3'-O-(tert-Butyldimethylsilyl)-2'-deoxyadenosine

Base Information

• Chemical Name: 3'-O-(tert-Butyldimethylsilyl)-2'-deoxyadenosine
• CAS No.: 51549-31-6
• Molecular Formula: C16H27N5O3Si
• Molecular Weight: 365.508
• DSSTox Substance ID: DTXSID40449858
• Nikkaji Number: J518.331F
• Wikidata: Q82269394
• Mol file: 51549-31-6.mol

Synonyms:51549-31-6;3'-O-(tert-Butyldimethylsilyl)-2'-deoxyadenosine;[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-[tert-butyl(dimethyl)silyl]oxyoxolan-2-yl]methanol;((2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methanol;C16H27N5O3Si;SCHEMBL9548819;DTXSID40449858;Adenosine, 2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-;CS-D0252;D77324

Chemical Property of 3'-O-(tert-Butyldimethylsilyl)-2'-deoxyadenosine

Chemical Property:

• PSA: 108.31000
• LogP: 2.65990
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 365.18831627
• Heavy Atom Count: 25
• Complexity: 475

Purity/Quality:

97% ^*data from raw suppliers

3'-O-(tert-butyldiMethylsilyl)-2'-deoxyadenosine ≥98.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1CC(OC1CO)N2C=NC3=C(N=CN=C32)N
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@H]1C[C@@H](O[C@@H]1CO)N2C=NC3=C(N=CN=C32)N

Technology Process of 3'-O-(tert-Butyldimethylsilyl)-2'-deoxyadenosine

There total 11 articles about 3'-O-(tert-Butyldimethylsilyl)-2'-deoxyadenosine 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: 80.0%

5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine (89947-86-4) → 3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine (51549-31-6)

Guidance literature:

With iodine; In methanol; at 60 ℃;

DOI:10.1021/jo972222u

Reference yield: 80.0%

3',5'-bis-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine (51549-32-7) → 3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine (51549-31-6)

Guidance literature:

With acetic acid; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2005.05.035

Reference yield: 41.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 2'-deoxy-D-adenosine (958-09-8,7005-15-4) → 3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine (51549-31-6)

Guidance literature:

tert-butyldimethylsilyl chloride; 2'-deoxy-D-adenosine; With pyridine; 1H-imidazole; at 20 ℃; Cooling with ice;

With ammonium hydroxide; trifluoroacetic acid; In tetrahydrofuran; water;

DOI:10.1016/j.bmcl.2008.07.015

upstream raw materials:

3'-O-TBDMS-5'-O-TBDPS-2'-deoxyadenosine

5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine

3',5'-bis-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine

8-bromo-O₃'-(tert-butyldimethylsilyl)-2'-deoxyadenosine

Downstream raw materials:

3'-O-tert-butyldimethylsilyldeoxyadenosine 5'-[ethyl N-(N-trityl-L-prolyl)phosphoroamidate]

(E)-3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylprop-2-en-1-one

6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine

6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite)