8-bromo-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-(dimethylthexylsilyloxymethyl)cyclopentyl]-5'-O-4,4'-dimethoxytrityl-2',3'-O-isopropylidene-N⁶-trichloroacetyladenosine

Base Information

• Chemical Name: 8-bromo-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-(dimethylthexylsilyloxymethyl)cyclopentyl]-5'-O-4,4'-dimethoxytrityl-2',3'-O-isopropylidene-N⁶-trichloroacetyladenosine
• CAS No.: 268749-29-7
• Molecular Formula: C₅₃H₆₅BrCl₃N₅O₁₀Si
• Molecular Weight: 1146.48

Synonyms:

Chemical Property of 8-bromo-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-(dimethylthexylsilyloxymethyl)cyclopentyl]-5'-O-4,4'-dimethoxytrityl-2',3'-O-isopropylidene-N⁶-trichloroacetyladenosine

Chemical Property:

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Useful:

Technology Process of 8-bromo-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-(dimethylthexylsilyloxymethyl)cyclopentyl]-5'-O-4,4'-dimethoxytrityl-2',3'-O-isopropylidene-N⁶-trichloroacetyladenosine

There total 4 articles about 8-bromo-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-(dimethylthexylsilyloxymethyl)cyclopentyl]-5'-O-4,4'-dimethoxytrityl-2',3'-O-isopropylidene-N⁶-trichloroacetyladenosine 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: 17.0%

Trifluoro-methanesulfonic acid (3aR,4S,6R,6aR)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester (189574-99-0) + N-(9-{6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-8-bromo-9H-purin-6-yl)-2,2,2-trichloro-acetamide (268749-28-6) → 8-bromo-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-(dimethylthexylsilyloxymethyl)cyclopentyl]-5'-O-4,4'-dimethoxytrityl-2',3'-O-isopropylidene-N6-trichloroacetyladenosine (268749-29-7)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In 1,2-dimethoxyethane; at 50 ℃; for 21h;

DOI:10.1080/15257770008033002

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 8-bromo-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-(dimethylthexylsilyloxymethyl)cyclopentyl]-5'-O-4,4'-dimethoxytrityl-2',3'-O-isopropylidene-N6-trichloroacetyladenosine (268749-29-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / pyridine / 7 h / 20 °C

2: Et₃N / CH₂Cl₂ / 0.05 h / 0 °C

3: 17 percent / K₂CO₃; 18-crown-6 / 1,2-dimethoxy-ethane / 21 h / 50 °C

With pyridine; 18-crown-6 ether; potassium carbonate; triethylamine; In 1,2-dimethoxyethane; dichloromethane; 1: Substitution / 2: Acylation / 3: Substitution;

DOI:10.1080/15257770008033002

Reference yield:

8-bromo-2',3'-O-isopropylene adenosine (13089-45-7) → 8-bromo-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-(dimethylthexylsilyloxymethyl)cyclopentyl]-5'-O-4,4'-dimethoxytrityl-2',3'-O-isopropylidene-N6-trichloroacetyladenosine (268749-29-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / pyridine / 7 h / 20 °C

2: Et₃N / CH₂Cl₂ / 0.05 h / 0 °C

3: 17 percent / K₂CO₃; 18-crown-6 / 1,2-dimethoxy-ethane / 21 h / 50 °C

With pyridine; 18-crown-6 ether; potassium carbonate; triethylamine; In 1,2-dimethoxyethane; dichloromethane; 1: Substitution / 2: Acylation / 3: Substitution;

DOI:10.1080/15257770008033002

upstream raw materials:

Trifluoro-methanesulfonic acid (3aR,4S,6R,6aR)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester

N-(9-{6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-8-bromo-9H-purin-6-yl)-2,2,2-trichloro-acetamide

4,4'-dimethoxytrityl chloride

8-bromo-2',3'-O-isopropylene adenosine

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