2'-deoxy-2'-methyleneadenosine

Base Information

• Chemical Name: 2'-deoxy-2'-methyleneadenosine
• CAS No.: 104409-41-8
• Molecular Formula: C₁₁H₁₃N₅O₃
• Molecular Weight: 263.256
• Mol file: 104409-41-8.mol

Synonyms:2'-Deoxy-2'-methyleneadenosine

Chemical Property of 2'-deoxy-2'-methyleneadenosine

Chemical Property:

• Boiling Point: 617.5°Cat760mmHg
• Flash Point: 327.3°C
• PSA: 119.31000
• Density: 1.8g/cm³
• LogP: -0.20350

Purity/Quality:

97% ^*data from raw suppliers

2'-Deoxy-2'-methyleneadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2'-deoxy-2'-methyleneadenosine

There total 5 articles about 2'-deoxy-2'-methyleneadenosine 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: 99.0%

9-(3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-2-methylene-β-D-erythro-pentofuranosyl)adenine (137058-78-7) → 2'-deoxy-2'-methyleneadenosine (104409-41-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h;

DOI:10.1021/jo00025a029

Reference yield: 87.3%

9-(2-deoxy-3,5-O-(tetraisopropyldisiloxanediyl)-2-methylene-β-D-erythro-pentofuranosyl)adenine (104409-40-7) → 2'-deoxy-2'-methyleneadenosine (104409-41-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.25h;

DOI:10.1248/cpb.34.1518

Reference yield:

3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine (69504-03-6) → 2'-deoxy-2'-methyleneadenosine (104409-41-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / CrO₃, pyridine, Ac₂O / CH₂Cl₂

2: 1) sodium 2-methyl-2-butoxide / 1) Et₂O, benzene, 2h, 2a) -70 to -10 deg C, 1h, 2b) 4 deg C, 48h

3: 99 percent / Bu₄NF / tetrahydrofuran / 3 h

With pyridine; chromium(VI) oxide; tetrabutyl ammonium fluoride; acetic anhydride; sodium tert-pentoxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00025a029

upstream raw materials:

9-(3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-2-methylene-β-D-erythro-pentofuranosyl)adenine

9-(2-deoxy-3,5-O-(tetraisopropyldisiloxanediyl)-2-methylene-β-D-erythro-pentofuranosyl)adenine

3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine

9-(3,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-2-ulosyl)adenine

Downstream raw materials:

9-(2-deoxy-2-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine

C₂₅H₂₅N₅O₇S₂

9-(5-O-(tert-Butyldiphenylsilyl)-2-deoxy-2-methylene-β-D-erythro-pentofuranosyl)adenine

6-N,N-dibenzoyl-9-(3-O-(tert-butyldimethylsilyl)-2-deoxy-2-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine