L-Acosamine nucleoside

Base Information

• Chemical Name: L-Acosamine nucleoside
• CAS No.: 136035-09-1
• Molecular Formula: C21H21N3O7
• Molecular Weight: 427.4073
• DSSTox Substance ID: DTXSID50929237
• Wikidata: Q82904069
• Mol file: 136035-09-1.mol

Synonyms:L-Acosamine nucleoside;136035-09-1;1-(5-O-Acetyl-3-phthalimido-2,3,6-trideoxy-alpha-L-ribo-hexofuranosyl)thymine;2,4(1H,3H)-Pyrimidinedione, 1-(5-O-acetyl-2,3,6-trideoxy-3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-alpha-L-ribo-hexofuranosyl)-5-methyl-;(S)-1-((2R,3R,5R)-3-(1,3-dioxoisoindolin-2-yl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)ethyl acetate;DTXSID50929237;AKOS040746057;[(1S)-1-[(2R,3R,5R)-3-(1,3-dioxoisoindol-2-yl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]ethyl] acetate;1-(5-O-Acetyl-3-phthalimido-2,3,6-trideoxy-.alpha.-L-ribo-hexofuranosyl)thymine;[(1S)-1-[(2R,3R,5R)-3-(1,3-dioxoisoindolin-2-yl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]ethyl] acetate;1-[5-O-Acetyl-2,3,6-trideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)hexofuranosyl]-4-hydroxy-5-methylpyrimidin-2(1H)-one;2,4(1H,3H)-Pyrimidinedione, 1-[5-O-acetyl-2,3,6-trideoxy-3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-.alpha.-L-ribo-hexofuranosyl]-5-methyl-

Chemical Property of L-Acosamine nucleoside

Chemical Property:

• Density: 1.426g/cm³
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 427.13795002
• Heavy Atom Count: 31
• Complexity: 845

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)C(C)OC(=O)C)N3C(=O)C4=CC=CC=C4C3=O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@H]([C@@H](O2)[C@H](C)OC(=O)C)N3C(=O)C4=CC=CC=C4C3=O

Technology Process of L-Acosamine nucleoside

There total 2 articles about L-Acosamine nucleoside 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:

1,5-di-O-acetyl-2,3,6-trideoxy-3-phthalimido-β-L-ribo-hexofuranose (136035-07-9) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → 1-(5-O-acetyl-3-phthalimido-2,3,6-trideoxy-α-L-ribo-hexofuranosyl)thymine (136035-09-1) + 1-(5-O-acetyl-3-phthalimido-2,3,6-trideoxy-β-L-ribo-hexofuranosyl)thymine (136035-10-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -15 ℃; for 0.5h;

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-(5-O-acetyl-3-phthalimido-2,3,6-trideoxy-α-L-ribo-hexofuranosyl)thymine (136035-09-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 200 mg / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0.5 h / -15 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile;

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

upstream raw materials:

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

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

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