(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

Base Information

• Chemical Name: (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
• CAS No.: 196939-49-8
• Molecular Formula: C₃₁H₄₆O₅Si
• Molecular Weight: 526.789

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

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Technology Process of (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

There total 8 articles about (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 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:

chloro-trimethyl-silane (75-77-4) + (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) → (2R,4R,6S,9R,13R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-15-trimethylsilanyloxy-tricyclo[11.2.1.04,9]hexadeca-1(16),14-dien-10-one (196939-49-8)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 2h;

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,13R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-15-trimethylsilanyloxy-tricyclo[11.2.1.04,9]hexadeca-1(16),14-dien-10-one (196939-49-8)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1021/ja971527n

Reference yield:

C30H46O5Si (184759-78-2) → (2R,4R,6S,9R,13R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-15-trimethylsilanyloxy-tricyclo[11.2.1.04,9]hexadeca-1(16),14-dien-10-one (196939-49-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / Ag₂O, calcium sulfate / 20 h

2: 96 percent / tetrahydrofuran / 12 h / Ambient temperature

3: 87 percent / dimethylformamide / 16 h / 230 - 240 °C

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

5: 95 percent / Dess-Martin periodinane reagent / CH₂Cl₂; pyridine / 1.5 h

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

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

DOI:10.1021/ja971527n

upstream raw materials:

chloro-trimethyl-silane

(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

(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-methylepoxyshikoccin

O-methylshikoccin

(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

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