(2R,4R,6S,9R,13S,15S)-2-Hydroxy-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

Base Information

• Chemical Name: (2R,4R,6S,9R,13S,15S)-2-Hydroxy-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
• CAS No.: 196939-47-6
• Molecular Formula: C₃₂H₅₀O₅Si
• Molecular Weight: 542.832

Synonyms:(2R,4R,6S,9R,13S,15S)-2-Hydroxy-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

Chemical Property of (2R,4R,6S,9R,13S,15S)-2-Hydroxy-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

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Technology Process of (2R,4R,6S,9R,13S,15S)-2-Hydroxy-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

There total 5 articles about (2R,4R,6S,9R,13S,15S)-2-Hydroxy-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 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: 54.0%

(1R,1'R,3'R,4'aR,6'S,8'aR)-3',4',4'a,5',6',7',8',8'a-octahydro-6'-[(p-methoxybenzyl)oxy]-5',5',8'a-trimethyl-5-[2-(trimethylsilyl)ethoxy]-1'-vinylspiro(2-cyclopentene-1,2'(1'H)-naphthalene)-1',3'-diol (186087-73-0) → (2R,4R,6S,9R,13S,15S)-2-Hydroxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-15-(2-trimethylsilanyl-ethoxy)-tricyclo[11.2.1.04,9]hexadec-1(16)-en-10-one (196939-47-6)

Guidance literature:

In N,N-dimethyl-formamide; at 230 ℃; for 3h;

DOI:10.1021/ja971527n

Reference yield:

C32H48O5Si (186087-72-9) → (2R,4R,6S,9R,13S,15S)-2-Hydroxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-15-(2-trimethylsilanyl-ethoxy)-tricyclo[11.2.1.04,9]hexadec-1(16)-en-10-one (196939-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / tetrahydrofuran / 2 h / -78 °C

2: 54 percent / dimethylformamide / 3 h / 230 °C

With lithium aluminium tetrahydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja971527n

Reference yield:

C30H46O5Si (184637-30-7) → (2R,4R,6S,9R,13S,15S)-2-Hydroxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-15-(2-trimethylsilanyl-ethoxy)-tricyclo[11.2.1.04,9]hexadec-1(16)-en-10-one (196939-47-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / tetrahydrofuran / 12 h / 20 °C

2: Dess-Martin periodinane reagent / CH₂Cl₂; pyridine / 2 h

3: LiAlH₄ / tetrahydrofuran / 2 h / -78 °C

4: 54 percent / dimethylformamide / 3 h / 230 °C

With lithium aluminium tetrahydride; Dess-Martin periodane; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja971527n

upstream raw materials:

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

C₃₂H₄₈O₅Si

C₃₀H₄₆O₅Si

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

Downstream raw materials:

(2R,4R,6S,9R,13S,15S)-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

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