5'-O-(tert-butyldiphenylsilyl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine

Base Information

• Chemical Name: 5'-O-(tert-butyldiphenylsilyl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine
• CAS No.: 1586816-16-1
• Molecular Formula: C₃₇H₄₂N₆O₈Si
• Molecular Weight: 726.861

Synonyms:5'-O-(tert-butyldiphenylsilyl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine

Chemical Property of 5'-O-(tert-butyldiphenylsilyl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine

Chemical Property:

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Technology Process of 5'-O-(tert-butyldiphenylsilyl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine

There total 3 articles about 5'-O-(tert-butyldiphenylsilyl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine 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: 94.0%

N2-isobutyryl-2'-O-(o-nitrobenzyl)guanosine (64350-25-0) + tert-butylchlorodiphenylsilane (58479-61-1) → 5'-O-(tert-butyldiphenylsilyl)-N2-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine (1586816-16-1)

Guidance literature:

With sodium hydride; In pyridine; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jo4028374

Reference yield:

N2-isobutyryl-2'-deoxyguanosine (64350-24-9) → 5'-O-(tert-butyldiphenylsilyl)-N2-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine (1586816-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere

2: sodium hydride / pyridine / 24 h / 20 °C / Inert atmosphere

With sodium hydride; In pyridine; N,N-dimethyl-formamide;

DOI:10.1021/jo4028374

Reference yield:

2-nitrophenylmethyl bromide (3958-60-9) → 5'-O-(tert-butyldiphenylsilyl)-N2-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine (1586816-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere

2: sodium hydride / pyridine / 24 h / 20 °C / Inert atmosphere

With sodium hydride; In pyridine; N,N-dimethyl-formamide;

DOI:10.1021/jo4028374

upstream raw materials:

N²-isobutyryl-2'-deoxyguanosine

2-nitrophenylmethyl bromide

N²-isobutyryl-2'-O-(o-nitrobenzyl)guanosine

tert-butylchlorodiphenylsilane

Downstream raw materials:

5'-O-(tert-butyldiphenylsilyl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine

3'-S-acetyl-N²-isobutyryl-2'-O-(o-nitrobenzyl)-3'-thioguanosine

3'-S-acetyl-5'-O-(dimethoxytrityl)-N²-isobutyryl-2′-O-(onitrobenzyl)-3′-thioguanosine

5'-O-(dimethoxytrityl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)-3'-thioguanosine

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