9-(5-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-4-thio-α(and β)-D-arabino-pentofuranosyl)-2-fluoroadenine

Base Information

Chemical Name:9-(5-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-4-thio-α(and β)-D-arabino-pentofuranosyl)-2-fluoroadenine
CAS No.:197648-61-6
Molecular Formula:C₁₉H₁₉F₂N₅O₃S
Molecular Weight:435.454
Hs Code.:

Synonyms:9-(5-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-4-thio-α(and β)-D-arabino-pentofuranosyl)-2-fluoroadenine

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Chemical Property of 9-(5-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-4-thio-α(and β)-D-arabino-pentofuranosyl)-2-fluoroadenine

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Technology Process of 9-(5-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-4-thio-α(and β)-D-arabino-pentofuranosyl)-2-fluoroadenine

There total 5 articles about 9-(5-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-4-thio-α(and β)-D-arabino-pentofuranosyl)-2-fluoroadenine 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: 58.0%

: 197648-60-5
9-(5-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-4-thio-α(and β)-D-arabino-pentofuranosyl)-2,6-diaminopurine

: Acetic acid (2R,3S,4S)-3-benzyloxy-5-(2,6-difluoro-purin-9-yl)-4-fluoro-tetrahydro-thiophen-2-ylmethyl ester

: 197648-61-6
9-(5-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-4-thio-α(and β)-D-arabino-pentofuranosyl)-2-fluoroadenine

Guidance literature:: With tert.-butylnitrite; pyridine hydrogenfluoride; at 0 ℃; for 0.5h;
DOI:10.1016/S0968-0896(00)00065-1

Reference yield:

: 1904-98-9
2,6-diaminopurine

: 197648-61-6
9-(5-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-4-thio-α(and β)-D-arabino-pentofuranosyl)-2-fluoroadenine

Guidance literature:: Multi-step reaction with 4 steps

1: 39 percent / TMSOTf; 4A MS / acetonitrile / 1 h / 20 °C

2: NH₄F*HF / dimethylformamide / 20 °C

3: 393 mg / Et₃N / acetonitrile / 20 °C

4: 58 percent / t-butyl nitrite; HF-pyridine / 0.5 h / 0 °C

With ammonium fluoride; tert.-butylnitrite; trimethylsilyl trifluoromethanesulfonate; hydrogen fluoride; pyridine hydrogenfluoride; triethylamine; In N,N-dimethyl-formamide; acetonitrile; 1: glycosylation / 2: desilylation / 3: Acetylation / 4: Substitution;
DOI:10.1016/S0968-0896(00)00065-1

Reference yield:

: 189748-60-5
Acetic acid (3S,4S,5R)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-tetrahydro-thiophen-2-yl ester

: 197648-61-6
9-(5-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-4-thio-α(and β)-D-arabino-pentofuranosyl)-2-fluoroadenine

Guidance literature:: Multi-step reaction with 4 steps

1: 39 percent / TMSOTf; 4A MS / acetonitrile / 1 h / 20 °C

2: NH₄F*HF / dimethylformamide / 20 °C

3: 393 mg / Et₃N / acetonitrile / 20 °C

4: 58 percent / t-butyl nitrite; HF-pyridine / 0.5 h / 0 °C

With ammonium fluoride; tert.-butylnitrite; trimethylsilyl trifluoromethanesulfonate; hydrogen fluoride; pyridine hydrogenfluoride; triethylamine; In N,N-dimethyl-formamide; acetonitrile; 1: glycosylation / 2: desilylation / 3: Acetylation / 4: Substitution;
DOI:10.1016/S0968-0896(00)00065-1