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

Base Information

• Chemical Name: 3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-hydroxy-2(R)-propyl>cyclohexan-1-one
• CAS No.: 112347-69-0
• Molecular Formula: C₁₄H₂₆O₅
• Molecular Weight: 274.357
• Mol file: 112347-69-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-hydroxy-2(R)-propyl>cyclohexan-1-one 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: 99.0%

(5S)-1(S)-(benzyloxy)-3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S),6(R)-dimethyl-8-oxabicyclo<3.3.1>nonane (112321-21-8) → 3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-hydroxy-2(R)-propyl>cyclohexan-1-one (112347-69-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 4.5h; Ambient temperature;

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) → 3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-hydroxy-2(R)-propyl>cyclohexan-1-one (112347-69-0)

Guidance literature:

Multi-step reaction with 10 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

7: 91 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.25 h / -50 °C

9: 1.) KH / 1.) THF, RT, 10 min, 2.) RT, 90 min

10: 99 percent / H₂ / 10percent Pd/C / ethanol / 4.5 h / Ambient temperature

With dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; pyridinium p-toluenesulfonate; acetic anhydride; potassium hydride; ozone; dimethyl sulfoxide; triethylamine; zinc; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; water; acetone;

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) → 3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-hydroxy-2(R)-propyl>cyclohexan-1-one (112347-69-0)

Guidance literature:

Multi-step reaction with 9 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

6: 91 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.25 h / -50 °C

8: 1.) KH / 1.) THF, RT, 10 min, 2.) RT, 90 min

9: 99 percent / H₂ / 10percent Pd/C / ethanol / 4.5 h / Ambient temperature

With dmap; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; pyridinium p-toluenesulfonate; acetic anhydride; potassium hydride; ozone; dimethyl sulfoxide; triethylamine; zinc; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; water;

DOI:10.1021/jo00238a030

upstream raw materials:

(5S)-1(S)-(benzyloxy)-3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S),6(R)-dimethyl-8-oxabicyclo<3.3.1>nonane

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

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

Downstream raw materials:

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

3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2(R)-propyl>-1(R)-cyclohexanol

1(S)-(3,4-epoxy-1-butyl)-3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2(R)-propyl>-cyclohexan-1-ol

1(S)-(4-buten-1-yl)-3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2(R)-propyl>-cyclohexan-1-ol