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

Base Information

• Chemical Name: (1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-L-threose
• CAS No.: 1446785-62-1
• Molecular Formula: C₂₅H₁₉N₅O₅
• Molecular Weight: 469.456
• Mol file: 1446785-62-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-L-threose 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: 32.0%

1′α-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-oxo-L-threose (1446785-59-6) + acetylenemagnesium bromide (4301-14-8) → (1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-L-threose (1446785-62-1)

Guidance literature:

acetylenemagnesium bromide; With cerium(III) chloride; In tetrahydrofuran; at -78 ℃; for 1.83333h; Inert atmosphere;

1′α-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-oxo-L-threose; In tetrahydrofuran; at -78 ℃; for 4.16667h; Inert atmosphere;

DOI:10.1021/jo400907g

Reference yield:

1-O-acetyl-2-O-benzoyl-3-O-tert-butyldiphenylsilyl-L-threofuranose → (1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-L-threose (1446785-62-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.33 h / 20 °C

1.2: 0 - 70 °C

2.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 20 °C

3.1: Dess-Martin periodane; water / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: cerium(III) chloride / tetrahydrofuran / 1.83 h / -78 °C / Inert atmosphere

4.2: 4.17 h / -78 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; cerium(III) chloride; tetrabutyl ammonium fluoride; water; Dess-Martin periodane; acetic acid; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jo400907g

Reference yield:

N-benzoyladenine (4005-49-6) → (1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-L-threose (1446785-62-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.33 h / 20 °C

1.2: 0 - 70 °C

2.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 20 °C

3.1: Dess-Martin periodane; water / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: cerium(III) chloride / tetrahydrofuran / 1.83 h / -78 °C / Inert atmosphere

4.2: 4.17 h / -78 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; cerium(III) chloride; tetrabutyl ammonium fluoride; water; Dess-Martin periodane; acetic acid; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jo400907g

upstream raw materials:

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

C₃₉H₃₇N₅O₅Si

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

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

Downstream raw materials:

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