Spongothymidine

Base Information

• Chemical Name: Spongothymidine
• CAS No.: 605-23-2
• Molecular Formula: C10H14N2O6
• Molecular Weight: 258.231
• Hs Code.: 29349990
• European Community (EC) Number: 210-083-7
• UNII: NS9U4BEG7Y
• DSSTox Substance ID: DTXSID201194189
• Nikkaji Number: J20.575C
• Wikidata: Q27149733
• Metabolomics Workbench ID: 121258
• ChEMBL ID: CHEMBL103283
• Mol file: 605-23-2.mol

Synonyms:1 beta-D-arabinofuranosylthymine;ara-T;arabinofuranosylthymine;arabinosylthymine;spongothymidine;thymine arabinoside

Chemical Property of Spongothymidine

Chemical Property:

• Refractive Index: 1.618
• PSA: 124.78000
• Density: 1.576g/cm³
• LogP: -2.54350
• Storage Temp.: 2-8°C
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 258.08518617
• Heavy Atom Count: 18
• Complexity: 409

Purity/Quality:

99%, ^*data from raw suppliers

1-(B-D-Arabinofuranosyl)thymine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O

Technology Process of Spongothymidine

There total 20 articles about Spongothymidine 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%

O-2,2'-cyclo-5-methyluridine (22423-26-3) → thymine arabinoside (605-23-2,642082-80-2)

Guidance literature:

With ammonium hydroxide; at 70 ℃; for 14h;

DOI:10.1246/cl.1994.605

Reference yield: 66.0%

5-(p-tolylthiomethyl)-1-β-D-arabinofuranosyluracil (88054-44-8) → thymine arabinoside (605-23-2,642082-80-2)

Guidance literature:

With nickel; In ethanol; Heating;

DOI:10.1039/c39830000877

Reference yield: 65.0%

2,2'-anhydro-5'-O-tert-butyldiphenylsilyl-3'-O-ethylphosphonoacetyl-5-methyluridine → 5'-O-tert-butyldiphenylsilyl-O2-2'-anhydro-5-methyluridine (171763-19-2) + 1-(5-O-tert-butyldiphenylsilyl-β-D-arabinofuranosyl)thymine + thymine arabinoside (605-23-2,642082-80-2)

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 0.333333h; Alkaline hydrolysis;

DOI:10.1016/S0040-4020(98)00653-X

upstream raw materials:

methanesulfonyl chloride

1-(5'-O-trityl-β-D-ribofuranosyl)thymine

O-2,2'-cyclo-5-methyluridine

trimethylaluminum

Downstream raw materials:

Phosphoric acid mono-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester

Sodium; {[(2R,3S,4S,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryl}-acetate

1-(Tri-O-acetyl-β-D-arabinofuranosyl)-thymin

Refernces

• 1、 Ozaki, Hiroaki,Nakajima, Kiyohiro,Tatsui, Kaoru,Izumi, Chieko,Kuwahara, Masayasu,Sawai, Hiroaki. "Convenient synthesis of oligodeoxyribonucleotides bearing arabinofuranosyl pyrimidine derivatives and its duplex formation with complementary DNA". . p. 2441 - 2443. Retrieved 2007/10/03.
• 2、 -. "Nucleoside analogue phosphates for topical use". . . Retrieved 2008/06/13.