-Anhydro-1-(2'-deoxy-b-D-threo-pentofuranosyl)thymine;2,3'-O-Cyclothymidine;NSC 144601;O2,3'-Cyclothymidine;

Chemical Property of 2,3'-ANHYDROTHYMIDINE

Chemical Property:

• Appearance/Colour: White Powder
• Melting Point: 246-247 °C
• Boiling Point: 381.8 °C at 760 mmHg
• PKA: 13.97±0.10(Predicted)
• Flash Point: 184.7 °C
• PSA: 64.35000
• Density: 1.72 g/cm³
• LogP: -0.07130
• Storage Temp.: −20°C

Purity/Quality:

97% ^*data from raw suppliers

2,3’-Anhydrothymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: An intermediate in the preparation of thymidine derivatives

Technology Process of 2,3'-ANHYDROTHYMIDINE

There total 20 articles about 2,3'-ANHYDROTHYMIDINE 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: 93.0%

Methoxy-acetic acid (1R,10R,11R)-4-methyl-5-oxo-8,13-dioxa-2,6-diaza-tricyclo[8.2.1.02,7]trideca-3,6-dien-11-yl ester (142409-85-6) → 2,3'-anhydrothymidine (15981-92-7)

Guidance literature:

With ammonia; In methanol; for 0.25h; Ambient temperature;

DOI:10.1016/S0040-4039(00)74215-8

Reference yield: 88.0%

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 2,3'-anhydrothymidine (15981-92-7)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In acetonitrile; at 0 ℃; for 5h; other temperature, solvents;

DOI:10.1080/07328319608002136

Reference yield: 82.0%

1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)thymine (152039-45-7) → 2,3'-anhydrothymidine (15981-92-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 20h; Ambient temperature;

DOI:10.1055/s-1995-4070

upstream raw materials:

thymidine

2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine

Methoxy-acetic acid (1R,10R,11R)-4-methyl-5-oxo-8,13-dioxa-2,6-diaza-tricyclo[8.2.1.0^2,7]trideca-3,6-dien-11-yl ester

1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-methylsulfonyl-α,β-D-erythro-pentofuranosyl)thymine

Downstream raw materials:

3'-azido-2',3'-deoxythymidine

5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-(phenylseleno)thymidine

1-((2R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)- dione

[(2R,3R,5R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxymethyl]-phosphonic acid monomethyl ester