1-(2'-O-acetyl-6'-O-benzoyl-5'-deoxy-3'-O-mesyl-β-D-allofuranosyl)thymine

Base Information

Chemical Name:1-(2'-O-acetyl-6'-O-benzoyl-5'-deoxy-3'-O-mesyl-β-D-allofuranosyl)thymine
CAS No.:130481-56-0
Molecular Formula:C₂₁H₂₄N₂O₁₀S
Molecular Weight:496.495
Hs Code.:

Synonyms:1-(2'-O-acetyl-6'-O-benzoyl-5'-deoxy-3'-O-mesyl-β-D-allofuranosyl)thymine

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Chemical Property of 1-(2'-O-acetyl-6'-O-benzoyl-5'-deoxy-3'-O-mesyl-β-D-allofuranosyl)thymine

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Technology Process of 1-(2'-O-acetyl-6'-O-benzoyl-5'-deoxy-3'-O-mesyl-β-D-allofuranosyl)thymine

There total 6 articles about 1-(2'-O-acetyl-6'-O-benzoyl-5'-deoxy-3'-O-mesyl-β-D-allofuranosyl)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: 46.0%

: 130481-55-9,130481-62-8
6-O-benzoyl-5-deoxy-1,2-di-O-acetyl-3-O-mesyl-α-D-allofuranose

: 65-71-4,28806-14-6,691841-57-3
thymin

: 130481-56-0
1-(2'-O-acetyl-6'-O-benzoyl-5'-deoxy-3'-O-mesyl-β-D-allofuranosyl)thymine

Guidance literature:: With chloro-trimethyl-silane; trifluorormethanesulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile; at 80 ℃; for 5h;
DOI:10.1016/S0040-4039(00)94484-8

Reference yield:

: 130481-54-8
6-O-benzoyl-5-deoxy-1,2-O-isopropylidene-3-O-mesyl-α-D-allofuranose

: 130481-56-0
1-(2'-O-acetyl-6'-O-benzoyl-5'-deoxy-3'-O-mesyl-β-D-allofuranosyl)thymine

Guidance literature:: Multi-step reaction with 2 steps

1: AcOH, conc. H₂SO₄ / CH₂Cl₂ / 16 h / 4 °C

2: 46 percent / hexamethyldisilazane, chlorotrimethylsilane, trifluoromethanesulfonic acid / acetonitrile / 4 h / Heating

With chloro-trimethyl-silane; trifluorormethanesulfonic acid; sulfuric acid; acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; acetonitrile;
DOI:10.1021/jm00094a014

Reference yield:

: 14728-80-4
1,2:5,6-di-O-isopropylidene-3-O-(methylsulphonyl)-α-D-allofuranose

: 130481-56-0
1-(2'-O-acetyl-6'-O-benzoyl-5'-deoxy-3'-O-mesyl-β-D-allofuranosyl)thymine

Guidance literature:: Multi-step reaction with 6 steps

1: 79 percent / 80percent aq. AcOH / 25 °C

2: 68 percent / pyridine / 16 h / -30 deg C --> 25 deg C

3: 82 percent / DMAP / acetonitrile / 16 h / 25 °C

4: 92 percent / Bu₃SnH, AIBN / toluene / 5 h / 120 °C

5: 88 percent / AcOH, H₂SO₄ / CHCl₃ / 16 h / 4 °C

6: 46 percent / HMDS, TMS-Cl, CF₃SO₃H / acetonitrile / 5 h / 80 °C

With pyridine; dmap; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; sulfuric acid; tri-n-butyl-tin hydride; acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In chloroform; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)94484-8