1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-D-ribofuranosyl>thymine

Base Information

• Chemical Name: 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-D-ribofuranosyl>thymine
• CAS No.: 137719-37-0
• Molecular Formula: C₂₆H₃₂N₂O₃SSi
• Molecular Weight: 480.703
• Mol file: 137719-37-0.mol

Synonyms:1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-D-ribofuranosyl>thymine

Chemical Property of 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-D-ribofuranosyl>thymine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-D-ribofuranosyl>thymine

There total 7 articles about 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-D-ribofuranosyl>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:

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thioribofuranose (137719-23-4) + thymin (65-71-4,28806-14-6,691841-57-3) → 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-D-ribofuranosyl>thymine (137719-37-0) + 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-β-D-ribofuranosyl>thymine (137819-78-4)

Guidance literature:

With chloro-trimethyl-silane; potassium nonaflate; 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile; at 25 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jm00081a015

Reference yield:

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one (102717-29-3) → 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-D-ribofuranosyl>thymine (137719-37-0)

Guidance literature:

Multi-step reaction with 7 steps

1: aq. NaOH / ethanol / 1 h

2: dimethylsulfoxide; toluene / 2 h / 25 °C

3: 85 percent / PPh₃, imidazole, iodine / toluene / 1 h / Heating

4: 1.) tetrabutylammonium hydroxide / 1.) MeOH, toluene, 2.) toluene, 18 h

5: DIBAL-H / hexane / 0.5 h / -78 °C

6: pyridine, DMAP

7: potassium nonafluorobutanesulfonate, HMDS, TMSCl / acetonitrile / 25 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; chloro-trimethyl-silane; tetra(n-butyl)ammonium hydroxide; iodine; diisobutylaluminium hydride; potassium nonaflate; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; In ethanol; hexane; dimethyl sulfoxide; toluene; acetonitrile;

DOI:10.1021/jm00081a015

Reference yield:

5-0-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thioribofuranose → 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-D-ribofuranosyl>thymine (137719-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine, DMAP

2: potassium nonafluorobutanesulfonate, HMDS, TMSCl / acetonitrile / 25 °C

With pyridine; dmap; chloro-trimethyl-silane; potassium nonaflate; 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile;

DOI:10.1021/jm00081a015

upstream raw materials:

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thioribofuranose

thymin

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

5-<(tert-butyldiphenylsilyl)oxy>-4(S)-hydroxypentanoic acid methyl ester

Downstream raw materials:

1-(2,3-dideoxy-4-thio-α-D-ribofuranosyl)thymine

1-(2,3-dideoxy-4-thio-β-D-ribofuranosyl)thymine