(4S,5R)-1-acetoxy-5-(2-acetoxyethyl)-4-isopropenyl-5-methyl-1-cyclohexene

Base Information

Chemical Name:(4S,5R)-1-acetoxy-5-(2-acetoxyethyl)-4-isopropenyl-5-methyl-1-cyclohexene
CAS No.:144264-22-2
Molecular Formula:C₁₆H₂₄O₄
Molecular Weight:280.364
Hs Code.:

Synonyms:(4S,5R)-1-acetoxy-5-(2-acetoxyethyl)-4-isopropenyl-5-methyl-1-cyclohexene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4S,5R)-1-acetoxy-5-(2-acetoxyethyl)-4-isopropenyl-5-methyl-1-cyclohexene

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Technology Process of (4S,5R)-1-acetoxy-5-(2-acetoxyethyl)-4-isopropenyl-5-methyl-1-cyclohexene

There total 5 articles about (4S,5R)-1-acetoxy-5-(2-acetoxyethyl)-4-isopropenyl-5-methyl-1-cyclohexene 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: 79.0%

: 108-24-7
acetic anhydride

: 144264-21-1
(1R,4R,5R)-4-(2-acetoxyethyl)-4,6,6-trimethylbicyclo<3.1.1>heptan-2-one

: 144264-22-2
(4S,5R)-1-acetoxy-5-(2-acetoxyethyl)-4-isopropenyl-5-methyl-1-cyclohexene

Guidance literature:: With boron trifluoride diethyl etherate; zinc diacetate; for 96h; Ambient temperature;
DOI:10.1246/bcsj.65.2071

Reference yield:

: 128261-62-1
(1R,4S,5R)-(+)-4,6,6-trimethyl-4-vinylbicyclo<3.1.1>heptan-2-one

: 144264-22-2
(4S,5R)-1-acetoxy-5-(2-acetoxyethyl)-4-isopropenyl-5-methyl-1-cyclohexene

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / p-toluenesulfonic acid / benzene / 13 h

2: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) aq. NaOH, 30percent H₂O₂ / 1.) THF, a) 0 deg C, 30 min, b) RT, 17 h, 2.) THF, a) 0 deg C, 30 min, b) RT, 6 h

3: 96 percent / pyridine / 10 h / Ambient temperature

4: 93 percent / p-toluenesulfonic acid / acetone / 4 h / Ambient temperature

5: 79 percent / BF₃*Et₂O, (CH₃COO)2Zn / 96 h / Ambient temperature

With pyridine; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; boron trifluoride diethyl etherate; zinc diacetate; dihydrogen peroxide; toluene-4-sulfonic acid; In acetone; benzene;
DOI:10.1246/bcsj.65.2071

Reference yield:

: 144264-18-6
(1R,4S,5R)-4,6,6-trimethyl-4-vinylbicyclo<3.1.1>heptan-2-one ethylene acetal

: 144264-22-2
(4S,5R)-1-acetoxy-5-(2-acetoxyethyl)-4-isopropenyl-5-methyl-1-cyclohexene

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) aq. NaOH, 30percent H₂O₂ / 1.) THF, a) 0 deg C, 30 min, b) RT, 17 h, 2.) THF, a) 0 deg C, 30 min, b) RT, 6 h

2: 96 percent / pyridine / 10 h / Ambient temperature

3: 93 percent / p-toluenesulfonic acid / acetone / 4 h / Ambient temperature

4: 79 percent / BF₃*Et₂O, (CH₃COO)2Zn / 96 h / Ambient temperature

With pyridine; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; boron trifluoride diethyl etherate; zinc diacetate; dihydrogen peroxide; toluene-4-sulfonic acid; In acetone;
DOI:10.1246/bcsj.65.2071