2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

Base Information

• Chemical Name: 2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate
• CAS No.: 622405-00-9
• Molecular Formula: C₂₅H₃₈O₅
• Molecular Weight: 418.574
• Mol file: 622405-00-9.mol

Synonyms:2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

Chemical Property of 2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

There total 10 articles about 2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate 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%

2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-{[(tert-butyl)dimethylsilyl]oxy}pentanoate (622404-99-3) → 2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate (622405-00-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1002/hlca.200390151

Reference yield:

2-allyl-cyclohex-2-enone (38019-50-0) → 2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate (622405-00-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: CuI / diethyl ether; hexane / 1 h / -78 °C

1.2: 80 percent / methyl 2-hydroxybenzoate / diethyl ether; hexane / -78 - 20 °C

2.1: 87 percent / trimethylsilyl triflate / CH₂Cl₂ / 12 h / -78 - 20 °C

3.1: 90 percent / hexane; CH₂Cl₂ / 12 h / -78 - 0 °C

4.1: 79 percent / DMAP; Et₃N; 2,4,6-trichlorobenzoyl chloride / toluene / 20 h / 0 °C

5.1: 66 percent / Bu₄NF / tetrahydrofuran / 0 - 20 °C

With dmap; copper(l) iodide; trimethylsilyl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 4.1: Yamaguchi activation;

DOI:10.1002/hlca.200390151

Reference yield:

trans-3-Methyl-2-(2-propenyl)cyclohexanone (61674-94-0,795275-74-0) → 2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate (622405-00-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / trimethylsilyl triflate / CH₂Cl₂ / 12 h / -78 - 20 °C

2: 90 percent / hexane; CH₂Cl₂ / 12 h / -78 - 0 °C

3: 79 percent / DMAP; Et₃N; 2,4,6-trichlorobenzoyl chloride / toluene / 20 h / 0 °C

4: 66 percent / Bu₄NF / tetrahydrofuran / 0 - 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; 3: Yamaguchi activation;

DOI:10.1002/hlca.200390151

upstream raw materials:

2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-{[(tert-butyl)dimethylsilyl]oxy}pentanoate

2-allyl-cyclohex-2-enone

trans-3-Methyl-2-(2-propenyl)cyclohexanone

(R)-2-benzyloxypropanal

Downstream raw materials:

(7R,10E,12aS,13S,16aR)-7-[(1R)-1-(benzyloxy)ethyl]-2,3,6,7,12a,13,14,15,16,16a-decahydro-13,16a-dimethyl-5H-1,4,8-benzotrioxacyclotetradecine-5,9(12H)-dione

(7R,10E,12aR,13R,16aS)-7-[(1R)-1-(benzyloxy)ethyl]-2,3,6,7,12a,13,14,15,16,16a-decahydro-13,16a-dimethyl-5H-1,4,8-benzotrioxacyclotetradecine-5,9(12H)-dione