Adenosine, 2'-O-[(1,1-dimethylethyl)dimethylsilyl]-

Base Information

• Chemical Name: Adenosine, 2'-O-[(1,1-dimethylethyl)dimethylsilyl]-
• CAS No.: 69504-13-8
• Molecular Formula: C16H27N5O4Si
• Molecular Weight: 381.50200
• DSSTox Substance ID: DTXSID30572907
• Nikkaji Number: J1.400.946I
• Wikidata: Q82461419
• Mol file: 69504-13-8.mol

Synonyms:69504-13-8;Adenosine, 2'-O-[(1,1-dimethylethyl)dimethylsilyl]-;(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)tetrahydrofuran-3-ol;(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)oxolan-3-ol;2'-o-tert-butyldimethylsilyladenosine;SCHEMBL7893460;DTXSID30572907;2'-O-[tert-Butyl(dimethyl)silyl]adenosine

Chemical Property of Adenosine, 2'-O-[(1,1-dimethylethyl)dimethylsilyl]-

Chemical Property:

• PSA: 128.54000
• LogP: 1.63070
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 381.18323089
• Heavy Atom Count: 26
• Complexity: 506

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1C(C(OC1N2C=NC3=C(N=CN=C32)N)CO)O
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)N)CO)O

Technology Process of Adenosine, 2'-O-[(1,1-dimethylethyl)dimethylsilyl]-

There total 5 articles about Adenosine, 2'-O-[(1,1-dimethylethyl)dimethylsilyl]- 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: 95.0%

9-[2-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl]adenine (124583-06-8) → 2'-O-(tert-butyldimethylsilyl)adenosine (69504-13-8)

Guidance literature:

With sodium tetrahydroborate; acetic acid; for 2h; Ambient temperature;

DOI:10.1021/jo00289a004

Reference yield: 90.0%

2',5'-bis-O-(tert-butyldimethylsilyl)adenosine (65109-11-7) → 2'-O-(tert-butyldimethylsilyl)adenosine (69504-13-8)

Guidance literature:

With ammonium cerium(IV) nitrate; silica gel; In tetrachloromethane; isopropyl alcohol; for 7h; Heating;

DOI:10.1021/jo000024o

Reference yield:

9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine (86734-95-4) → 2'-O-(tert-butyldimethylsilyl)adenosine (69504-13-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / trifluoroacetic acid, water / 0 °C

2: 95 percent / NaBH₄, AcOH / 2 h / Ambient temperature

With sodium tetrahydroborate; water; acetic acid; trifluoroacetic acid;

DOI:10.1021/jo00289a004

upstream raw materials:

3'-O-(tert-butyldimethylsilyl)adenosine

9-[2-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl]adenine

2',5'-bis-O-(tert-butyldimethylsilyl)adenosine

9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine

Downstream raw materials:

3'-O-(tert-butyldimethylsilyl)adenosine