(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

Base Information

• Chemical Name: (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
• CAS No.: 184637-32-9
• Molecular Formula: C₂₈H₄₀O₅
• Molecular Weight: 456.623

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 6 articles about (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 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:

(2R,4R,6S,9R,13S,15R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-15-(2-trimethylsilanyl-ethoxy)-tricyclo[11.2.1.04,9]hexadec-1(16)-en-10-one (196939-45-4) → (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)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide; at 210 ℃; for 6h; Yield given;

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,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)

Guidance literature:

Multi-step reaction with 5 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

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

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,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)

Guidance literature:

Multi-step reaction with 3 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

With cesium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja971527n

upstream raw materials:

(2R,4R,6S,9R,13S,15R)-2-Methoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-15-(2-trimethylsilanyl-ethoxy)-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,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

O-methylshikoccin

O-methylepoxyshikoccin

(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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