4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-ol

Base Information

• Chemical Name: 4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-ol
• CAS No.: 112321-18-3
• Molecular Formula: C₁₅H₂₆O₃
• Molecular Weight: 254.37
• Mol file: 112321-18-3.mol

Synonyms:4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-ol

Chemical Property of 4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-ol

There total 8 articles about 4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-ol 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: 100.0%

4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-yl acetate (112321-17-2) → 4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-ol (112321-18-3)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 2h;

DOI:10.1021/jo00238a030

Reference yield:

6(R)-1(S),7(R)-dimethyl-2(S)-bromo-4(R)-(2-propenyl)-9-oxabicyclo<4.3.0>nonane (112347-67-8) → 4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-ol (112321-18-3)

Guidance literature:

Multi-step reaction with 5 steps

1: O₃ / CH₂Cl₂ / 0.2 h / -78 °C

2: acetic anhydride, Et₃N, (N,N-dimethylamino)pyridine / CH₂Cl₂ / 16 h / 40 °C

3: 87 percent / zinc / ethanol; H₂O / 16 h / Heating

4: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h

5: 100 percent / LAH / diethyl ether / 2 h / 0 °C

With dmap; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; acetic anhydride; ozone; triethylamine; zinc; In diethyl ether; ethanol; dichloromethane; water;

DOI:10.1021/jo00238a030

Reference yield:

2-((1R,5S)-5-Isopropenyl-2-methyl-cyclohex-2-enyl)-propan-1-ol (112321-00-3,112419-70-2) → 4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-ol (112321-18-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / N-bromosuccinimide / acetone / 0.25 h / 0 °C

2: O₃ / CH₂Cl₂ / 0.2 h / -78 °C

3: acetic anhydride, Et₃N, (N,N-dimethylamino)pyridine / CH₂Cl₂ / 16 h / 40 °C

4: 87 percent / zinc / ethanol; H₂O / 16 h / Heating

5: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h

6: 100 percent / LAH / diethyl ether / 2 h / 0 °C

With dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; acetic anhydride; ozone; triethylamine; zinc; In diethyl ether; ethanol; dichloromethane; water; acetone;

DOI:10.1021/jo00238a030

upstream raw materials:

4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-yl acetate

3,4-dihydro-2H-pyran

6(R)-1(S),7(R)-dimethyl-2(S)-bromo-4(R)-(2-propenyl)-9-oxabicyclo<4.3.0>nonane

1-((3R,3aR,5R,7S,7aS)-7-Bromo-3,7a-dimethyl-octahydro-benzofuran-5-yl)-1-methoxy-eth-1-yl-hydroperoxide

Downstream raw materials:

4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-one

tetrahydro-2-(benzyloxy)-2H-pyran

(5S)-1(S)-(benzyloxy)-3(S)-hydroxy-4(S),6(R)-dimethyl-8-oxabicyclo<3.3.1>nonane

3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-hydroxy-2(R)-propyl>cyclohexan-1-one