(4S)-(Z)-1-methylene-2-(1'-acetoxyethenyl-2')-4-hydroxycyclohexane

Base Information

Chemical Name:(4S)-(Z)-1-methylene-2-(1'-acetoxyethenyl-2')-4-hydroxycyclohexane
CAS No.:144066-62-6
Molecular Formula:C₁₁H₁₆O₃
Molecular Weight:196.246
Hs Code.:

Synonyms:(4S)-(Z)-1-methylene-2-(1'-acetoxyethenyl-2')-4-hydroxycyclohexane

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Chemical Property of (4S)-(Z)-1-methylene-2-(1'-acetoxyethenyl-2')-4-hydroxycyclohexane

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Technology Process of (4S)-(Z)-1-methylene-2-(1'-acetoxyethenyl-2')-4-hydroxycyclohexane

There total 11 articles about (4S)-(Z)-1-methylene-2-(1'-acetoxyethenyl-2')-4-hydroxycyclohexane 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: 90.0%

: 144066-61-5,144066-76-2
(4S)-(Z)-1-methylene-2-(1'-acetoxyethenyl-2')-4-hydroxycyclohexan (2RS)-4-tetrahydropyranyl ether

: 144066-62-6
(4S)-(Z)-1-methylene-2-(1'-acetoxyethenyl-2')-4-hydroxycyclohexane

Guidance literature:: With methanol; pyridinium p-toluenesulfonate; Ambient temperature;

Reference yield:

: 144066-52-4
(6S,8aS)-6-Hydroxy-8a-methyl-3,4,6,7,8,8a-hexahydro-chromen-2-one

: 144066-62-6
(4S)-(Z)-1-methylene-2-(1'-acetoxyethenyl-2')-4-hydroxycyclohexane

Guidance literature:: Multi-step reaction with 10 steps

1: pyridinium p-toluenesulfonate (PPTS) / CH₂Cl₂ / Ambient temperature

2: 1.) lithium diisopropylamide (LDA), 2.) MoOPH, hexamethylphosphoric triamide (HMPA) / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, from -78 deg C to up to 0 deg C

3: 4.3 g / LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

4: 90 percent / aq. NaIO₄ / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 87 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / Ambient temperature

6: 93 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 0.25 h / Ambient temperature

7: 800 mg / diisobutylaluminum hydride (DIBAH) / toluene / 3 h / Ambient temperature

8: 90 percent / pyridine / Ambient temperature

9: 89 percent / 6H₅C(CF₃)2O>2S(C₆H₅)2 (Martin reagent) / 5 h / Ambient temperature

10: 90 percent / pyridinium p-toluenesulfonate (PPTS), methanol / Ambient temperature

With pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; lithium aluminium tetrahydride; Martins sulfurane; MoO₅*pyridine*HMPA; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;

Reference yield:

: 144125-10-0
(S)-8a-Methyl-3,4,8,8a-tetrahydro-7H-chromene-2,6-dione

: 144066-62-6
(4S)-(Z)-1-methylene-2-(1'-acetoxyethenyl-2')-4-hydroxycyclohexane

Guidance literature:: Multi-step reaction with 11 steps

1: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 2 h / Ambient temperature

2: pyridinium p-toluenesulfonate (PPTS) / CH₂Cl₂ / Ambient temperature

3: 1.) lithium diisopropylamide (LDA), 2.) MoOPH, hexamethylphosphoric triamide (HMPA) / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, from -78 deg C to up to 0 deg C

4: 4.3 g / LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

5: 90 percent / aq. NaIO₄ / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 87 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / Ambient temperature

7: 93 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 0.25 h / Ambient temperature

8: 800 mg / diisobutylaluminum hydride (DIBAH) / toluene / 3 h / Ambient temperature

9: 90 percent / pyridine / Ambient temperature

10: 89 percent / 6H₅C(CF₃)2O>2S(C₆H₅)2 (Martin reagent) / 5 h / Ambient temperature

11: 90 percent / pyridinium p-toluenesulfonate (PPTS), methanol / Ambient temperature

With pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; lithium aluminium tetrahydride; Martins sulfurane; MoO₅*pyridine*HMPA; lithium tri(t-butoxy)aluminum hydride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;