3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-5'-carboxy-5',3'-dideoxyuridine

Base Information

Chemical Name:3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-5'-carboxy-5',3'-dideoxyuridine
CAS No.:661485-48-9
Molecular Formula:C₂₅H₃₅N₃O₈Si
Molecular Weight:533.654
Hs Code.:

Synonyms:3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-5'-carboxy-5',3'-dideoxyuridine

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Chemical Property of 3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-5'-carboxy-5',3'-dideoxyuridine

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Technology Process of 3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-5'-carboxy-5',3'-dideoxyuridine

There total 7 articles about 3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-5'-carboxy-5',3'-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: 67.0%

: 661485-47-8
3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-5',3'-dideoxy-5'-nitromethyluridine

: 661485-48-9
3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-5'-carboxy-5',3'-dideoxyuridine

Guidance literature:: With acetic acid; sodium nitrite; In dimethyl sulfoxide; at 40 ℃; for 28h;
DOI:10.1021/jo060457c

Reference yield:

: 661485-44-5
3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-3'-deoxyuridine

: 661485-48-9
3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-5'-carboxy-5',3'-dideoxyuridine

Guidance literature:: Multi-step reaction with 4 steps

1.1: DMSO; trifluoroacetic acid; pyridine / 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide / toluene / 1 h / 20 °C

1.2: sodium methoxide / methanol / 1.5 h / 20 °C

2.1: p-toluenesulfonic acid monohydrate / 1.5 h / 20 °C

3.1: 725 mg / NaBH₄ / ethanol / 0.67 h / 20 °C

4.1: 67 percent / NaNO₂; acetic acid / dimethylsulfoxide / 28 h / 40 °C

With pyridine; sodium tetrahydroborate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; trifluoroacetic acid; sodium nitrite; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In ethanol; dimethyl sulfoxide; toluene;
DOI:10.1021/jo060457c

Reference yield:

: 906795-53-7
3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-3'-deoxy-5'-O-(4-methoxytrityl)uridine

: 661485-48-9
3'-[N-(benzyloxycarbonyl)aminomethyl]-2'-O-tert-butyldimethylsilyl-5'-carboxy-5',3'-dideoxyuridine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 77 percent / dichloroacetic acid; triethylsilane / CH₂Cl₂ / 0.25 h / 20 °C

2.1: DMSO; trifluoroacetic acid; pyridine / 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide / toluene / 1 h / 20 °C

2.2: sodium methoxide / methanol / 1.5 h / 20 °C

3.1: p-toluenesulfonic acid monohydrate / 1.5 h / 20 °C

4.1: 725 mg / NaBH₄ / ethanol / 0.67 h / 20 °C

5.1: 67 percent / NaNO₂; acetic acid / dimethylsulfoxide / 28 h / 40 °C

With pyridine; triethylsilane; dichloro-acetic acid; sodium tetrahydroborate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; trifluoroacetic acid; sodium nitrite; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In ethanol; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1021/jo060457c