1-(3-Amino-2,3,6-trideoxy-beta-L-ribo-hexofuranosyl)thymine

Base Information

• Chemical Name: 1-(3-Amino-2,3,6-trideoxy-beta-L-ribo-hexofuranosyl)thymine
• CAS No.: 136035-13-7
• Molecular Formula: C11H17N3O4
• Molecular Weight: 255.2704
• DSSTox Substance ID: DTXSID10929238
• Wikidata: Q82904070
• Mol file: 136035-13-7.mol

Synonyms:Amino nucleoside;136035-13-7;1-(3-Amino-2,3,6-trideoxy-beta-L-ribo-hexofuranosyl)thymine;2,4(1H,3H)-Pyrimidinedione, 1-(3-amino-2,3,6-trideoxy-beta-L-ribo-hexofuranosyl)-5-methyl-;DTXSID10929238;1-(3-Amino-2,3,6-trideoxy-.beta.-L-ribo-hexofuranosyl)thymine;1-(3-Amino-2,3,6-trideoxyhexofuranosyl)-4-hydroxy-5-methylpyrimidin-2(1H)-one;1-[(2S,4R,5R)-4-amino-5-[(1S)-1-hydroxyethyl]tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione;2,4(1H,3H)-Pyrimidinedione, 1-(3-amino-2,3,6-trideoxy-.beta.-L-ribo-hexofuranosyl)-5-methyl-

Chemical Property of 1-(3-Amino-2,3,6-trideoxy-beta-L-ribo-hexofuranosyl)thymine

Chemical Property:

• PSA: 110.60000
• Density: 1.33g/cm³
• LogP: -0.04680
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 255.12190603
• Heavy Atom Count: 18
• Complexity: 409

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)C(C)O)N
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@@H]2C[C@H]([C@@H](O2)[C@H](C)O)N

Technology Process of 1-(3-Amino-2,3,6-trideoxy-beta-L-ribo-hexofuranosyl)thymine

There total 4 articles about 1-(3-Amino-2,3,6-trideoxy-beta-L-ribo-hexofuranosyl)thymine 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: 85.0%

1-(5-O-acetyl-3-phthalimido-2,3,6-trideoxy-β-L-ribo-hexofuranosyl)thymine (136035-10-4) → 1-(3-amino-2,3,6-trideoxy-β-L-ribo-hexofuranosyl)thymine (136035-13-7)

Guidance literature:

With methylamine; In ethanol; at 20 ℃;

DOI:10.3891/acta.chem.scand.45-0616

Reference yield:

5-O-acetyl-2,3,6-trideoxy-3-phthalimido-β-L-ribo-hexofuranose (136035-06-8) → 1-(3-amino-2,3,6-trideoxy-β-L-ribo-hexofuranosyl)thymine (136035-13-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / pyridine / CH₂Cl₂ / 3 h / 20 °C

2: 176 mg / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0.5 h / -15 °C

3: 85 percent / methylamine / ethanol / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; methylamine; In ethanol; dichloromethane; acetonitrile;

DOI:10.3891/acta.chem.scand.45-0616

Reference yield:

1,5-di-O-acetyl-2,3,6-trideoxy-3-phthalimido-β-L-ribo-hexofuranose (136035-07-9) → 1-(3-amino-2,3,6-trideoxy-β-L-ribo-hexofuranosyl)thymine (136035-13-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 176 mg / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0.5 h / -15 °C

2: 85 percent / methylamine / ethanol / 20 °C

With trimethylsilyl trifluoromethanesulfonate; methylamine; In ethanol; acetonitrile;

DOI:10.3891/acta.chem.scand.45-0616

upstream raw materials:

1-(5-O-acetyl-3-phthalimido-2,3,6-trideoxy-β-L-ribo-hexofuranosyl)thymine

5-O-acetyl-2,3,6-trideoxy-3-phthalimido-β-L-ribo-hexofuranose

1,5-di-O-acetyl-2,3,6-trideoxy-3-phthalimido-β-L-ribo-hexofuranose

2,4-bis(trimethylsiloxy)-5-methylpyrimidine