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
Hs Code.:

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

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

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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%

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

: 622405-00-9
2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1002/hlca.200390151

Reference yield:

: 38019-50-0
2-allyl-cyclohex-2-enone

: 622405-00-9
2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

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:

: 61674-94-0,795275-74-0
trans-3-Methyl-2-(2-propenyl)cyclohexanone

: 622405-00-9
2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

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