9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-ribofuranosyl>-2,6-dichloropurine

Base Information

Chemical Name:9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-ribofuranosyl>-2,6-dichloropurine
CAS No.:137719-25-6
Molecular Formula:C₂₆H₂₈Cl₂N₄OSSi
Molecular Weight:543.592
Hs Code.:

Synonyms:9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-ribofuranosyl>-2,6-dichloropurine

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Chemical Property of 9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-ribofuranosyl>-2,6-dichloropurine

Chemical Property:

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Technology Process of 9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-ribofuranosyl>-2,6-dichloropurine

There total 7 articles about 9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-ribofuranosyl>-2,6-dichloropurine 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:

: 137719-23-4
1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thioribofuranose

: 5451-40-1
2,6 dichloropurine

: 137719-25-6
9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-ribofuranosyl>-2,6-dichloropurine

: 137819-72-8
9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-β-ribofuranosyl>-2,6-dichloropurine

Guidance literature:: With diethylaluminium chloride; In toluene; acetonitrile; at 0 - 25 ℃; for 0.25h; Yield given. Title compound not separated from byproducts;
DOI:10.1021/jm00081a015

Reference yield:

: 102717-29-3
(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

: 137719-25-6
9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-ribofuranosyl>-2,6-dichloropurine

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: Et₂AlCl / acetonitrile; toluene / 0.25 h / 0 - 25 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; tetra(n-butyl)ammonium hydroxide; iodine; diethylaluminium chloride; diisobutylaluminium hydride; triphenylphosphine; In ethanol; hexane; dimethyl sulfoxide; toluene; acetonitrile;
DOI:10.1021/jm00081a015

Reference yield:

: 5-0-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thioribofuranose

: 137719-25-6
9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-α-ribofuranosyl>-2,6-dichloropurine

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine, DMAP

2: Et₂AlCl / acetonitrile; toluene / 0.25 h / 0 - 25 °C

With pyridine; dmap; diethylaluminium chloride; In toluene; acetonitrile;
DOI:10.1021/jm00081a015