1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-chlorocytosine

Base Information

Chemical Name:1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-chlorocytosine
CAS No.:178687-97-3
Molecular Formula:C₂₃H₁₉ClFN₃O₆
Molecular Weight:487.872
Hs Code.:

Synonyms:

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

Chemical Property:

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

There total 13 articles about 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-chlorocytosine 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:

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

: 178687-97-3
1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-chlorocytosine

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 / 2.) dichloroethane, reflux, 24 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

Reference yield:

: 98-88-4
benzoyl chloride

: 178687-97-3
1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-chlorocytosine

Guidance literature:: Multi-step reaction with 9 steps

1: 98 percent / pyridine / 3 h / Ambient temperature

2: 1percent HCl / methanol / 30 h / Ambient temperature

3: pyridine / 3 h / Ambient temperature

4: AcOH, conc. H₂SO₄ / Ambient temperature

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

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

7: 65 percent / KHF₂, 48percent aq. HF / various solvent(s) / 1 h / 160 °C

8: 100 percent / HBr, AcOH / CH₂Cl₂ / 20 h / Ambient temperature

9: 1.) HMDS, (NH₄)2SO₄ / 2.) dichloroethane, reflux, 24 h

With pyridine; hydrogenchloride; ammonium sulfate; sulfuryl dichloride; potassium hydrogen bifluoride; sulfuric acid; hydrogen fluoride; water; hydrogen bromide; acetic acid; acetyl chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; dichloromethane;
DOI:10.1021/jm960098l

Reference yield:

: 166411-40-1
5-O-benzoyl-1,2-O-isopropylidene-α-L-erythro-pentofuranose-3-ulose

: 178687-97-3
1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-chlorocytosine

Guidance literature:: Multi-step reaction with 10 steps

1: 79 percent / NaBH₄, H₂O / ethanol / 4 h / Ambient temperature

2: 98 percent / pyridine / 3 h / Ambient temperature

3: 1percent HCl / methanol / 30 h / Ambient temperature

4: pyridine / 3 h / Ambient temperature

5: AcOH, conc. H₂SO₄ / Ambient temperature

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

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

8: 65 percent / KHF₂, 48percent aq. HF / various solvent(s) / 1 h / 160 °C

9: 100 percent / HBr, AcOH / CH₂Cl₂ / 20 h / Ambient temperature

10: 1.) HMDS, (NH₄)2SO₄ / 2.) dichloroethane, reflux, 24 h

With pyridine; hydrogenchloride; ammonium sulfate; sodium tetrahydroborate; sulfuryl dichloride; potassium hydrogen bifluoride; sulfuric acid; hydrogen fluoride; water; hydrogen bromide; acetic acid; acetyl chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; ethanol; dichloromethane;
DOI:10.1021/jm960098l