2'-O-[(tert-butyl)dimetylsilyl]-5'-O-(4,4'-dimethoxytrityl)-N²-isobutyryl-3'-S-(pyridin-2-ylthio)-3'-thioguanosine

Base Information

• Chemical Name: 2'-O-[(tert-butyl)dimetylsilyl]-5'-O-(4,4'-dimethoxytrityl)-N²-isobutyryl-3'-S-(pyridin-2-ylthio)-3'-thioguanosine
• CAS No.: 247223-70-7
• Molecular Formula: C₄₆H₅₄N₆O₇S₂Si
• Molecular Weight: 895.188

Synonyms:2'-O-[(tert-butyl)dimetylsilyl]-5'-O-(4,4'-dimethoxytrityl)-N²-isobutyryl-3'-S-(pyridin-2-ylthio)-3'-thioguanosine

Chemical Property of 2'-O-[(tert-butyl)dimetylsilyl]-5'-O-(4,4'-dimethoxytrityl)-N²-isobutyryl-3'-S-(pyridin-2-ylthio)-3'-thioguanosine

Chemical Property:

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Technology Process of 2'-O-[(tert-butyl)dimetylsilyl]-5'-O-(4,4'-dimethoxytrityl)-N²-isobutyryl-3'-S-(pyridin-2-ylthio)-3'-thioguanosine

There total 15 articles about 2'-O-[(tert-butyl)dimetylsilyl]-5'-O-(4,4'-dimethoxytrityl)-N²-isobutyryl-3'-S-(pyridin-2-ylthio)-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%

2-Methylpropionic anhydride (97-72-3) + 2'-O-[(tert-butyl)dimetylsilyl]-5'-O-(4,4'-dimethoxytrityl)-3'-S-(pyridin-2-ylthio)-3'-thioguanosine (247223-69-4) → 2'-O-[(tert-butyl)dimetylsilyl]-5'-O-(4,4'-dimethoxytrityl)-N2-isobutyryl-3'-S-(pyridin-2-ylthio)-3'-thioguanosine (247223-70-7)

Guidance literature:

With dmap; In pyridine; at 20 - 50 ℃; for 21h;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2141::AID-HLCA2141>3.0.CO;2-2

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 2'-O-[(tert-butyl)dimetylsilyl]-5'-O-(4,4'-dimethoxytrityl)-N2-isobutyryl-3'-S-(pyridin-2-ylthio)-3'-thioguanosine (247223-70-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / pyridine / 4 h / 20 °C

2: MeNH₂ / H₂O / 16 h / 20 °C

3: dimethylformamide / 10 h / 60 °C

4: 85 percent / 1H-imidazole / pyridine / 16 h / 20 °C

5: 95 percent / 4-(dimethylamino)pyridine / pyridine / 21 h / 20 - 50 °C

With 1H-imidazole; dmap; methylamine; In pyridine; water; N,N-dimethyl-formamide; 1: Etherification / 2: Hydrolysis / 3: Substitution / 4: Silylation / 5: Acylation;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2141::AID-HLCA2141>3.0.CO;2-2

Reference yield:

N2-[(dimethylamino)methylene]guanosine (1055407-32-3) → 2'-O-[(tert-butyl)dimetylsilyl]-5'-O-(4,4'-dimethoxytrityl)-N2-isobutyryl-3'-S-(pyridin-2-ylthio)-3'-thioguanosine (247223-70-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 96 percent / pyridine / 16 h / 20 °C

2.1: 87 percent / H₂O; acetonitrile / 3 h / 20 °C

3.1: dimethylformamide / 16 h / 60 °C

3.2: 46 percent / Bu₄NF*3H₂O; AcOH / tetrahydrofuran / 5 h / 20 °C

4.1: 70 percent / pyridine / 4 h / 20 °C

5.1: MeNH₂ / H₂O / 16 h / 20 °C

6.1: dimethylformamide / 10 h / 60 °C

7.1: 85 percent / 1H-imidazole / pyridine / 16 h / 20 °C

8.1: 95 percent / 4-(dimethylamino)pyridine / pyridine / 21 h / 20 - 50 °C

With 1H-imidazole; dmap; methylamine; In pyridine; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Silylation / 2.1: Acetylation / 3.1: Elimination / 3.2: Hydrolysis / 4.1: Etherification / 5.1: Hydrolysis / 6.1: Substitution / 7.1: Silylation / 8.1: Acylation;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2141::AID-HLCA2141>3.0.CO;2-2

upstream raw materials:

2-Methylpropionic anhydride

2'-O-[(tert-butyl)dimetylsilyl]-5'-O-(4,4'-dimethoxytrityl)-3'-S-(pyridin-2-ylthio)-3'-thioguanosine

2,2'-dipyridyldisulphide

4,4'-dimethoxytrityl chloride

Downstream raw materials:

2'-O-[(tert-butyl)dimetylsilyl]-5'-O-(4,4'-dimethoxytrityl)-N²-isobutyryl-3'-thioguanosine

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