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

Base Information

• Chemical Name: 2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-{[(tert-butyl)dimethylsilyl]oxy}pentanoate
• CAS No.: 622404-99-3
• Molecular Formula: C₃₁H₅₂O₅Si
• Molecular Weight: 532.836
• Mol file: 622404-99-3.mol

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

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

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-{[(tert-butyl)dimethylsilyl]oxy}pentanoate

There total 8 articles about 2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-{[(tert-butyl)dimethylsilyl]oxy}pentanoate 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%

2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethanol + (3R,4R)-4-(benzyloxy)-3-{[(tert-butyl)dimethylsilyl]oxy}pentanoic acid (620615-98-7) → 2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-{[(tert-butyl)dimethylsilyl]oxy}pentanoate (622404-99-3)

Guidance literature:

With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In toluene; at 0 ℃; for 20h;

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-{[(tert-butyl)dimethylsilyl]oxy}pentanoate (622404-99-3)

Guidance literature:

Multi-step reaction with 4 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

With dmap; copper(l) iodide; trimethylsilyl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; triethylamine; In 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-{[(tert-butyl)dimethylsilyl]oxy}pentanoate (622404-99-3)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1002/hlca.200390151

upstream raw materials:

(3R,4R)-4-(benzyloxy)-3-{[(tert-butyl)dimethylsilyl]oxy}pentanoic acid

2-allyl-cyclohex-2-enone

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

(R)-2-benzyloxypropanal

Downstream raw materials:

(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

(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

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