[1',2',3',4',5'-13C5]ribothymidine

Base Information

• Chemical Name: [1',2',3',4',5'-13C5]ribothymidine
• CAS No.: 159496-17-0
• Molecular Formula: C10H14 N2 O6
• Molecular Weight: 263.27
• DSSTox Substance ID: DTXSID80473233
• Nikkaji Number: J820.682A
• Wikidata: Q82302511
• Mol file: 159496-17-0.mol

Synonyms:159496-17-0;[1',2',3',4',5'-13C5]ribothymidine;5-Methyluridine-1',2',3',4',5'-13C5;1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxy(113C)methyl)(2,3,4,5-13C4)oxolan-2-yl]-5-methylpyrimidine-2,4-dione;CTK8F2336;DTXSID80473233;J-009612

Chemical Property of [1',2',3',4',5'-13C5]ribothymidine

Chemical Property:

• PSA: 124.78000
• LogP: -2.54350
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 263.10196035
• Heavy Atom Count: 18
• Complexity: 409

Purity/Quality:

97% ^*data from raw suppliers

5-METHYL-[1',2',3',4',5'-13C5]URIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[13C@H]2[13C@@H]([13C@@H]([13C@H](O2)[13CH2]O)O)O
• Uses: Labeled 5-Methyluridine, a primary degradation product of tRNA, Labeled 5-Methyluridine, a primary degradation product of tRNA, an urinary nucleoside as biological marker for patients with colorectal cancer.

Technology Process of [1',2',3',4',5'-13C5]ribothymidine

There total 15 articles about [1',2',3',4',5'-13C5]ribothymidine 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: 84.0%

[ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)-5-methyluracil (503173-76-0) → D-[ribose-13C5]-5-methyluridine (159496-17-0,478510-98-4,478511-00-1)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 48h;

DOI:10.1016/S0040-4020(02)01246-2

Reference yield:

<1,2,3,4,5-13C5>-1,2-O-isopropylidene-α-D-ribofuranose (238096-51-0) → D-[ribose-13C5]-5-methyluridine (159496-17-0,478510-98-4,478511-00-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 95 percent / pyridine / 3 h / 20 °C

2.1: 87 percent / H₂SO₄; AcOH / 20 °C

3.1: HMDS; (NH₄)2SO₄ / Heating

3.2: 89 percent / TMSOTf / CH₂Cl₂ / 3.5 h / Heating

4.1: 84 percent / NH₃ / methanol / 48 h / 20 °C

With pyridine; ammonium sulfate; sulfuric acid; ammonia; acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol;

DOI:10.1016/S0040-4020(02)01246-2

Reference yield:

[ribose-13C5]-3,5-di-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose (503173-74-8) → D-[ribose-13C5]-5-methyluridine (159496-17-0,478510-98-4,478511-00-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 87 percent / H₂SO₄; AcOH / 20 °C

2.1: HMDS; (NH₄)2SO₄ / Heating

2.2: 89 percent / TMSOTf / CH₂Cl₂ / 3.5 h / Heating

3.1: 84 percent / NH₃ / methanol / 48 h / 20 °C

With ammonium sulfate; sulfuric acid; ammonia; acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol;

DOI:10.1016/S0040-4020(02)01246-2

upstream raw materials:

thymin

[13C5]-1,2-di-O-acetyl-3,5-di-O-benzoyl-α,β-D-ribofuranose

[ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)-5-methyluracil

<1,2,3,4,5-13C5>-1,2-O-isopropylidene-α-D-ribofuranose

Downstream raw materials:

D-thymidine-1'2'3'4'5'-13C₅

C₂₆⁽¹³⁾C₅H₃₂N₂O₇