N⁶,N⁶-bis(tert-Butoxycarbonyl)-5′-amino-5′-N-(tert-butoxycarbonyl)-5′-N-[(1-benzylquinol-4-on-3-yl)sulfonyl]-5′-deoxy-2′,3′-Oisopropylideneadenosine

Base Information

• Chemical Name: N⁶,N⁶-bis(tert-Butoxycarbonyl)-5′-amino-5′-N-(tert-butoxycarbonyl)-5′-N-[(1-benzylquinol-4-on-3-yl)sulfonyl]-5′-deoxy-2′,3′-Oisopropylideneadenosine
• CAS No.: 1447236-91-0
• Molecular Formula: C₄₄H₅₃N₇O₁₂S
• Molecular Weight: 904.011
• Mol file: 1447236-91-0.mol

Synonyms:N⁶,N⁶-bis(tert-Butoxycarbonyl)-5′-amino-5′-N-(tert-butoxycarbonyl)-5′-N-[(1-benzylquinol-4-on-3-yl)sulfonyl]-5′-deoxy-2′,3′-Oisopropylideneadenosine

Chemical Property of N⁶,N⁶-bis(tert-Butoxycarbonyl)-5′-amino-5′-N-(tert-butoxycarbonyl)-5′-N-[(1-benzylquinol-4-on-3-yl)sulfonyl]-5′-deoxy-2′,3′-Oisopropylideneadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶,N⁶-bis(tert-Butoxycarbonyl)-5′-amino-5′-N-(tert-butoxycarbonyl)-5′-N-[(1-benzylquinol-4-on-3-yl)sulfonyl]-5′-deoxy-2′,3′-Oisopropylideneadenosine

There total 6 articles about N⁶,N⁶-bis(tert-Butoxycarbonyl)-5′-amino-5′-N-(tert-butoxycarbonyl)-5′-N-[(1-benzylquinol-4-on-3-yl)sulfonyl]-5′-deoxy-2′,3′-Oisopropylideneadenosine 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: 85.0%

N6,N6-bis(tert-butoxycarbonyl)-2',3'-O-isopropylideneadenosine (1152172-19-4) + tert-butyl (1-benzylquinol-4-on-3-yl)sulfonylcarbamate (1447236-89-6) → N6,N6-bis(tert-Butoxycarbonyl)-5′-amino-5′-N-(tert-butoxycarbonyl)-5′-N-[(1-benzylquinol-4-on-3-yl)sulfonyl]-5′-deoxy-2′,3′-Oisopropylideneadenosine (1447236-91-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 22 ℃; for 1.08333h; Inert atmosphere;

DOI:10.1021/jo400976f

Reference yield:

tert-butyl [2-(2-fluorophenyl)-2-oxoethyl]sulfonylcarbamate (1447236-83-0) → N6,N6-bis(tert-Butoxycarbonyl)-5′-amino-5′-N-(tert-butoxycarbonyl)-5′-N-[(1-benzylquinol-4-on-3-yl)sulfonyl]-5′-deoxy-2′,3′-Oisopropylideneadenosine (1447236-91-0)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 1.5 h / 22 °C / Inert atmosphere

2: tetrahydrofuran-d8 / 0.17 h / 22 °C / Inert atmosphere

3: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 22 °C / Inert atmosphere

4: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1.08 h / 0 - 22 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; sodium hydride; triphenylphosphine; In tetrahydrofuran; tetrahydrofuran-d8; mineral oil; 4: |Mitsunobu Displacement;

DOI:10.1021/jo400976f

Reference yield:

tert-butyl [3-(2-fluorophenyl)-1-((benzylamino)-3-oxoprop-1-en-2-yl)]sulfonylcarbamate (1447236-85-2) → N6,N6-bis(tert-Butoxycarbonyl)-5′-amino-5′-N-(tert-butoxycarbonyl)-5′-N-[(1-benzylquinol-4-on-3-yl)sulfonyl]-5′-deoxy-2′,3′-Oisopropylideneadenosine (1447236-91-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 22 °C / Inert atmosphere

2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1.08 h / 0 - 22 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; sodium hydride; triphenylphosphine; In tetrahydrofuran; mineral oil; 2: |Mitsunobu Displacement;

DOI:10.1021/jo400976f

upstream raw materials:

tert-butyl [2-(2-fluorophenyl)-2-oxoethyl]sulfonylcarbamate

tert-butyl [3-(2-fluorophenyl)-1-((benzylamino)-3-oxoprop-1-en-2-yl)]sulfonylcarbamate

C₁₆H₂₁FN₂O₅S

N⁶,N⁶-bis(tert-butoxycarbonyl)-2',3'-O-isopropylideneadenosine