(2R,4R,6S,9R,13R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-14-methylene-tricyclo[11.2.1.0^4,9]hexadec-1⁽¹⁶⁾-ene-10,15-dione

Base Information

• Chemical Name: (2R,4R,6S,9R,13R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-14-methylene-tricyclo[11.2.1.0^4,9]hexadec-1⁽¹⁶⁾-ene-10,15-dione
• CAS No.: 184637-34-1
• Molecular Formula: C₂₉H₃₈O₅
• Molecular Weight: 466.618

Synonyms:(2R,4R,6S,9R,13R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-14-methylene-tricyclo[11.2.1.0^4,9]hexadec-1⁽¹⁶⁾-ene-10,15-dione

Chemical Property of (2R,4R,6S,9R,13R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-14-methylene-tricyclo[11.2.1.0^4,9]hexadec-1⁽¹⁶⁾-ene-10,15-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (2R,4R,6S,9R,13R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-14-methylene-tricyclo[11.2.1.0^4,9]hexadec-1⁽¹⁶⁾-ene-10,15-dione

There total 9 articles about (2R,4R,6S,9R,13R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-14-methylene-tricyclo[11.2.1.0^4,9]hexadec-1⁽¹⁶⁾-ene-10,15-dione 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:

(1S,4'aR,6'S,8'aR)-4'a,5',6',7',8',8'a-hexahydro-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]spiro[2-cyclopentene-1,2'(1'H)-naphthalene]-1',3'(4'H)-dione → (2R,4R,6S,9R,13R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-14-methylene-tricyclo[11.2.1.04,9]hexadec-1(16)-ene-10,15-dione (184637-34-1)

Guidance literature:

Multi-step reaction with 8 steps

1: (i-Bu)2AlH / hexane; tetrahydrofuran / 1.5 h / -10 °C

2: 96 percent / Ag₂O, calcium sulfate / 20 h

3: 96 percent / tetrahydrofuran / 12 h / Ambient temperature

4: 87 percent / dimethylformamide / 16 h / 230 - 240 °C

5: CsF / dimethylformamide / 6 h / 210 °C

6: 95 percent / Dess-Martin periodinane reagent / CH₂Cl₂; pyridine / 1.5 h

7: potassium hexamethyldisilazide / toluene; tetrahydrofuran / 2 h / -78 °C

8: 2.) MeI, 3.) K₂CO₃ / 1) DMF, 50 deg C, 2.5 h; 2) ether, 24 h; 3) CH₂Cl₂, 24 h

With calcium sulfate; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; cesium fluoride; silver(l) oxide; methyl iodide; In tetrahydrofuran; pyridine; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja971527n

Reference yield:

(1R,1'S,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]-1'-vinylspiro(2-cyclopentene-1,2'(1'H)-naphthalene)-1'-ol (184637-31-8) → (2R,4R,6S,9R,13R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-14-methylene-tricyclo[11.2.1.04,9]hexadec-1(16)-ene-10,15-dione (184637-34-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / dimethylformamide / 16 h / 230 - 240 °C

2: CsF / dimethylformamide / 6 h / 210 °C

3: 95 percent / Dess-Martin periodinane reagent / CH₂Cl₂; pyridine / 1.5 h

4: potassium hexamethyldisilazide / toluene; tetrahydrofuran / 2 h / -78 °C

5: 2.) MeI, 3.) K₂CO₃ / 1) DMF, 50 deg C, 2.5 h; 2) ether, 24 h; 3) CH₂Cl₂, 24 h

With potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; cesium fluoride; methyl iodide; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja971527n

Reference yield:

(1R,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]spiro[2-cyclopentene-1,2'(1'H)-naphthalene]-1'-one (184637-36-3) → (2R,4R,6S,9R,13R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-14-methylene-tricyclo[11.2.1.04,9]hexadec-1(16)-ene-10,15-dione (184637-34-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / tetrahydrofuran / 12 h / Ambient temperature

2: 87 percent / dimethylformamide / 16 h / 230 - 240 °C

3: CsF / dimethylformamide / 6 h / 210 °C

4: 95 percent / Dess-Martin periodinane reagent / CH₂Cl₂; pyridine / 1.5 h

5: potassium hexamethyldisilazide / toluene; tetrahydrofuran / 2 h / -78 °C

6: 2.) MeI, 3.) K₂CO₃ / 1) DMF, 50 deg C, 2.5 h; 2) ether, 24 h; 3) CH₂Cl₂, 24 h

With potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; cesium fluoride; methyl iodide; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja971527n

upstream raw materials:

eschenmoser's salt

(2R,4R,6S,9R,13R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-15-trimethylsilanyloxy-tricyclo[11.2.1.0^4,9]hexadeca-1⁽¹⁶⁾,14-dien-10-one

(1R,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]spiro[2-cyclopentene-1,2'(1'H)-naphthalene]-1'-one

(1R,1'S,3'R,4'aR,5R,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-3'-methoxy-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]-1'-vinylspiro(2-cyclopentene-1,2'(1'H)-naphthalene)-1'-ol

Downstream raw materials:

O-methylshikoccin

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