2'-O-acetyl-3'-azido-5'-O-t-butyldiphenylsilyl-3'-deoxy-2',3'-secoadenosine

Base Information

• Chemical Name: 2'-O-acetyl-3'-azido-5'-O-t-butyldiphenylsilyl-3'-deoxy-2',3'-secoadenosine
• CAS No.: 119898-82-7
• Molecular Formula: C₂₈H₃₄N₈O₄Si
• Molecular Weight: 574.715
• Mol file: 119898-82-7.mol

Synonyms:2'-O-acetyl-3'-azido-5'-O-t-butyldiphenylsilyl-3'-deoxy-2',3'-secoadenosine

Chemical Property of 2'-O-acetyl-3'-azido-5'-O-t-butyldiphenylsilyl-3'-deoxy-2',3'-secoadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-acetyl-3'-azido-5'-O-t-butyldiphenylsilyl-3'-deoxy-2',3'-secoadenosine

There total 7 articles about 2'-O-acetyl-3'-azido-5'-O-t-butyldiphenylsilyl-3'-deoxy-2',3'-secoadenosine 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: 96.0%

3'-azido-5'-O-t-butyldiphenylsilyl-3'-deoxy-2'-O-mesyl-2',3'-secoadenosine (119898-80-5) → 2'-O-acetyl-3'-azido-5'-O-t-butyldiphenylsilyl-3'-deoxy-2',3'-secoadenosine (119898-82-7)

Guidance literature:

In N,N-dimethyl-formamide; at 95 ℃; for 48h;

DOI:10.1016/S0040-4020(01)89829-X

Reference yield:

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3,4-diol (119898-65-6) → 2'-O-acetyl-3'-azido-5'-O-t-butyldiphenylsilyl-3'-deoxy-2',3'-secoadenosine (119898-82-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / sodium periodate / acetone; H₂O / 15 °C / dark

2: 83 percent / sodium borohydride / ethanol; H₂O / Ambient temperature; dark

3: 80 percent / pyridine / 0 °C

4: 66 percent / lithium azide / dimethylformamide / 48 h / 55 - 60 °C

5: 96 percent / dimethylformamide / 48 h / 95 °C

With sodium tetrahydroborate; sodium periodate; lithium azide; In pyridine; ethanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)89829-X

Reference yield:

5'-O-t-butyldiphenylsilyl-2',3'-secoadenosine (119898-69-0) → 2'-O-acetyl-3'-azido-5'-O-t-butyldiphenylsilyl-3'-deoxy-2',3'-secoadenosine (119898-82-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / pyridine / 0 °C

2: 66 percent / lithium azide / dimethylformamide / 48 h / 55 - 60 °C

3: 96 percent / dimethylformamide / 48 h / 95 °C

With lithium azide; In pyridine; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)89829-X

upstream raw materials:

3'-azido-5'-O-t-butyldiphenylsilyl-3'-deoxy-2'-O-mesyl-2',3'-secoadenosine

5'-O-t-butyldiphenylsilyl-2',3'-secoadenosine

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3,4-diol

5'-O-t-butyldiphenylsilyladenosine dialdehyde

Downstream raw materials:

3'-N-(N'-benzyloxycarbonyl-L-phenylalanyl)-3'-deoxy-2',3'-secoadenosine

3'-deoxy-3'-N-L-phenylalanyl-2',3'-secoadenosine

3'-azido-5'-O-t-butyldiphenylsilyl-3'-deoxy-2',3'-secoadenosine