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

Base Information

• Chemical Name: 3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2(R)-propyl>-1(R)-cyclohexanol
• CAS No.: 112321-12-7
• Molecular Formula: C₂₀H₄₂O₅Si
• Molecular Weight: 390.636
• Mol file: 112321-12-7.mol

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

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

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-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2(R)-propyl>-1(R)-cyclohexanol

There total 25 articles about 3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2(R)-propyl>-1(R)-cyclohexanol 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: 91.0%

3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2(R)-propyl>-cyclohexan-1(R)-yl benzoate (112321-11-6,112419-71-3) → 3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2(R)-propyl>-1(R)-cyclohexanol (112321-12-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 1.5h;

DOI:10.1021/jo00238a030

Reference yield: 55.0%

4-but-1-enylmagnesium bromide (7103-09-5) + 3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2(R)-propyl>-cyclohexan-1-one (112320-98-6) → 3(S)-<((2-methoxyethoxy)methyl)oxy>-4(S)-methyl-5(R)-<1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2(R)-propyl>-1(R)-cyclohexanol (112321-12-7) + 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 (112321-24-1)

Guidance literature:

In tetrahydrofuran; at -15 ℃; for 1h;

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-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2(R)-propyl>-1(R)-cyclohexanol (112321-12-7)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; dmap; sodium hydroxide; lithium aluminium tetrahydride; dihydrogen peroxide; acetic anhydride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water;

DOI:10.1021/jo00238a030

upstream raw materials:

4-but-1-enylmagnesium bromide

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>-cyclohexan-1(R)-yl benzoate

(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

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

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