Adenosine, 5'-O-((1,1-dimethylethyl)dimethylsilyl)-, 2'-(4-methylbenzenesulfonate

Base Information

• Chemical Name: Adenosine, 5'-O-((1,1-dimethylethyl)dimethylsilyl)-, 2'-(4-methylbenzenesulfonate
• CAS No.: 115094-43-4
• Molecular Formula: C23H33N5O6SSi
• Molecular Weight: 535.69
• Nikkaji Number: J352.818I
• Mol file: 115094-43-4.mol

Synonyms:115094-43-4;Adenosine, 5'-O-((1,1-dimethylethyl)dimethylsilyl)-, 2'-(4-methylbenzenesulfonate;[(2R,3R,4R,5R)-2-(6-Aminopurin-9-yl)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-3-yl] 4-methylbenzenesulfonate

Chemical Property of Adenosine, 5'-O-((1,1-dimethylethyl)dimethylsilyl)-, 2'-(4-methylbenzenesulfonate

Chemical Property:

• PSA: 160.06000
• LogP: 4.43310
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 535.19208150
• Heavy Atom Count: 36
• Complexity: 860

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC2C(C(OC2N3C=NC4=C(N=CN=C43)N)CO[Si](C)(C)C(C)(C)C)O
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O[C@@H]2[C@@H]([C@H](O[C@H]2N3C=NC4=C(N=CN=C43)N)CO[Si](C)(C)C(C)(C)C)O

Technology Process of Adenosine, 5'-O-((1,1-dimethylethyl)dimethylsilyl)-, 2'-(4-methylbenzenesulfonate

There total 8 articles about Adenosine, 5'-O-((1,1-dimethylethyl)dimethylsilyl)-, 2'-(4-methylbenzenesulfonate 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%

6-di-N,N-3'-O-triacetyl-5'-O-tert-butyldimethylsilyl-2'-O-tosyladenosine (863591-95-1) → 5'-O-(tert-butyldimethylsilyl)-2'-O-(p-tolylsulfonyl)adenosine (115094-43-4)

Guidance literature:

In methanol; at 105 ℃; for 1.5h;

DOI:10.1021/jo051256w

Reference yield: 66.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 2'-O-tosyladenosine (42776-78-3) → 5'-O-(tert-butyldimethylsilyl)-2'-O-(p-tolylsulfonyl)adenosine (115094-43-4)

Guidance literature:

With pyridine; Ambient temperature;

DOI:10.1021/ja962117m

Reference yield:

O3',O5'-(1,1,3,3-tetraisopropyl-disiloxane-1,3-diyl)-O2'-(toluene-4-sulfonyl)-adenosine → 5'-O-(tert-butyldimethylsilyl)-2'-O-(p-tolylsulfonyl)adenosine (115094-43-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₄F / methanol / Ambient temperature

2: 66 percent / pyridine / Ambient temperature

With pyridine; ammonium fluoride; In methanol;

DOI:10.1021/ja962117m

upstream raw materials:

5'-(O-tert-butyldimethylsilyl)adenosine

p-toluenesulfonyl chloride

tert-butyldimethylsilyl chloride

2'-O-tosyladenosine

Downstream raw materials:

Toluene-4-sulfonic acid (2R,3R,4R,5R)-2-(6-amino-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-phenoxythiocarbonyloxy-tetrahydro-furan-3-yl ester

6-di-N,N-3'-O-triacetyl-5'-O-tert-butyldimethylsilyl-2'-O-tosyladenosine

Toluene-4-sulfonic acid (2R,3R,5S)-2-(6-amino-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

N-Benzoyl-N-[9-((2R,4S,5R)-4-fluoro-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide