(R)-5-[(E)-3-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-but-2-enyl]-2,2,4,4-tetramethyl-[1,3]dioxolane

Base Information

Chemical Name:(R)-5-[(E)-3-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-but-2-enyl]-2,2,4,4-tetramethyl-[1,3]dioxolane
CAS No.:141211-01-0
Molecular Formula:C₂₃H₃₈O₂
Molecular Weight:346.554
Hs Code.:

Synonyms:(R)-5-[(E)-3-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-but-2-enyl]-2,2,4,4-tetramethyl-[1,3]dioxolane

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Chemical Property of (R)-5-[(E)-3-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-but-2-enyl]-2,2,4,4-tetramethyl-[1,3]dioxolane

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Technology Process of (R)-5-[(E)-3-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-but-2-enyl]-2,2,4,4-tetramethyl-[1,3]dioxolane

There total 12 articles about (R)-5-[(E)-3-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-but-2-enyl]-2,2,4,4-tetramethyl-[1,3]dioxolane 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: 84.0%

: 1-{(1S,2R,5S)-2-Methyl-5-[(E)-1-methyl-3-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-propenyl]-2-vinyl-cyclohexyl}-ethanone

: 74-95-3
1,1-dibromomethane

: 141211-01-0
(R)-5-[(E)-3-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-but-2-enyl]-2,2,4,4-tetramethyl-[1,3]dioxolane

Guidance literature:: With titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane; at 23 ℃; for 1h;
DOI:10.1248/cpb.40.556

Reference yield:

: 139694-37-4
(1S,2R,5S)-5-Acetyl-2-methyl-2-vinyl-cyclohexanecarboxylic acid methyl ester

: 141211-01-0
(R)-5-[(E)-3-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-but-2-enyl]-2,2,4,4-tetramethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) BuLi, 2.) BF₃*OEt₂ / 2.) THF, -78 deg C , 20 min

2: SOCl₂, pyridine / 0.08 h / 0 °C

3: 76 percent / Li, NH₃ (liquid) / ethanol / 0.33 h / -78 °C

4: 88 percent / PDC, 4A MS / CH₂Cl₂ / 24 °C

5: 98 percent / diethyl ether / 0.08 h / -70 °C

6: 95 percent / PDC, 4A MS / CH₂Cl₂ / 0.5 h / 24 °C

7: 84 percent / Zn, TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 1 h / 23 °C

With pyridine; dipyridinium dichromate; n-butyllithium; thionyl chloride; boron trifluoride diethyl etherate; ammonia; titanium tetrachloride; lithium; zinc; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;
DOI:10.1248/cpb.40.556

Reference yield:

: 141210-95-9
(1S,2R,5R,6R)-5-Acetyl-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-2-vinyl-cyclohexanecarboxylic acid methyl ester

: 141211-01-0
(R)-5-[(E)-3-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-but-2-enyl]-2,2,4,4-tetramethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 9 steps

1: 83 percent / MeONa

2: 1.) 80percent AcOH, 2.) NaIO₄, 3.) NaClO₂, 4.) (COCl)2, pyridine, 5.) N-hydroxypyridine-2-thione sodium salt, DMAP, 6.) Bu₃SnH, AIBN

3: 1.) BuLi, 2.) BF₃*OEt₂ / 2.) THF, -78 deg C , 20 min

4: SOCl₂, pyridine / 0.08 h / 0 °C

5: 76 percent / Li, NH₃ (liquid) / ethanol / 0.33 h / -78 °C

6: 88 percent / PDC, 4A MS / CH₂Cl₂ / 24 °C

7: 98 percent / diethyl ether / 0.08 h / -70 °C

8: 95 percent / PDC, 4A MS / CH₂Cl₂ / 0.5 h / 24 °C

9: 84 percent / Zn, TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 1 h / 23 °C

With pyridine; dmap; sodium chlorite; sodium periodate; dipyridinium dichromate; n-butyllithium; thionyl chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; ammonia; tri-n-butyl-tin hydride; sodium methylate; 2-mercaptopyridine-1-oxide sodium salt; titanium tetrachloride; lithium; acetic acid; zinc; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;
DOI:10.1248/cpb.40.556