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

Base Information

• Chemical Name: 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
• CAS No.: 112321-25-2
• Molecular Formula: C₂₄H₄₈O₆Si
• Molecular Weight: 460.727
• Mol file: 112321-25-2.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 27 articles about 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 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:

2-((1R,5S)-5-Isopropenyl-2-methyl-cyclohex-2-enyl)-propan-1-ol (112321-00-3,112419-70-2) → 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 (112321-25-2,112419-73-5)

Guidance literature:

Multi-step reaction with 12 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: 7 percent / zinc / ethanol; H₂O / 16 h / Heating

5: 83 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

6: 98 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

7: 95 percent / 1 N aq. NaOH, 30percent aq. H₂O₂ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

8: 69 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 1.) RT, 15 h, 2.) reflux, 15 h

9: 91 percent / LAH / diethyl ether / 1.5 h / 0 °C

10: 88 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.25 h / -50 °C

11: 55 percent / tetrahydrofuran / 1 h / -15 °C

12: sodium acetate, MCPBA / CH₂Cl₂ / 15 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; dihydrogen peroxide; sodium acetate; acetic anhydride; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; 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) → 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 (112321-25-2,112419-73-5)

Guidance literature:

Multi-step reaction with 11 steps

1: O₃ / CH₂Cl₂ / 0.2 h / -78 °C

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

3: 7 percent / zinc / ethanol; H₂O / 16 h / Heating

4: 83 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

5: 98 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

6: 95 percent / 1 N aq. NaOH, 30percent aq. H₂O₂ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

7: 69 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 1.) RT, 15 h, 2.) reflux, 15 h

8: 91 percent / LAH / diethyl ether / 1.5 h / 0 °C

9: 88 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.25 h / -50 °C

10: 55 percent / tetrahydrofuran / 1 h / -15 °C

11: sodium acetate, MCPBA / CH₂Cl₂ / 15 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; dihydrogen peroxide; sodium acetate; acetic anhydride; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water;

DOI:10.1021/jo00238a030

Reference yield:

1-((3R,3aR,5R,7S,7aS)-7-Bromo-3,7a-dimethyl-octahydro-benzofuran-5-yl)-1-methoxy-eth-1-yl-hydroperoxide (112347-68-9) → 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 (112321-25-2,112419-73-5)

Guidance literature:

Multi-step reaction with 10 steps

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

2: 7 percent / zinc / ethanol; H₂O / 16 h / Heating

3: 83 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

4: 98 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

5: 95 percent / 1 N aq. NaOH, 30percent aq. H₂O₂ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

6: 69 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 1.) RT, 15 h, 2.) reflux, 15 h

7: 91 percent / LAH / diethyl ether / 1.5 h / 0 °C

8: 88 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.25 h / -50 °C

9: 55 percent / tetrahydrofuran / 1 h / -15 °C

10: sodium acetate, MCPBA / CH₂Cl₂ / 15 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; dihydrogen peroxide; sodium acetate; acetic anhydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water;

DOI:10.1021/jo00238a030

upstream raw materials:

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

(3R,3aR,5R,7S,7aS)-2,3,3a,4,5,5,7,7a-octahydro-7-bromo-3,7a-dimethyl-5-(2-propenyl)-1-oxainden-2-one

2(R)-<2-methyl-5(S)-hydroxy-2-cyclohexen-1(R)-yl>propan-1-ol

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