(2S,4S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-octane-2,4-diol

Base Information

Chemical Name:(2S,4S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-octane-2,4-diol
CAS No.:868566-21-6
Molecular Formula:C₁₉H₃₀O₄
Molecular Weight:322.445
Hs Code.:

Synonyms:(2S,4S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-octane-2,4-diol

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Chemical Property of (2S,4S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-octane-2,4-diol

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Technology Process of (2S,4S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-octane-2,4-diol

There total 10 articles about (2S,4S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-octane-2,4-diol 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: 95.0%

: 868566-35-2
Benzoic acid (1S,3S)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-hydroxy-7-phenyl-heptyl ester

: 868566-21-6
(2S,4S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-octane-2,4-diol

Guidance literature:: With sodium; In methanol; at 20 ℃; for 2h;
DOI:10.1021/jo050972v

Reference yield:

: 868566-22-7
2-O-benzyl-3,5-dideoxy-6,7-O-isopropylidene-D-xyloheptoic-γ-lactone

: 868566-21-6
(2S,4S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-octane-2,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 97 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 20 °C

2.2: 96 percent / tetrahydrofuran; hexane / 12 h / 20 °C

3.1: 69 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 0 °C

4.1: 96 percent / H₂ / Raney nickel / ethanol / 12 h / 1034.3 Torr

5.1: 95 percent / Na / methanol / 2 h / 20 °C

With n-butyllithium; hydrogen; sodium; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene; 2.2: Wittig olefination reaction / 3.1: Mitsunobu reaction;
DOI:10.1021/jo050972v

Reference yield:

: (3R,5S)-3-Benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-furan-2-ol

: 868566-21-6
(2S,4S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-octane-2,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 20 °C

1.2: 96 percent / tetrahydrofuran; hexane / 12 h / 20 °C

2.1: 69 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 0 °C

3.1: 96 percent / H₂ / Raney nickel / ethanol / 12 h / 1034.3 Torr

4.1: 95 percent / Na / methanol / 2 h / 20 °C

With n-butyllithium; hydrogen; sodium; triphenylphosphine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; ethanol; hexane; 1.2: Wittig olefination reaction / 2.1: Mitsunobu reaction;
DOI:10.1021/jo050972v