(1R,2S,3S,4R,6R)-3-Benzyloxy-4-methyl-6-(naphthalen-1-ylmethoxy)-cyclohexane-1,2-diol

Base Information

• Chemical Name: (1R,2S,3S,4R,6R)-3-Benzyloxy-4-methyl-6-(naphthalen-1-ylmethoxy)-cyclohexane-1,2-diol
• CAS No.: 1053628-62-8
• Molecular Formula: C₂₅H₂₈O₄
• Molecular Weight: 392.495
• Mol file: 1053628-62-8.mol

Synonyms:

Chemical Property of (1R,2S,3S,4R,6R)-3-Benzyloxy-4-methyl-6-(naphthalen-1-ylmethoxy)-cyclohexane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3S,4R,6R)-3-Benzyloxy-4-methyl-6-(naphthalen-1-ylmethoxy)-cyclohexane-1,2-diol

There total 9 articles about (1R,2S,3S,4R,6R)-3-Benzyloxy-4-methyl-6-(naphthalen-1-ylmethoxy)-cyclohexane-1,2-diol 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:

D-(-)-quinic acid (77-95-2) → (1R,2S,3S,4R,6R)-3-Benzyloxy-4-methyl-6-(naphthalen-1-ylmethoxy)-cyclohexane-1,2-diol (1053628-62-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: H₂SO₄ / 20 °C

2.1: pyridine / CH₂Cl₂ / -20 °C

3.1: SOCl₂ / 0 - 20 °C

4.1: H₂SO₄ / methanol / 20 °C

5.1: p-toluenesulfonic acid / dioxane / 3 h / 60 °C

6.1: 78 percent / DIBALH / tetrahydrofuran / 0 °C

7.1: 93 percent / CBr₄; PPh₃; syn-collidine / 20 °C

8.1: 92 percent / lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C

9.1: 85 percent / KOH; 18-crown-6 / tetrahydrofuran / 20 °C

10.1: 9-BBN / tetrahydrofuran / Heating

10.2: aq. NaOH; H₂O₂ / tetrahydrofuran / 0 - 20 °C

11.1: 89 percent / KOH; 18-crown-6 / tetrahydrofuran / 20 °C

12.1: 87 percent / aq. TFA / CH₂Cl₂ / 20 °C

With pyridine; 2,4,6-trimethyl-pyridine; potassium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; thionyl chloride; 18-crown-6 ether; carbon tetrabromide; sulfuric acid; diisobutylaluminium hydride; lithium triethylborohydride; toluene-4-sulfonic acid; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1055/s-2004-834825

Reference yield:

3,4,5-tri-O-acetyl quinate de methyle (50605-62-4,51064-54-1) → (1R,2S,3S,4R,6R)-3-Benzyloxy-4-methyl-6-(naphthalen-1-ylmethoxy)-cyclohexane-1,2-diol (1053628-62-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: SOCl₂ / 0 - 20 °C

2.1: H₂SO₄ / methanol / 20 °C

3.1: p-toluenesulfonic acid / dioxane / 3 h / 60 °C

4.1: 78 percent / DIBALH / tetrahydrofuran / 0 °C

5.1: 93 percent / CBr₄; PPh₃; syn-collidine / 20 °C

6.1: 92 percent / lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C

7.1: 85 percent / KOH; 18-crown-6 / tetrahydrofuran / 20 °C

8.1: 9-BBN / tetrahydrofuran / Heating

8.2: aq. NaOH; H₂O₂ / tetrahydrofuran / 0 - 20 °C

9.1: 89 percent / KOH; 18-crown-6 / tetrahydrofuran / 20 °C

10.1: 87 percent / aq. TFA / CH₂Cl₂ / 20 °C

With 2,4,6-trimethyl-pyridine; potassium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; thionyl chloride; 18-crown-6 ether; carbon tetrabromide; sulfuric acid; diisobutylaluminium hydride; lithium triethylborohydride; toluene-4-sulfonic acid; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1055/s-2004-834825

Reference yield:

methyl (-)-quinate (191916-39-9) → (1R,2S,3S,4R,6R)-3-Benzyloxy-4-methyl-6-(naphthalen-1-ylmethoxy)-cyclohexane-1,2-diol (1053628-62-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: pyridine / CH₂Cl₂ / -20 °C

2.1: SOCl₂ / 0 - 20 °C

3.1: H₂SO₄ / methanol / 20 °C

4.1: p-toluenesulfonic acid / dioxane / 3 h / 60 °C

5.1: 78 percent / DIBALH / tetrahydrofuran / 0 °C

6.1: 93 percent / CBr₄; PPh₃; syn-collidine / 20 °C

7.1: 92 percent / lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C

8.1: 85 percent / KOH; 18-crown-6 / tetrahydrofuran / 20 °C

9.1: 9-BBN / tetrahydrofuran / Heating

9.2: aq. NaOH; H₂O₂ / tetrahydrofuran / 0 - 20 °C

10.1: 89 percent / KOH; 18-crown-6 / tetrahydrofuran / 20 °C

11.1: 87 percent / aq. TFA / CH₂Cl₂ / 20 °C

With pyridine; 2,4,6-trimethyl-pyridine; potassium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; thionyl chloride; 18-crown-6 ether; carbon tetrabromide; sulfuric acid; diisobutylaluminium hydride; lithium triethylborohydride; toluene-4-sulfonic acid; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1055/s-2004-834825

upstream raw materials:

D-(-)-quinic acid

3,4,5-tri-O-acetyl quinate de methyle

methyl (-)-quinate

methyl (3aS,4R,7aR)-4-hydroxy-3a,4,5,7a-tetrahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-6-carboxylate