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

Base Information

• Chemical Name: 3'-S-acetyl-5'-O-(dimethoxytrityl)-N²-isobutyryl-2′-O-(onitrobenzyl)-3′-thioguanosine
• CAS No.: 1586816-12-7
• Molecular Formula: C₄₄H₄₄N₆O₁₀S
• Molecular Weight: 848.934

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

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

Chemical Property:

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

There total 8 articles about 3'-S-acetyl-5'-O-(dimethoxytrityl)-N²-isobutyryl-2′-O-(onitrobenzyl)-3′-thioguanosine 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%

4,4'-dimethoxytrityl chloride (40615-36-9) + 3'-S-acetyl-N2-isobutyryl-2'-O-(o-nitrobenzyl)-3'-thioguanosine (1586816-11-6) → 3'-S-acetyl-5'-O-(dimethoxytrityl)-N2-isobutyryl-2′-O-(onitrobenzyl)-3′-thioguanosine (1586816-12-7)

Guidance literature:

In pyridine; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jo4028374

Reference yield:

3'-S-acetyl-N2-isobutyryl-2'-O-(o-nitrobenzyl)-3'-thioguanosine → 3'-S-acetyl-5'-O-(dimethoxytrityl)-N2-isobutyryl-2′-O-(onitrobenzyl)-3′-thioguanosine (1586816-12-7)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; tetra-n-butylammoniumfluoride trihydrate / 14 h / 20 °C

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

With acetic acid; tetra-n-butylammoniumfluoride trihydrate; In pyridine;

DOI:10.1021/jo4028374

Reference yield:

N2-isobutyryl-2'-O-(o-nitrobenzyl)guanosine (64350-25-0) → 3'-S-acetyl-5'-O-(dimethoxytrityl)-N2-isobutyryl-2′-O-(onitrobenzyl)-3′-thioguanosine (1586816-12-7)

Guidance literature:

Multi-step reaction with 6 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

4: N,N-dimethyl-formamide / 7 h / 60 °C / Inert atmosphere

5: acetic acid; tetra-n-butylammoniumfluoride trihydrate / 14 h / 20 °C

6: pyridine / 24 h / 20 °C / Inert atmosphere

With dmap; sodium hydride; acetic acid; tetra-n-butylammoniumfluoride trihydrate; 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

4,4'-dimethoxytrityl chloride

Downstream raw materials:

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

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