2'-O-acetyl-3'-azidomethyl-5'-[(tert-butyldiphenylsilyloxy)methyl]-3',5'-dideoxyuridine

Base Information

Chemical Name:2'-O-acetyl-3'-azidomethyl-5'-[(tert-butyldiphenylsilyloxy)methyl]-3',5'-dideoxyuridine
CAS No.:622381-36-6
Molecular Formula:C₂₉H₃₅N₅O₆Si
Molecular Weight:577.712
Hs Code.:

Synonyms:2'-O-acetyl-3'-azidomethyl-5'-[(tert-butyldiphenylsilyloxy)methyl]-3',5'-dideoxyuridine

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Chemical Property of 2'-O-acetyl-3'-azidomethyl-5'-[(tert-butyldiphenylsilyloxy)methyl]-3',5'-dideoxyuridine

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Technology Process of 2'-O-acetyl-3'-azidomethyl-5'-[(tert-butyldiphenylsilyloxy)methyl]-3',5'-dideoxyuridine

There total 7 articles about 2'-O-acetyl-3'-azidomethyl-5'-[(tert-butyldiphenylsilyloxy)methyl]-3',5'-dideoxyuridine 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: 86.0%

: 10457-14-4
O,O'-bis-(trimethylsilyl)uracil

: 674790-06-8
1,2-di-O-acetyl-3-azidomethyl-5-[(tert-butyldiphenylsiloxy)methyl]-3,5-dideoxyribofuranose

: 622381-36-6
2'-O-acetyl-3'-azidomethyl-5'-[(tert-butyldiphenylsilyloxy)methyl]-3',5'-dideoxyuridine

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/ol035619v

Reference yield:

: 134056-14-7
3,5-dideoxy-3-<(benzoyloxy)methyl>-1,2-O-isopropylidene-α-D-allofuranose

: 622381-36-6
2'-O-acetyl-3'-azidomethyl-5'-[(tert-butyldiphenylsilyloxy)methyl]-3',5'-dideoxyuridine

Guidance literature:: Multi-step reaction with 6 steps

1: 13.87 g / aq. NaOH / propan-2-ol / 0.5 h / 70 °C

2: Et₃N / CH₂Cl₂ / 20 °C

3: 6.26 g / NaN₃ / dimethylformamide / 3 h / 60 °C

4: 70 percent / BCl₃ / CH₂Cl₂; hexane / 0.33 h / -78 °C

5: 87 percent / pyridine / 24 h / 20 °C

6: 86 percent / TMSOTf / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; sodium hydroxide; sodium azide; trimethylsilyl trifluoromethanesulfonate; boron trichloride; triethylamine; In hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/ol035619v

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 622381-36-6
2'-O-acetyl-3'-azidomethyl-5'-[(tert-butyldiphenylsilyloxy)methyl]-3',5'-dideoxyuridine

Guidance literature:: Multi-step reaction with 6 steps

1: 13.87 g / aq. NaOH / propan-2-ol / 0.5 h / 70 °C

2: Et₃N / CH₂Cl₂ / 20 °C

3: 6.26 g / NaN₃ / dimethylformamide / 3 h / 60 °C

4: 70 percent / BCl₃ / CH₂Cl₂; hexane / 0.33 h / -78 °C

5: 87 percent / pyridine / 24 h / 20 °C

6: 86 percent / TMSOTf / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; sodium hydroxide; sodium azide; trimethylsilyl trifluoromethanesulfonate; boron trichloride; triethylamine; In hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/ol035619v