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.: 1586816-09-2
• Molecular Formula: C₃₈H₄₁F₃N₆O₁₀SSi
• Molecular Weight: 858.924

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:

Purity/Quality:

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

There total 4 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: 62.0%

trifluoromethane sulfonyl chloride (421-83-0) + 5'-O-(tert-butyldiphenylsilyl)-N2-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine (1586816-16-1) → 5'-O-(tert-butyldiphenylsilyl)-N2-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine (1586816-09-2)

Guidance literature:

With dmap; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1021/jo4028374

Reference yield:

N2-isobutyryl-2'-O-(o-nitrobenzyl)guanosine (64350-25-0) → 5'-O-(tert-butyldiphenylsilyl)-N2-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine (1586816-09-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: dmap / dichloromethane / 3 h / 0 °C

With dmap; sodium hydride; In pyridine; dichloromethane;

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 (1586816-09-2)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: dmap / dichloromethane / 3 h / 0 °C

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

DOI:10.1021/jo4028374

upstream raw materials:

N²-isobutyryl-2'-deoxyguanosine

2-nitrophenylmethyl bromide

trifluoromethane sulfonyl chloride

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

Downstream raw materials:

3'-β-bromo-5'-O-(tert-butyldiphenylsilyl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)guanosine

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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