(S)-23-benzyloxy-5-methyltricos-8-yn-1-ol tetrahydropyranyl ether

Base Information

Chemical Name:(S)-23-benzyloxy-5-methyltricos-8-yn-1-ol tetrahydropyranyl ether
CAS No.:79015-91-1
Molecular Formula:C₃₆H₆₀O₃
Molecular Weight:540.871
Hs Code.:

Synonyms:

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Chemical Property of (S)-23-benzyloxy-5-methyltricos-8-yn-1-ol tetrahydropyranyl ether

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Technology Process of (S)-23-benzyloxy-5-methyltricos-8-yn-1-ol tetrahydropyranyl ether

There total 21 articles about (S)-23-benzyloxy-5-methyltricos-8-yn-1-ol tetrahydropyranyl ether 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:

: 1117-61-9
(3R)-citronellol

: 79015-91-1
(S)-23-benzyloxy-5-methyltricos-8-yn-1-ol tetrahydropyranyl ether

Guidance literature:: Multi-step reaction with 13 steps

1: pyridine / 2 h / 0 - 5 °C

2: 85 percent / sodium iodide / acetone / 1.) reflux, 4 h; 2.) room temp., 14 h

3: 78 percent / NaOEt / ethanol / 1.) 0-5 deg C, 1 h; 2.) reflux, 4 h

4: 92 percent / KOH / aq. ethanol / 2.5 h / Heating

5: 92 percent / LAH / diethyl ether / 4 h / Ambient temperature

6: 96.5 percent / pyridine / 5 h / Ambient temperature

7: 90 percent / m-chloroperbenzoic acid / CHCl₃

8: 81 percent / HIO₄*2H₂O / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature

9: 1.) n-buLi / 1.) n-hexane, THF, -30 deg C; 2.) -50 to -10 deg C, THF, -10 deg C, 1 h

10: 85 percent / Br₂ / CH₂Cl₂ / 1 h

11: 69.4 percent / NaNH₂, 10 percent NaOH / methanol / 0.5 h / Heating

12: 5.85 g / p-TsOH / diethyl ether / Ambient temperature

13: 13.2 g / n-BuLI / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 1 h / Ambient temperature

With potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; bromine; sodium ethanolate; sodium amide; periodic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane; chloroform; acetone;
DOI:10.1016/S0040-4020(01)92448-2

Reference yield:

: 18951-85-4,57030-77-0
(R)-citronellic acid

: 79015-91-1
(S)-23-benzyloxy-5-methyltricos-8-yn-1-ol tetrahydropyranyl ether

Guidance literature:: Multi-step reaction with 14 steps

1: 92 percent / LAH / diethyl ether / 3 h / Ambient temperature

2: pyridine / 2 h / 0 - 5 °C

3: 85 percent / sodium iodide / acetone / 1.) reflux, 4 h; 2.) room temp., 14 h

4: 78 percent / NaOEt / ethanol / 1.) 0-5 deg C, 1 h; 2.) reflux, 4 h

5: 92 percent / KOH / aq. ethanol / 2.5 h / Heating

6: 92 percent / LAH / diethyl ether / 4 h / Ambient temperature

7: 96.5 percent / pyridine / 5 h / Ambient temperature

8: 90 percent / m-chloroperbenzoic acid / CHCl₃

9: 81 percent / HIO₄*2H₂O / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature

10: 1.) n-buLi / 1.) n-hexane, THF, -30 deg C; 2.) -50 to -10 deg C, THF, -10 deg C, 1 h

11: 85 percent / Br₂ / CH₂Cl₂ / 1 h

12: 69.4 percent / NaNH₂, 10 percent NaOH / methanol / 0.5 h / Heating

13: 5.85 g / p-TsOH / diethyl ether / Ambient temperature

14: 13.2 g / n-BuLI / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 1 h / Ambient temperature

With potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; bromine; sodium ethanolate; sodium amide; periodic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane; chloroform; acetone;
DOI:10.1016/S0040-4020(01)92448-2

Reference yield:

: 69274-74-4
(S)-(+)-8-acetoxy-4-methyloctanal

: 79015-91-1
(S)-23-benzyloxy-5-methyltricos-8-yn-1-ol tetrahydropyranyl ether

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) n-buLi / 1.) n-hexane, THF, -30 deg C; 2.) -50 to -10 deg C, THF, -10 deg C, 1 h

2: 85 percent / Br₂ / CH₂Cl₂ / 1 h

3: 69.4 percent / NaNH₂, 10 percent NaOH / methanol / 0.5 h / Heating

4: 5.85 g / p-TsOH / diethyl ether / Ambient temperature

5: 13.2 g / n-BuLI / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 1 h / Ambient temperature

With sodium hydroxide; n-butyllithium; bromine; sodium amide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane;
DOI:10.1016/S0040-4020(01)92448-2