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

Base Information

Chemical Name:(1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-3′-O-(diisopropylphosphonomethyl)-L-threose
CAS No.:1446785-65-4
Molecular Formula:C₃₂H₃₄N₅O₈P
Molecular Weight:647.624
Hs Code.:

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

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

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

There total 8 articles about (1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-3′-O-(diisopropylphosphonomethyl)-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: 88.0%

: 134963-85-2
(diisopropoxyphosphoryl)methyl trifluoromethanesulfonate

: 1446785-62-1
(1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-L-threose

: 1446785-65-4
(1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-3′-O-(diisopropylphosphonomethyl)-L-threose

Guidance literature:: With sodium hydride; In tetrahydrofuran; mineral oil; at -15 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jo400907g

Reference yield:

: 1-O-acetyl-2-O-benzoyl-3-O-tert-butyldiphenylsilyl-L-threofuranose

: 1446785-65-4
(1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-3′-O-(diisopropylphosphonomethyl)-L-threose

Guidance literature:: Multi-step reaction with 5 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

5.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / -15 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; cerium(III) chloride; tetrabutyl ammonium fluoride; water; sodium hydride; Dess-Martin periodane; acetic acid; In tetrahydrofuran; dichloromethane; acetonitrile; mineral oil;
DOI:10.1021/jo400907g

Reference yield:

: 1446785-56-3
N⁶-benzoyl-9-(2′-O-benzoyl-α-L-threofuranosyl)adenine

: 1446785-65-4
(1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-3′-O-(diisopropylphosphonomethyl)-L-threose

Guidance literature:: Multi-step reaction with 3 steps

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

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

2.2: 4.17 h / -78 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / -15 °C / Inert atmosphere

With cerium(III) chloride; water; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; mineral oil;
DOI:10.1021/jo400907g