(E)-(2S,5R)-3,5-dimethyl-1,2,6-tris(benzyloxy)-3-hexene

Base Information

Chemical Name:(E)-(2S,5R)-3,5-dimethyl-1,2,6-tris(benzyloxy)-3-hexene
CAS No.:115827-42-4
Molecular Formula:C₂₉H₃₄O₃
Molecular Weight:430.587
Hs Code.:

Synonyms:(E)-(2S,5R)-3,5-dimethyl-1,2,6-tris(benzyloxy)-3-hexene

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Chemical Property of (E)-(2S,5R)-3,5-dimethyl-1,2,6-tris(benzyloxy)-3-hexene

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Technology Process of (E)-(2S,5R)-3,5-dimethyl-1,2,6-tris(benzyloxy)-3-hexene

There total 28 articles about (E)-(2S,5R)-3,5-dimethyl-1,2,6-tris(benzyloxy)-3-hexene 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: 66.0%

: 100-39-0
benzyl bromide

: 115827-35-5
(E)-(2R,5S)-6-(benzyloxy)-2,4-dimethyl-3-hexene-1,5-diol

: 115827-42-4
(E)-(2S,5R)-3,5-dimethyl-1,2,6-tris(benzyloxy)-3-hexene

Guidance literature:: With potassium hydroxide; Tris(3,6-dioxaheptyl)amine; In benzene; for 18h; Ambient temperature;
DOI:10.1021/jo00253a020

Reference yield:

: 115936-20-4,794513-02-3
[(2S,3R)-3-[(benzyloxy)methyl]-2-methyloxiran-2-yl]methanol

: 115827-42-4
(E)-(2S,5R)-3,5-dimethyl-1,2,6-tris(benzyloxy)-3-hexene

Guidance literature:: Multi-step reaction with 5 steps

1: oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 0.75 h / -78 °C

2: 1.) <(CH₃)3Si>2NK (KHMDS) / 1.) THF, toluene, -78 deg C, 5 min, 2.) THF, -78 deg C, 45 min

3: 53 percent / (i-Bu)2AlH (DIBAH) / CH₂Cl₂; hexane / 0.25 h / -78 °C

4: 313 mg / CuI, MeLi / diethyl ether; tetrahydrofuran / 12 h / 0 °C

5: 66 percent / tris-<2-(2-methoxyethoxy)ethyl>amine, KOH / benzene / 18 h / Ambient temperature

With potassium hydroxide; copper(l) iodide; oxalyl dichloride; Tris(3,6-dioxaheptyl)amine; methyllithium; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/jo00253a020

Reference yield:

: 115827-26-4
(2Z)-4-(benzyloxy)-2-methylbut-2-en-1-ol

: 115827-42-4
(E)-(2S,5R)-3,5-dimethyl-1,2,6-tris(benzyloxy)-3-hexene

Guidance literature:: Multi-step reaction with 6 steps

1: 3-Angstroem molecular sieves, L-(+)-diethyl tartrate, titanium(IV)isopropoxide, tert-butyl hydroperoxide / 2,2,4-trimethyl-pentane; CH₂Cl₂ / 14 h / -20 °C

2: oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 0.75 h / -78 °C

3: 1.) <(CH₃)3Si>2NK (KHMDS) / 1.) THF, toluene, -78 deg C, 5 min, 2.) THF, -78 deg C, 45 min

4: 53 percent / (i-Bu)2AlH (DIBAH) / CH₂Cl₂; hexane / 0.25 h / -78 °C

5: 313 mg / CuI, MeLi / diethyl ether; tetrahydrofuran / 12 h / 0 °C

6: 66 percent / tris-<2-(2-methoxyethoxy)ethyl>amine, KOH / benzene / 18 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium hydroxide; copper(l) iodide; oxalyl dichloride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; Tris(3,6-dioxaheptyl)amine; methyllithium; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/jo00253a020