(Z)-(2R,4R)-4-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-oct-5-en-2-ol

Base Information

Chemical Name:(Z)-(2R,4R)-4-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-oct-5-en-2-ol
CAS No.:868566-26-1
Molecular Formula:C₂₆H₃₄O₄
Molecular Weight:410.554
Hs Code.:

Synonyms:(Z)-(2R,4R)-4-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-oct-5-en-2-ol

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Chemical Property of (Z)-(2R,4R)-4-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-oct-5-en-2-ol

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Technology Process of (Z)-(2R,4R)-4-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-oct-5-en-2-ol

There total 8 articles about (Z)-(2R,4R)-4-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-oct-5-en-2-ol 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: 96.0%

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

: (3-phenylpropyl)triphenylphosphonium iodide

: 868566-26-1
(Z)-(2R,4R)-4-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-oct-5-en-2-ol

Guidance literature:: (3-phenylpropyl)triphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 1h;

(3R,5S)-3-Benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-furan-2-ol; In tetrahydrofuran; hexane; at 20 ℃; for 12h;
DOI:10.1021/jo050972v

Reference yield:

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

: 868566-26-1
(Z)-(2R,4R)-4-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-oct-5-en-2-ol

Guidance literature:: Multi-step reaction with 2 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

With n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; toluene; 2.2: Wittig olefination reaction;
DOI:10.1021/jo050972v

Reference yield:

: 868566-23-8
2-benzyloxy-3-deoxy-6,7-O-isopropylidene-D-arabinohept-2-enoic-γ-lactone

: 868566-26-1
(Z)-(2R,4R)-4-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-oct-5-en-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 61 percent / NaBH₄; NiCl₂*6H₂O; AcOH / methanol / 1 h / 0 °C / pH 7

2.1: NaH / tetrahydrofuran / 0.5 h / -15 °C

2.2: 93 percent / tetrahydrofuran / 12 h / 20 °C

3.1: 71 percent / Bu₃SnH; AIBN / toluene / 5 h / Heating

4.1: 97 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

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

5.2: 96 percent / tetrahydrofuran; hexane / 12 h / 20 °C

With sodium tetrahydroborate; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; acetic acid; nickel dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 5.2: Wittig olefination reaction;
DOI:10.1021/jo050972v