5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-fluoro-3'-deoxyadenosine

Base Information

• Chemical Name: 5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-fluoro-3'-deoxyadenosine
• CAS No.: 131372-54-8
• Molecular Formula: C₃₆H₄₂FN₅O₄Si
• Molecular Weight: 655.844
• Mol file: 131372-54-8.mol

Synonyms:5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-fluoro-3'-deoxyadenosine

Chemical Property of 5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-fluoro-3'-deoxyadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-fluoro-3'-deoxyadenosine

There total 6 articles about 5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-fluoro-3'-deoxyadenosine 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: 25.0%

9-<5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-β-D-xylofuranosyl>adenine (83373-09-5) → 5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-fluoro-3'-deoxyadenosine (131372-54-8)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1055/s-1990-27048

Reference yield:

5'-O-(monomethoxytrityl)-2'-O-<(tert-butyl)dimethylsilyl>adenosine (69504-04-7) → 5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-fluoro-3'-deoxyadenosine (131372-54-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / DMAP, Et₃N / CH₂Cl₂ / 1) -40 to -20 deg C, 1 h, 2) rt, 2 h

2: 72 percent / HMPT (hexamethylphosphoric triamide) / 14 h / Ambient temperature

3: 86 percent / Me₂NH / methanol / 1) 0 deg C, 12 - 14 h, 2) rt, 2 h

4: 25 percent / DAST (Et₂NSF₃) / CH₂Cl₂ / 2 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; diethylamino-sulfur trifluoride; dimethyl amine; triethylamine; In methanol; dichloromethane;

DOI:10.1055/s-1990-27048

Reference yield:

9-<5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-O-acetyl-β-D-xylofuranosyl>adenine (131372-49-1) → 5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-fluoro-3'-deoxyadenosine (131372-54-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / Me₂NH / methanol / 1) 0 deg C, 12 - 14 h, 2) rt, 2 h

2: 25 percent / DAST (Et₂NSF₃) / CH₂Cl₂ / 2 h / Ambient temperature

With diethylamino-sulfur trifluoride; dimethyl amine; In methanol; dichloromethane;

DOI:10.1055/s-1990-27048

upstream raw materials:

9-<5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-β-D-xylofuranosyl>adenine

5'-O-(monomethoxytrityl)-2'-O-<(tert-butyl)dimethylsilyl>adenosine

9-<5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-O-acetyl-β-D-xylofuranosyl>adenine

5'-O-(monomethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-3'-O-(trifluoromethanesulfonyl)adenosine

Downstream raw materials:

5'-O-(monomethoxytrityl)-3'-fluoro-3'-deoxyadenosine

(2R,3S,4S,5R)-2-(6-amino-9H-purine-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol