1-[3,5-O-(di-O-t-butylsilylene)-2-cyano-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

Base Information

Chemical Name:1-[3,5-O-(di-O-t-butylsilylene)-2-cyano-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine
CAS No.:753007-92-0
Molecular Formula:C₂₅H₃₃N₃O₄SSeSi
Molecular Weight:578.666
Hs Code.:

Synonyms:1-[3,5-O-(di-O-t-butylsilylene)-2-cyano-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

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Chemical Property of 1-[3,5-O-(di-O-t-butylsilylene)-2-cyano-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

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Technology Process of 1-[3,5-O-(di-O-t-butylsilylene)-2-cyano-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

There total 14 articles about 1-[3,5-O-(di-O-t-butylsilylene)-2-cyano-2-deoxy-2-phenylseleno-4-thio-β-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: 92.0%

: 753007-91-9
1-[2-deoxy-2-hydroxyimino-2-phenylseleno-3,5-O-(di-O-t-butylsilylene)-4-thio-β-D-ribofuranosyl]thymine

: 753007-92-0
1-[3,5-O-(di-O-t-butylsilylene)-2-cyano-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

Guidance literature:: With pyridine; methanesulfonyl chloride; at 0 ℃;
DOI:10.1021/ol040035u

Reference yield:

: 85272-31-7
di-tert-butylsilyl bis(trifluoromethanesulfonate)

: 753007-92-0
1-[3,5-O-(di-O-t-butylsilylene)-2-cyano-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

Guidance literature:: Multi-step reaction with 4 steps

1: 240.8 mg / imidazole / dimethylformamide / 3 h / 0 °C

2: 76 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

3: 58 percent / NH₂OH*HCl; pyridine / 9 h / 0 °C

4: 92 percent / MeSO₂Cl₂; pyridine / 0 °C

With pyridine; 1H-imidazole; hydroxylamine hydrochloride; Dess-Martin periodane; methanesulfonyl chloride; In dichloromethane; N,N-dimethyl-formamide; 2: Dess-Martin oxidation;
DOI:10.1021/ol040035u

Reference yield:

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

: 753007-92-0
1-[3,5-O-(di-O-t-butylsilylene)-2-cyano-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / acetonitrile; CH₂Cl₂ / 0 °C

2: 93 percent / Bu₄NF / tetrahydrofuran / 4 h / 0 °C

3: NaOMe / methanol / 3 h / 0 °C

4: 240.8 mg / imidazole / dimethylformamide / 3 h / 0 °C

5: 76 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

6: 58 percent / NH₂OH*HCl; pyridine / 9 h / 0 °C

7: 92 percent / MeSO₂Cl₂; pyridine / 0 °C

With pyridine; 1H-imidazole; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; sodium methylate; Dess-Martin periodane; methanesulfonyl chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 6: Dess-Martin oxidation;
DOI:10.1021/ol040035u