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

Base Information

• Chemical Name: (2R,4R,6S,9R,13S)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.0^4,9]hexadec-1⁽¹⁶⁾-ene-10,15-dione
• CAS No.: 184637-33-0
• Molecular Formula: C₂₈H₃₈O₅
• Molecular Weight: 454.607

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

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

Chemical Property:

Purity/Quality:

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

There total 7 articles about (2R,4R,6S,9R,13S)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-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: 95.0%

(2R,4R,6S,9R,13S,15R)-15-Hydroxy-2-methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.04,9]hexadec-1(16)-en-10-one (184637-32-9) → (2R,4R,6S,9R,13S)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.04,9]hexadec-1(16)-ene-10,15-dione (184637-33-0)

Guidance literature:

With Dess-Martin periodane; In pyridine; dichloromethane; for 1.5h;

DOI:10.1021/ja971527n

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,13S)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.04,9]hexadec-1(16)-ene-10,15-dione (184637-33-0)

Guidance literature:

Multi-step reaction with 6 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

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

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,13S)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.04,9]hexadec-1(16)-ene-10,15-dione (184637-33-0)

Guidance literature:

Multi-step reaction with 3 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

With Dess-Martin periodane; cesium fluoride; In pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja971527n

upstream raw materials:

(2R,4R,6S,9R,13S,15R)-15-Hydroxy-2-methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.0^4,9]hexadec-1⁽¹⁶⁾-en-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

C₃₀H₄₆O₅Si

Downstream raw materials:

(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

(3S,4aR,6R,7R,10S,13aR,14R)-7,14-epoxydodecahydro-6-methoxy-3-[(p-methoxybenzyl)oxy]-4,4,13a-trimethyl-9-methylene-7,10-methano-2H-benzocycloundecene-8,13-dione

(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

O-methylepoxyshikoccin

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