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

Base Information

• Chemical Name: 3'-β-bromo-5'-O-(tert-butyldiphenylsilyl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)guanosine
• CAS No.: 1586816-10-5
• Molecular Formula: C₃₇H₄₁BrN₆O₇Si
• Molecular Weight: 789.758

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 4 articles about 3'-β-bromo-5'-O-(tert-butyldiphenylsilyl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)guanosine 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: 95.0%

5'-O-(tert-butyldiphenylsilyl)-N2-isobutyryl-2'-O-(o-nitrobenzyl)-3'-O-trifluoromethylsulfonylguanosine (1586816-09-2) → 3'-β-bromo-5'-O-(tert-butyldiphenylsilyl)-N2-isobutyryl-2'-O-(o-nitrobenzyl)guanosine (1586816-10-5)

Guidance literature:

With sodium bromide; In acetone; for 23h; Reflux; Inert atmosphere;

DOI:10.1021/jo4028374

Reference yield:

N2-isobutyryl-2'-O-(o-nitrobenzyl)guanosine (64350-25-0) → 3'-β-bromo-5'-O-(tert-butyldiphenylsilyl)-N2-isobutyryl-2'-O-(o-nitrobenzyl)guanosine (1586816-10-5)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: sodium bromide / acetone / 23 h / Reflux; Inert atmosphere

With dmap; sodium hydride; sodium bromide; In pyridine; dichloromethane; acetone;

DOI:10.1021/jo4028374

Reference yield:

2-nitrophenylmethyl bromide (3958-60-9) → 3'-β-bromo-5'-O-(tert-butyldiphenylsilyl)-N2-isobutyryl-2'-O-(o-nitrobenzyl)guanosine (1586816-10-5)

Guidance literature:

Multi-step reaction with 4 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

4: sodium bromide / acetone / 23 h / Reflux; Inert atmosphere

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

DOI:10.1021/jo4028374

upstream raw materials:

N²-isobutyryl-2'-deoxyguanosine

2-nitrophenylmethyl bromide

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

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

Downstream raw materials:

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

5'-O-(dimethoxytrityl)-N²-isobutyryl-2'-O-(o-nitrobenzyl)-3'-thioguanosine-3'-S-(cyanoethyl-N,N-diisopropylphosphoramidite)

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