N⁶-(4,4'-dimethoxytrityl)-9-(2-deoxy-3-O-mesyl-5-O-trityl-β-D-threo-pentofuranosyl)adenine

Base Information

• Chemical Name: N⁶-(4,4'-dimethoxytrityl)-9-(2-deoxy-3-O-mesyl-5-O-trityl-β-D-threo-pentofuranosyl)adenine
• CAS No.: 124040-46-6
• Molecular Formula: C₅₁H₄₇N₅O₇S
• Molecular Weight: 874.029

Synonyms:N⁶-(4,4'-dimethoxytrityl)-9-(2-deoxy-3-O-mesyl-5-O-trityl-β-D-threo-pentofuranosyl)adenine

Chemical Property of N⁶-(4,4'-dimethoxytrityl)-9-(2-deoxy-3-O-mesyl-5-O-trityl-β-D-threo-pentofuranosyl)adenine

Chemical Property:

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Technology Process of N⁶-(4,4'-dimethoxytrityl)-9-(2-deoxy-3-O-mesyl-5-O-trityl-β-D-threo-pentofuranosyl)adenine

There total 5 articles about N⁶-(4,4'-dimethoxytrityl)-9-(2-deoxy-3-O-mesyl-5-O-trityl-β-D-threo-pentofuranosyl)adenine 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: 96.0%

methanesulfonyl chloride (124-63-0) + N6-(4,4'-dimethoxytrityl)-9-(2-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)adenine (124040-45-5) → N6-(4,4'-dimethoxytrityl)-9-(2-deoxy-3-O-mesyl-5-O-trityl-β-D-threo-pentofuranosyl)adenine (124040-46-6)

Guidance literature:

With pyridine; for 4.5h; Ambient temperature;

DOI:10.1016/0008-6215(89)84088-1

Reference yield:

2',3'-O-(dibutylstannylene)adenosine (42822-80-0) → N6-(4,4'-dimethoxytrityl)-9-(2-deoxy-3-O-mesyl-5-O-trityl-β-D-threo-pentofuranosyl)adenine (124040-46-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / Et₃N / methanol; dioxane / Ambient temperature

2: 55 percent / pyridine / dimethylformamide / 1.) RT; 2.) 85 deg C, 4 h

3: 73 percent / LiEt₃BH / tetrahydrofuran / 1.) 5 deg C, 4 h; 2.) RT, 3.5 h

4: 82 percent / pyridine / Ambient temperature

5: 96 percent / pyridine / 4.5 h / Ambient temperature

With pyridine; lithium triethylborohydride; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(89)84088-1

Reference yield:

2'-O-(p-toluenesulfonyl)-5'-O-(triphenylmethyl)adenosine (87412-04-2) → N6-(4,4'-dimethoxytrityl)-9-(2-deoxy-3-O-mesyl-5-O-trityl-β-D-threo-pentofuranosyl)adenine (124040-46-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / LiEt₃BH / tetrahydrofuran / 1.) 5 deg C, 4 h; 2.) RT, 3.5 h

2: 82 percent / pyridine / Ambient temperature

3: 96 percent / pyridine / 4.5 h / Ambient temperature

With pyridine; lithium triethylborohydride; In tetrahydrofuran;

DOI:10.1016/0008-6215(89)84088-1

upstream raw materials:

methanesulfonyl chloride

N⁶-(4,4'-dimethoxytrityl)-9-(2-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)adenine

2',3'-O-(dibutylstannylene)adenosine

4,4'-dimethoxytrityl chloride

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