N⁶-benzoyl-9-(2′-O-benzoyl-3′-O-tert-butyldiphenylsilyl-α-L-threofuranosyl)adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-(2′-O-benzoyl-3′-O-tert-butyldiphenylsilyl-α-L-threofuranosyl)adenine
• CAS No.: 1446785-49-4
• Molecular Formula: C₃₉H₃₇N₅O₅Si
• Molecular Weight: 683.839
• Mol file: 1446785-49-4.mol

Synonyms:N⁶-benzoyl-9-(2′-O-benzoyl-3′-O-tert-butyldiphenylsilyl-α-L-threofuranosyl)adenine

Chemical Property of N⁶-benzoyl-9-(2′-O-benzoyl-3′-O-tert-butyldiphenylsilyl-α-L-threofuranosyl)adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-benzoyl-9-(2′-O-benzoyl-3′-O-tert-butyldiphenylsilyl-α-L-threofuranosyl)adenine

There total 7 articles about N⁶-benzoyl-9-(2′-O-benzoyl-3′-O-tert-butyldiphenylsilyl-α-L-threofuranosyl)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: 51.0%

1-O-acetyl-2-O-benzoyl-3-O-tert-butyldiphenylsilyl-L-threofuranose + N-benzoyladenine (4005-49-6) → N6-benzoyl-9-(2′-O-benzoyl-3′-O-tert-butyldiphenylsilyl-α-L-threofuranosyl)adenine (1446785-49-4) + C39H37N5O5Si (1446785-51-8)

Guidance literature:

N-benzoyladenine; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 20 ℃; for 0.333333h;

1-O-acetyl-2-O-benzoyl-3-O-tert-butyldiphenylsilyl-L-threofuranose; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 70 ℃;

DOI:10.1021/jo400907g

Reference yield: 45.0%

C39H37N5O5Si (1446785-51-8) → N6-benzoyl-9-(2′-O-benzoyl-3′-O-tert-butyldiphenylsilyl-α-L-threofuranosyl)adenine (1446785-49-4)

Guidance literature:

With toluene-4-sulfonic acid; In water; toluene; at 130 ℃;

DOI:10.1021/jo400907g

Reference yield:

2-O-Benzoyl-3-O-tert-butyldiphenylsilyl-L-threonolactone (1446785-28-9) → N6-benzoyl-9-(2′-O-benzoyl-3′-O-tert-butyldiphenylsilyl-α-L-threofuranosyl)adenine (1446785-49-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / 1,2-dimethoxyethane; toluene / 0.5 h / -78 °C / Inert atmosphere

2.1: dmap / dichloromethane / 1.67 h / -78 - 20 °C / Inert atmosphere

3.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 0.5 h / 95 °C / Inert atmosphere

3.2: 2.5 h / 95 °C / Inert atmosphere

With dmap; N,O-bis-(trimethylsilyl)-acetamide; diisobutylaluminium hydride; In 1,2-dimethoxyethane; dichloromethane; toluene; 3.1: |Vorbrueggen Nucleoside Synthesis / 3.2: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1021/acs.joc.5b02768

upstream raw materials:

C₃₉H₃₇N₅O₅Si

N-benzoyladenine

2′-O-benzoyl-L-threonolactone

2-O-Benzoyl-3-O-tert-butyldiphenylsilyl-L-threonolactone

Downstream raw materials:

N⁶-benzoyl-9-(2′-O-benzoyl-α-L-threofuranosyl)adenine

1′α-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-oxo-L-threose

(1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-L-threose

(1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-3′-O-(diisopropylphosphonomethyl)-L-threose