[3S-(1Z,3β,5α)]-2-[5-(3-methyl-2-butenoxy)-3-tetrahydropyranyloxy-2-methylenecyclohexylidene]-1-chloroethane

Base Information

Chemical Name:[3S-(1Z,3β,5α)]-2-[5-(3-methyl-2-butenoxy)-3-tetrahydropyranyloxy-2-methylenecyclohexylidene]-1-chloroethane
CAS No.:342645-74-3
Molecular Formula:C₁₉H₂₉ClO₃
Molecular Weight:340.89
Hs Code.:

Synonyms:[3S-(1Z,3β,5α)]-2-[5-(3-methyl-2-butenoxy)-3-tetrahydropyranyloxy-2-methylenecyclohexylidene]-1-chloroethane

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Chemical Property of [3S-(1Z,3β,5α)]-2-[5-(3-methyl-2-butenoxy)-3-tetrahydropyranyloxy-2-methylenecyclohexylidene]-1-chloroethane

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Technology Process of [3S-(1Z,3β,5α)]-2-[5-(3-methyl-2-butenoxy)-3-tetrahydropyranyloxy-2-methylenecyclohexylidene]-1-chloroethane

There total 15 articles about [3S-(1Z,3β,5α)]-2-[5-(3-methyl-2-butenoxy)-3-tetrahydropyranyloxy-2-methylenecyclohexylidene]-1-chloroethane 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: 87.0%

: 342645-73-2
[3S,(1Z,3β,5α)]-2-[5-(3-methyl-2-butenoxy)-3-tetrahydropyranyloxy-2-methylenecyclohexylidene]ethanol

: 342645-74-3
[3S-(1Z,3β,5α)]-2-[5-(3-methyl-2-butenoxy)-3-tetrahydropyranyloxy-2-methylenecyclohexylidene]-1-chloroethane

Guidance literature:: [3S,(1Z,3β,5α)]-2-[5-(3-methyl-2-butenoxy)-3-tetrahydropyranyloxy-2-methylenecyclohexylidene]ethanol; With 2,6-dimethylpyridine; lithium chloride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

With methanesulfonyl chloride; In N,N-dimethyl-formamide; at 0 ℃; for 0.666667h; Further stages.;
DOI:10.1021/ja003976k

Reference yield:

: 342644-76-2
(3S,5S)-5,6-epoxy-3-tetrahydropyranyloxy-1-hexene

: 342645-74-3
[3S-(1Z,3β,5α)]-2-[5-(3-methyl-2-butenoxy)-3-tetrahydropyranyloxy-2-methylenecyclohexylidene]-1-chloroethane

Guidance literature:: Multi-step reaction with 13 steps

1.1: MgSO₄ / methanol; H₂O / 12 h / 20 °C

2.1: imidazole / dimethylformamide / 10 h / 20 °C

3.1: DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

4.1: 12.30 g / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 0 °C

5.1: carbonyl diimidazole / tetrahydrofuran / 3 h / 20 °C

5.2: tetrahydrofuran / 24 h / 20 °C

6.1: NaH / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C

6.2: tetrahydrofuran; various solvent(s) / 12 h / 20 °C

7.1: 13.14 g / DIBAL / toluene; tetrahydrofuran / 2 h / -78 °C

8.1: 57 percent / Pd(OAc)2; PPh₃; Et₃N / dimethylformamide / 6 h / 30 °C

9.1: 91 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 0 °C

10.1: 99 percent / TBAF*xH₂O / tetrahydrofuran / 1 h / 20 °C

11.1: 77 percent / NaH; tetrabutylammonium iodide / dimethylformamide; various solvent(s) / 20 h / 20 °C

12.1: 86 percent / DIBAL / CH₂Cl₂; toluene / 0.67 h / -78 °C

13.1: 2,6-lutidine; LiCl / dimethylformamide / 0.5 h / 0 °C

13.2: 87 percent / methanesulfonyl chloride / dimethylformamide / 0.67 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; palladium diacetate; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; magnesium sulfate; triethylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 8.1: Mizoroki-Heck reaction;
DOI:10.1021/ja003976k

Reference yield:

: 342645-63-0
(3R,5S)-3-hydroxy-5-tetrahydropyranyloxy-6-heptenitrile

: 342645-74-3
[3S-(1Z,3β,5α)]-2-[5-(3-methyl-2-butenoxy)-3-tetrahydropyranyloxy-2-methylenecyclohexylidene]-1-chloroethane

Guidance literature:: Multi-step reaction with 12 steps

1.1: imidazole / dimethylformamide / 10 h / 20 °C

2.1: DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

3.1: 12.30 g / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 0 °C

4.1: carbonyl diimidazole / tetrahydrofuran / 3 h / 20 °C

4.2: tetrahydrofuran / 24 h / 20 °C

5.1: NaH / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C

5.2: tetrahydrofuran; various solvent(s) / 12 h / 20 °C

6.1: 13.14 g / DIBAL / toluene; tetrahydrofuran / 2 h / -78 °C

7.1: 57 percent / Pd(OAc)2; PPh₃; Et₃N / dimethylformamide / 6 h / 30 °C

8.1: 91 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 0 °C

9.1: 99 percent / TBAF*xH₂O / tetrahydrofuran / 1 h / 20 °C

10.1: 77 percent / NaH; tetrabutylammonium iodide / dimethylformamide; various solvent(s) / 20 h / 20 °C

11.1: 86 percent / DIBAL / CH₂Cl₂; toluene / 0.67 h / -78 °C

12.1: 2,6-lutidine; LiCl / dimethylformamide / 0.5 h / 0 °C

12.2: 87 percent / methanesulfonyl chloride / dimethylformamide / 0.67 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; palladium diacetate; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; lithium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 7.1: Mizoroki-Heck reaction;
DOI:10.1021/ja003976k