3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N⁶,N⁶-dimethyladenosine

Base Information

• Chemical Name: 3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N⁶,N⁶-dimethyladenosine
• CAS No.: 699021-37-9
• Molecular Formula: C₂₇H₄₀N₆O₅Si
• Molecular Weight: 556.737

Synonyms:3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N⁶,N⁶-dimethyladenosine

Chemical Property of 3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N⁶,N⁶-dimethyladenosine

Chemical Property:

Purity/Quality:

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Technology Process of 3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N⁶,N⁶-dimethyladenosine

There total 1 articles about 3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N⁶,N⁶-dimethyladenosine 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: 82.0%

(2S)-2-(tert-butyldimethylsilyloxy)-3-phenylpropanoyl chloride (143417-86-1) + 3'-amino-3'-deoxy-N6,N6-dimethyladenosine (58-60-6) → 3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N6,N6-dimethyladenosine (699021-37-9)

Guidance literature:

3'-amino-3'-deoxy-N⁶,N⁶-dimethyladenosine; With pyridine; chloro-trimethyl-silane; at 0 - 20 ℃; for 2h;

(2S)-2-(tert-butyldimethylsilyloxy)-3-phenylpropanoyl chloride; In dichloromethane; at 0 - 20 ℃; for 2h;

With potassium carbonate; for 1h;

DOI:10.1021/ja0554099

Reference yield: 66.0%

3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N6,N6-dimethyladenosine (699021-37-9) + 4,4'-dimethoxytrityl chloride (40615-36-9) → (S)-N-[(2S,3S,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-tetrahydro-furan-3-yl]-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionamide (882688-77-9)

Guidance literature:

With pyridine; at 20 ℃; for 17h;

DOI:10.1021/ja0554099

Reference yield:

3'N-[[(2S)-2-tert-butyldimethylsilyloxy-3-phenyl-1-oxopropyl]amino]-3'-deoxy-N6,N6-dimethyladenosine (699021-37-9) → Succinic acid mono-[(2R,3R,4R,5S)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionylamino]-2-(6-dimethylamino-purin-9-yl)-tetrahydro-furan-3-yl] ester

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / pyridine / 17 h / 20 °C

2: 50 percent / pyridine; DMAP / 24 h / 20 °C

With pyridine; dmap;

DOI:10.1021/ja0554099

upstream raw materials:

(2S)-2-(tert-butyldimethylsilyloxy)-3-phenylpropanoyl chloride

3'-amino-3'-deoxy-N⁶,N⁶-dimethyladenosine

Downstream raw materials:

(S)-N-[(2S,3S,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-tetrahydro-furan-3-yl]-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionamide

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