1(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-L-arabinofuranosyl) thymine

Base Information

• Chemical Name: 1(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-L-arabinofuranosyl) thymine
• CAS No.: 171721-03-2
• Molecular Formula: C₂₄H₂₁FN₂O₇
• Molecular Weight: 468.438
• DSSTox Substance ID: DTXSID201118688
• Nikkaji Number: J1.069.638K
• Mol file: 171721-03-2.mol

Synonyms:SCHEMBL4734615;CEPDPXNYCRCFRV-JTJHWIPRSA-N;DTXSID201118688;1(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-L-arabinofuranosyl) thymine;1-(2-Fluoro-3-O,5-O-dibenzoyl-2-deoxy-beta-L-arabinofuranosyl)thymine;1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-L-arabinofuranosyl) thymine;1-(3,5-Di-O-benzoyl-2-deoxy-2-fluoro-beta-L-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione;171721-03-2

Chemical Property of 1(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-L-arabinofuranosyl) thymine

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 468.13327918
• Heavy Atom Count: 34
• Complexity: 835

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2C(C(C(O2)COC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)F
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@@H]2[C@@H]([C@H]([C@@H](O2)COC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)F

Technology Process of 1(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-L-arabinofuranosyl) thymine

There total 33 articles about 1(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-L-arabinofuranosyl) 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: 61.1%

thymin (65-71-4,28806-14-6,691841-57-3) + 1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose (171866-29-8) → 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-L-arabinofuranosyl)thymine (171721-03-2)

Guidance literature:

thymin; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile; for 12h; Reflux; Green chemistry;

1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose; In acetonitrile; for 5h; Reflux; Green chemistry;

Reference yield: 42.0%

1-O-methyl-2-deoxy-2-fluoro-3,5-di-O-benzoyl-L-arabinofuranoside + thymin (65-71-4,28806-14-6,691841-57-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → silylated thymine + 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-L-arabinofuranosyl)thymine (171721-03-2)

Guidance literature:

With ammonium sulfate; hydrogen bromide; In dichloromethane; chloroform; acetic acid; benzene;

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose (3080-30-6,6974-32-9,14215-97-5,16162-35-9,20822-87-1,21138-42-1,22249-15-6,22249-17-8,26287-72-9,53403-35-3,53403-36-4,57236-69-8,70832-64-3,99395-04-7,100101-51-7,109668-83-9,120019-54-7) → 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)thymine (171721-03-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) HCl(g), AcCl, 2.) H₂O / 1.) CH₂Cl₂, 0 deg C, 2.) CH₃CN

2: 1.) SO₂Cl₂ / 1.) CH₂Cl₂, DMF, from -40 deg C to RT, 3.5 h, 2.) CH₂Cl₂, DMF, RT, 15 h

3: 65 percent / KHF₂, 48percent aq. HF / various solvent(s) / 1 h / 160 °C

4: 100 percent / HBr, AcOH / CH₂Cl₂ / 20 h / Ambient temperature

5: 1.) HMDS, (NH₄)2SO₄ / reflux, 17 h, 2.) dichloroethane, reflux, 20 h

With hydrogenchloride; ammonium sulfate; sulfuryl dichloride; potassium hydrogen bifluoride; hydrogen fluoride; water; hydrogen bromide; acetic acid; acetyl chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;

DOI:10.1021/jm960098l

upstream raw materials:

thymin

1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose

1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose

benzoyl chloride

Downstream raw materials:

clevudine

Refernces

• 1、 -. "Green synthetic process of clevudine". Paragraph 0026; 0027; 0028. . Retrieved 2019/03/29.
• 2、 -. "Process for the preparation of 2'-halo-beta-L-arabinofuranosyl nucleosides". . . Retrieved 2008/06/13.