[(1R,4S,5R,6R)-4-((S)-1,5-Dimethyl-hex-4-enyl)-6-[(Z)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enyl]-methanol

Base Information

Chemical Name:[(1R,4S,5R,6R)-4-((S)-1,5-Dimethyl-hex-4-enyl)-6-[(Z)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enyl]-methanol
CAS No.:110188-95-9
Molecular Formula:C₃₀H₅₀O₅
Molecular Weight:490.724
Hs Code.:

[(1R,4S,5R,6R)-4-((S)-1,5-Dimethyl-hex-4-enyl)-6-[(Z)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enyl]-methanol

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Chemical Property of [(1R,4S,5R,6R)-4-((S)-1,5-Dimethyl-hex-4-enyl)-6-[(Z)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enyl]-methanol

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Technology Process of [(1R,4S,5R,6R)-4-((S)-1,5-Dimethyl-hex-4-enyl)-6-[(Z)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enyl]-methanol

There total 2 articles about [(1R,4S,5R,6R)-4-((S)-1,5-Dimethyl-hex-4-enyl)-6-[(Z)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enyl]-methanol 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:

: (3aR,6S,7R,7aR)-6-((S)-1,5-Dimethyl-hex-4-enyl)-7-(tetrahydro-pyran-2-yloxymethyl)-3a,6,7,7a-tetrahydro-3H-isobenzofuran-1-one

: 52103-13-6
3-iodo-1-propanol tetrahydropyranyl ether triphenylphosphonium salt

: 110188-95-9,110222-77-0
[(1R,4S,5R,6R)-4-((S)-1,5-Dimethyl-hex-4-enyl)-6-[(Z)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enyl]-methanol

Guidance literature:: With potassium hexamethylsilazane; diisobutylaluminium hydride; Yield given. Multistep reaction; 1.) toluene, -78 deg C, 1h; 2.) DME-HMPA(2:1), 3h;
DOI:10.1016/S0040-4039(00)85070-4

Reference yield:

: (3aR,6S,7R,7aR)-6-((S)-1,5-Dimethyl-hex-4-enyl)-7-(tetrahydro-pyran-2-yloxymethyl)-3a,6,7,7a-tetrahydro-3H-isobenzofuran-1-one

: 52103-13-6
3-iodo-1-propanol tetrahydropyranyl ether triphenylphosphonium salt

: 110188-95-9,110222-77-0
[(1R,4S,5R,6R)-4-((S)-1,5-Dimethyl-hex-4-enyl)-6-[(Z)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enyl]-methanol

: [(1R,4S,5R,6S)-4-((S)-1,5-Dimethyl-hex-4-enyl)-6-[(Z)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enyl]-methanol

Guidance literature:: With potassium hexamethylsilazane; diisobutylaluminium hydride; Product distribution; 1.) toluene, -78 deg C, 1h; 2.) DME-HMPA (2:1), 3h; variation of ratio of phosphonium salt and solvents, reaction time and temperature;
DOI:10.1016/S0040-4039(00)85070-4

Reference yield:

: 110188-95-9,110222-77-0
[(1R,4S,5R,6R)-4-((S)-1,5-Dimethyl-hex-4-enyl)-6-[(Z)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enyl]-methanol

: 4-[(1S,2R,3R)-3-((S)-1,5-Dimethyl-hex-4-enyl)-2-hydroxymethyl-6-methylene-cyclohexyl]-butan-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) triethylamine and DMAP; 2.) MCPBA / 1.) CH₂Cl₂, 1h; 2.) CH₂Cl₂, 0 deg C

2: 1.) H₂(50 psi); 2.) KSeCN / 1.) 5percent Rh/Al₂O₃ / 1.) MeOH, 30 min; 2.) MeOH-H₂O(9:1), 65 deg C, 4d

3: 1.) o-nitrophenylselenocyanate-tributylphosphine; 2.) 30percent H₂O₂ / 1.) THF, 2h; 2.) THF, 1h

4: EtOH / PPTS / 10 h / 55 °C

With dmap; ortho-nitrophenyl selenocyanate; ethanol; tributylphosphine; hydrogen; dihydrogen peroxide; potassium selenocyanate; triethylamine; 3-chloro-benzenecarboperoxoic acid; Rh/Al₂O₃; pyridinium p-toluenesulfonate;
DOI:10.1016/S0040-4039(00)85070-4