Acetic acid (S)-1-hydroxy-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-cyclohex-3-enylmethyl ester

Base Information

• Chemical Name: Acetic acid (S)-1-hydroxy-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-cyclohex-3-enylmethyl ester
• CAS No.: 810682-17-8
• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.439
• Mol file: 810682-17-8.mol

Synonyms:Acetic acid (S)-1-hydroxy-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-cyclohex-3-enylmethyl ester

Chemical Property of Acetic acid (S)-1-hydroxy-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-cyclohex-3-enylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (S)-1-hydroxy-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-cyclohex-3-enylmethyl ester

There total 11 articles about Acetic acid (S)-1-hydroxy-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-cyclohex-3-enylmethyl ester 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%

acetic anhydride (108-24-7) + (S)-1-Hydroxymethyl-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-cyclohex-3-enol (810682-43-0) → Acetic acid (S)-1-hydroxy-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-cyclohex-3-enylmethyl ester (810682-17-8)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 0.333333h;

DOI:10.1016/j.tetlet.2004.09.143

Reference yield:

(S)-3-hydroxy-2,2-dimethylcyclohexanone (87655-21-8) → Acetic acid (S)-1-hydroxy-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-cyclohex-3-enylmethyl ester (810682-17-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 96 percent / imidazole / CH₂Cl₂ / 1.5 h

2.1: 50 percent / SmI₂; HMPA / tetrahydrofuran / 0.25 h / -78 °C

3.1: aq. H₂O₂; KHCO₃; KF / tetrahydrofuran; methanol / 10 h

4.1: CSA / 1 h

5.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

6.1: LDA; Eschenmoser's salt / tetrahydrofuran / 1 h / -78 - 0 °C

6.2: 64 percent / acetone / 10 h

7.1: 96 percent / NaBH₄ / CeCl₃*7H₂O / methanol / 0.08 h

8.1: 84 percent / SOCl₂; pyridine / diethyl ether / 3 h

9.1: 92 percent / TBAI / tetrahydrofuran; dimethylformamide / 5 h / 60 °C

10.1: 98 percent / PTSA / methanol; H₂O / 3 h / 50 °C

11.1: 91 percent / pyridine; DMAP / CH₂Cl₂ / 0.33 h

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium fluoride; sodium tetrahydroborate; thionyl chloride; samarium diiodide; dihydrogen peroxide; eschenmoser's salt; tetra-(n-butyl)ammonium iodide; potassium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; lithium diisopropyl amide; cerium(III) chloride; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 3.1: Tamao oxidation / 5.1: Dess-Martin oxidation / 7.1: Luche reduction;

DOI:10.1016/j.tetlet.2004.09.143

Reference yield:

(1S,3S)-1-Hydroxymethyl-2,2-dimethyl-cyclohexane-1,3-diol (954096-32-3) → Acetic acid (S)-1-hydroxy-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-cyclohex-3-enylmethyl ester (810682-17-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: CSA / 1 h

2.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

3.1: LDA; Eschenmoser's salt / tetrahydrofuran / 1 h / -78 - 0 °C

3.2: 64 percent / acetone / 10 h

4.1: 96 percent / NaBH₄ / CeCl₃*7H₂O / methanol / 0.08 h

5.1: 84 percent / SOCl₂; pyridine / diethyl ether / 3 h

6.1: 92 percent / TBAI / tetrahydrofuran; dimethylformamide / 5 h / 60 °C

7.1: 98 percent / PTSA / methanol; H₂O / 3 h / 50 °C

8.1: 91 percent / pyridine; DMAP / CH₂Cl₂ / 0.33 h

With pyridine; dmap; sodium tetrahydroborate; thionyl chloride; eschenmoser's salt; tetra-(n-butyl)ammonium iodide; Dess-Martin periodane; toluene-4-sulfonic acid; lithium diisopropyl amide; cerium(III) chloride; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 2.1: Dess-Martin oxidation / 4.1: Luche reduction;

DOI:10.1016/j.tetlet.2004.09.143

upstream raw materials:

acetic anhydride

(S)-1-Hydroxymethyl-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-cyclohex-3-enol

(S)-3-hydroxy-2,2-dimethylcyclohexanone

(1S,3S)-1-Hydroxymethyl-2,2-dimethyl-cyclohexane-1,3-diol

Downstream raw materials:

Acetic acid (S)-4-(4-methoxy-benzyloxymethyl)-1-methoxymethoxy-2,2-dimethyl-cyclohex-3-enylmethyl ester

[(S)-4-(4-Methoxy-benzyloxymethyl)-1-methoxymethoxy-2,2-dimethyl-cyclohex-3-enyl]-methanol