N⁶-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethyladenosine

Base Information

• Chemical Name: N⁶-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethyladenosine
• CAS No.: 260269-31-6
• Molecular Formula: C₄₅H₄₇N₅O₁₀SSi
• Molecular Weight: 878.047

Synonyms:N⁶-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethyladenosine

Chemical Property of N⁶-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethyladenosine

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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MSDS Files:

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Technology Process of N⁶-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethyladenosine

There total 10 articles about N⁶-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethyladenosine 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: 70.0%

N-Benzoyl-N,9-bis(trimethylsilyl)adenin (18055-47-5) + Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester (260269-28-1) → N6-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethyladenosine (260269-31-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; Heating;

DOI:10.1039/a907218g

Reference yield: 70.0%

N-Benzoyl-N,9-bis(trimethylsilyl)adenin (18055-47-5) + 5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose (446862-76-6) → N6-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethyladenosine (260269-31-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 23h; Heating;

DOI:10.1016/S0040-4020(02)00227-2

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → N6-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethyladenosine (260269-31-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 67 percent / CH₂Cl₂ / 11 h / 20 °C

2.1: 97 percent / 4,4-dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

3.1: conc. H₂SO₄ / acetic acid / 2 h / 20 °C

3.2: H₂ / 10 percent Pd/C / ethyl acetate; CHCl₃ / 16 h / 20 °C

3.3: pyridine / 49 h / 20 °C

4.1: 70 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 23 h / Heating

With dmap; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; In dichloromethane; acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(02)00227-2

upstream raw materials:

N-Benzoyl-N,9-bis(trimethylsilyl)adenin

Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose

p-toluenesulfonyl chloride

Downstream raw materials:

N⁶-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methyleneadenosine

N⁶-benzoyl-5'-O-tert-butyldiphenylsilyl-4'-C-(p-toluenesulfonyl)oxymethyladenosine

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