5'-O-t-butyldiphenylsilyl-3'-deoxy-3'-iodo-2',3'-secoadenosine 2'-(phenyl methylphosphonate)

Base Information

• Chemical Name: 5'-O-t-butyldiphenylsilyl-3'-deoxy-3'-iodo-2',3'-secoadenosine 2'-(phenyl methylphosphonate)
• CAS No.: 119898-77-0
• Molecular Formula: C₃₃H₃₉IN₅O₅PSi
• Molecular Weight: 771.667
• Mol file: 119898-77-0.mol

Synonyms:

Chemical Property of 5'-O-t-butyldiphenylsilyl-3'-deoxy-3'-iodo-2',3'-secoadenosine 2'-(phenyl methylphosphonate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-t-butyldiphenylsilyl-3'-deoxy-3'-iodo-2',3'-secoadenosine 2'-(phenyl methylphosphonate)

There total 5 articles about 5'-O-t-butyldiphenylsilyl-3'-deoxy-3'-iodo-2',3'-secoadenosine 2'-(phenyl methylphosphonate) 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: 43.0%

5'-O-t-butyldiphenylsilyl-2',3'-secoadenosine (119898-69-0) → 5'-O-t-butyldiphenylsilyl-2',3'-dideoxy-2',3'-diiodo-2',3'-secoadenosine (119923-12-5) + 5'-O-t-butyldiphenylsilyl-3'-deoxy-3'-iodo-2',3'-secoadenosine 2'-(phenyl methylphosphonate) (119898-77-0)

Guidance literature:

With methyl-triphenylphosphonium iodide; In N,N-dimethyl-formamide; for 0.0833333h;

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) → 5'-O-t-butyldiphenylsilyl-3'-deoxy-3'-iodo-2',3'-secoadenosine 2'-(phenyl methylphosphonate) (119898-77-0)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 40 percent / dimethylformamide / 0.08 h

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

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

Reference yield:

5'-O-t-butyldiphenylsilyladenosine dialdehyde (119898-67-8) → 5'-O-t-butyldiphenylsilyl-3'-deoxy-3'-iodo-2',3'-secoadenosine 2'-(phenyl methylphosphonate) (119898-77-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / sodium borohydride / ethanol; H₂O / Ambient temperature; dark

2: 40 percent / dimethylformamide / 0.08 h

With sodium tetrahydroborate; In ethanol; water; N,N-dimethyl-formamide;

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

upstream raw materials:

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

tert-butylchlorodiphenylsilane