5-(Carboxymethylaminomethyl)-2-thiouridine

Base Information

• Chemical Name: 5-(Carboxymethylaminomethyl)-2-thiouridine
• CAS No.: 78173-95-2
• Molecular Formula: C₁₂H₁₇N₃O₇S
• Molecular Weight: 347.349
• DSSTox Substance ID: DTXSID60228824
• Nikkaji Number: J2.035.649I
• Wikidata: Q27133223
• Metabolomics Workbench ID: 63331
• Mol file: 78173-95-2.mol

Synonyms:5-(carboxymethylaminomethyl)-2-thiouridine;5-CMTU

Chemical Property of 5-(Carboxymethylaminomethyl)-2-thiouridine

Chemical Property:

• PSA: 189.39000
• Density: 1.72g/cm³
• LogP: -1.50520
• XLogP3: -4.5
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 347.07872106
• Heavy Atom Count: 23
• Complexity: 541

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=S)N1C2C(C(C(O2)CO)O)O)CNCC(=O)O
• Isomeric SMILES: C1=C(C(=O)NC(=S)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)CNCC(=O)O
• Uses: 5-Carboxymethylaminomethyl-2-thiouridine or mcm5S2U, is a naturally occurring 2-thio-modification of tRNA catalyzed by the action of Nfs1 enzyme on cy-tRNALyS2UUU and cy-tRNAGlU3UUC

Technology Process of 5-(Carboxymethylaminomethyl)-2-thiouridine

There total 15 articles about 5-(Carboxymethylaminomethyl)-2-thiouridine 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: 75.0%

5-pivaloyloxymethyl-2-thiouridine + Gly-tetra-n-butyl-ammonium salt (113790-35-5) → 2-thio-5-<<(carboxymethyl)amino>methyl>uridine (78173-95-2)

Guidance literature:

In ethanol; at 60 ℃; for 20h;

DOI:10.1016/j.tetlet.2015.10.023

Reference yield: 72.0%

C17H25N3O8S → 2-thio-5-<<(carboxymethyl)amino>methyl>uridine (78173-95-2)

Guidance literature:

With methylamine; In water; at 60 ℃; for 1h;

DOI:10.1016/j.tetlet.2015.10.023

Reference yield: 60.0%

{[1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl]-amino}-acetic acid tert-butyl ester (89129-09-9) → 2-thio-5-<<(carboxymethyl)amino>methyl>uridine (78173-95-2)

Guidance literature:

With water; trifluoroacetic acid; Ambient temperature;

DOI:10.1039/c39840000062

upstream raw materials:

{[1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl]-amino}-acetic acid tert-butyl ester

5-<(N-trifluoroacetyl)methoxycarbonylmethylaminomethyl>-2-thiouridine

2',3'-O-isopropylidene-2-thiouridine

2',3'-O-isopropylidene-5-pyrrolidinomethyl-2-thiouridine

Downstream raw materials:

5-carboxymethylaminomethyluridine

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