1-<5-O-benzyl-3-deoxy-3-C-(fluoromethyl)-2-O-(methylsulfonyl)-β-D-erythro-pentofuranosyl>thymine

Base Information

Chemical Name:1-<5-O-benzyl-3-deoxy-3-C-(fluoromethyl)-2-O-(methylsulfonyl)-β-D-erythro-pentofuranosyl>thymine
CAS No.:146035-71-4
Molecular Formula:C₁₉H₂₃FN₂O₇S
Molecular Weight:442.465
Hs Code.:

Synonyms:1-<5-O-benzyl-3-deoxy-3-C-(fluoromethyl)-2-O-(methylsulfonyl)-β-D-erythro-pentofuranosyl>thymine

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Chemical Property of 1-<5-O-benzyl-3-deoxy-3-C-(fluoromethyl)-2-O-(methylsulfonyl)-β-D-erythro-pentofuranosyl>thymine

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Technology Process of 1-<5-O-benzyl-3-deoxy-3-C-(fluoromethyl)-2-O-(methylsulfonyl)-β-D-erythro-pentofuranosyl>thymine

There total 10 articles about 1-<5-O-benzyl-3-deoxy-3-C-(fluoromethyl)-2-O-(methylsulfonyl)-β-D-erythro-pentofuranosyl>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: 84.0%

: 124-63-0
methanesulfonyl chloride

: 133713-87-8
1-<5-O-benzyl-3-C-(fluoromethyl)-3-deoxy-β-D-erythro-pentofuranosyl>thymine

: 146035-71-4
1-<5-O-benzyl-3-deoxy-3-C-(fluoromethyl)-2-O-(methylsulfonyl)-β-D-erythro-pentofuranosyl>thymine

Guidance literature:: With pyridine; at 0 ℃; for 5h;
DOI:10.1021/jm00055a006

Reference yield:

: 69832-48-0
((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol

: 146035-71-4
1-<5-O-benzyl-3-deoxy-3-C-(fluoromethyl)-2-O-(methylsulfonyl)-β-D-erythro-pentofuranosyl>thymine

Guidance literature:: Multi-step reaction with 10 steps

1: 40 percent / (dimethylamino)sulfur trifluoride (DAST), pyridine / CH₂Cl₂ / 4 h / Ambient temperature

2: 2N aq. H₂SO₄ / methanol / 8 h / Ambient temperature

3: NaHCO₃, aq. sodium metaperiodate / ethanol / 4 h / Ambient temperature

4: NaBH₄ / 18 h / Ambient temperature

5: 1.) NaH / 1.) DMF, 0-5 deg C, 30 min, 2.) DMF, RT, overnight

6: 80percent aq. trifluoroacetic acid / 2 h / 0 °C

7: pyridine / 2 h / Ambient temperature

8: 84 percent / HMDS, TCS, C₄F₉SO₃K / acetonitrile / 24 h / Heating

9: 85 percent / NH₃ / methanol / 24 h / Ambient temperature

10: 84 percent / pyridine / 5 h / 0 °C

With pyridine; sodium tetrahydroborate; sodium periodate; dimethylaminosulphur trifluoride; C₄F₉SO₃K; sulfuric acid; ammonia; sodium hydride; sodium hydrogencarbonate; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In methanol; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/jm00055a006

Reference yield:

: 146035-65-6
3-deoxy-3-(fluoromethyl)-1,2-O-isopropylidene-α-D-ribofuranose

: 146035-71-4
1-<5-O-benzyl-3-deoxy-3-C-(fluoromethyl)-2-O-(methylsulfonyl)-β-D-erythro-pentofuranosyl>thymine

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DMF, 0-5 deg C, 30 min, 2.) DMF, RT, overnight

2: 80percent aq. trifluoroacetic acid / 2 h / 0 °C

3: pyridine / 2 h / Ambient temperature

4: 84 percent / HMDS, TCS, C₄F₉SO₃K / acetonitrile / 24 h / Heating

5: 85 percent / NH₃ / methanol / 24 h / Ambient temperature

6: 84 percent / pyridine / 5 h / 0 °C

With pyridine; C₄F₉SO₃K; ammonia; sodium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In methanol; acetonitrile;
DOI:10.1021/jm00055a006