N⁶-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-{2-[(methyleneamino)oxy]ethyl}adenosine

Base Information

• Chemical Name: N⁶-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-{2-[(methyleneamino)oxy]ethyl}adenosine
• CAS No.: 212061-63-7
• Molecular Formula: C₃₆H₄₀N₆O₆Si
• Molecular Weight: 680.836

Synonyms:N⁶-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-{2-[(methyleneamino)oxy]ethyl}adenosine

Chemical Property of N⁶-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-{2-[(methyleneamino)oxy]ethyl}adenosine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-{2-[(methyleneamino)oxy]ethyl}adenosine

There total 8 articles about N⁶-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-{2-[(methyleneamino)oxy]ethyl}adenosine 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:

benzoyl chloride (98-88-4) → N6-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-{2-[(methyleneamino)oxy]ethyl}adenosine (212061-63-7)

Guidance literature:

Multi-step reaction with 7 steps

1: N-methylmorpholine N-oxide; OsO₄ / dioxane / 3 h

2: NaIO₄ on SiO₂ / CH₂Cl₂ / 0.5 h / 20 °C

3: 4.31 g / pyridinium p-toluenesulfonate; NaBH₃CN / methanol / 8 h / 20 °C

4: 91.5 percent / PPh₃; DEAD / tetrahydrofuran / 20 °C

5: N-methylhydrazine / CH₂Cl₂ / 0 °C

6: 2.47 g / methanol; H₂O / 20 °C

With sodium periodate; osmium(VIII) oxide; pyridinium p-toluenesulfonate; sodium cyanoborohydride; 4-methylmorpholine N-oxide; triphenylphosphine; methylhydrazine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 5: Mitsunobu reaction;

DOI:10.1021/jo0103975

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → N6-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-{2-[(methyleneamino)oxy]ethyl}adenosine (212061-63-7)

Guidance literature:

Multi-step reaction with 7 steps

1: N-methylmorpholine N-oxide; OsO₄ / dioxane / 3 h

2: NaIO₄ on SiO₂ / CH₂Cl₂ / 0.5 h / 20 °C

3: 4.31 g / pyridinium p-toluenesulfonate; NaBH₃CN / methanol / 8 h / 20 °C

4: 91.5 percent / PPh₃; DEAD / tetrahydrofuran / 20 °C

5: N-methylhydrazine / CH₂Cl₂ / 0 °C

6: 2.47 g / methanol; H₂O / 20 °C

With sodium periodate; osmium(VIII) oxide; pyridinium p-toluenesulfonate; sodium cyanoborohydride; 4-methylmorpholine N-oxide; triphenylphosphine; methylhydrazine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 5: Mitsunobu reaction;

DOI:10.1021/jo0103975

Reference yield:

N-{9-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-(2-oxo-ethoxy)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide (212061-32-0) → N6-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-{2-[(methyleneamino)oxy]ethyl}adenosine (212061-63-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 4.31 g / pyridinium p-toluenesulfonate; NaBH₃CN / methanol / 8 h / 20 °C

2: 91.5 percent / PPh₃; DEAD / tetrahydrofuran / 20 °C

3: N-methylhydrazine / CH₂Cl₂ / 0 °C

4: 2.47 g / methanol; H₂O / 20 °C

With pyridinium p-toluenesulfonate; sodium cyanoborohydride; triphenylphosphine; methylhydrazine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; 2: Mitsunobu reaction;

DOI:10.1021/jo0103975

upstream raw materials:

benzoyl chloride

tert-butylchlorodiphenylsilane

N-{9-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-(2-oxo-ethoxy)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide

2'-O-allyl-N⁶-benzoyl-5'-O-(tert-butyldiphenylsilyl)adenosine

Downstream raw materials:

N⁶-benzoyl-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}adenosine

N⁶-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}adenosine

N-(9-{5-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-[2-(N-methyl-aminooxy)-ethoxy]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide

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