(Z)-(2R,4R,6S,9R,13S,15S)-2,10-Dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.0^4,9]hexadeca-1⁽¹⁶⁾,10-dien-15-ol

Base Information

• Chemical Name: (Z)-(2R,4R,6S,9R,13S,15S)-2,10-Dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.0^4,9]hexadeca-1⁽¹⁶⁾,10-dien-15-ol
• CAS No.: 186087-63-8
• Molecular Formula: C₂₉H₄₂O₅
• Molecular Weight: 470.649

Synonyms:(Z)-(2R,4R,6S,9R,13S,15S)-2,10-Dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.0^4,9]hexadeca-1⁽¹⁶⁾,10-dien-15-ol

Chemical Property of (Z)-(2R,4R,6S,9R,13S,15S)-2,10-Dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.0^4,9]hexadeca-1⁽¹⁶⁾,10-dien-15-ol

Chemical Property:

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Technology Process of (Z)-(2R,4R,6S,9R,13S,15S)-2,10-Dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.0^4,9]hexadeca-1⁽¹⁶⁾,10-dien-15-ol

There total 5 articles about (Z)-(2R,4R,6S,9R,13S,15S)-2,10-Dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.0^4,9]hexadeca-1⁽¹⁶⁾,10-dien-15-ol 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: 25.0%

C34H54O5Si (186087-61-6) → (Z)-(2R,4R,6S,9R,13S,15S)-2,10-Dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.04,9]hexadeca-1(16),10-dien-15-ol (186087-63-8)

Guidance literature:

With N,N-dimethyl-formamide; cesium fluoride; at 210 ℃;

DOI:10.1016/S0040-4039(96)02247-2

Reference yield:

C32H48O5Si (186087-72-9) → (Z)-(2R,4R,6S,9R,13S,15S)-2,10-Dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.04,9]hexadeca-1(16),10-dien-15-ol (186087-63-8)

Guidance literature:

Multi-step reaction with 3 steps

1: LiAlH₄

2: 80 percent / NaH / tetrahydrofuran

3: 25 percent / 1.) DMF; 2.) CsF, DMF / 210 °C

With lithium aluminium tetrahydride; sodium hydride; N,N-dimethyl-formamide; cesium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(96)02247-2

Reference yield:

C30H46O5Si (184637-30-7) → (Z)-(2R,4R,6S,9R,13S,15S)-2,10-Dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.04,9]hexadeca-1(16),10-dien-15-ol (186087-63-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / tetrahydrofuran

2: periodinane / CH₂Cl₂

3: LiAlH₄

4: 80 percent / NaH / tetrahydrofuran

5: 25 percent / 1.) DMF; 2.) CsF, DMF / 210 °C

With lithium aluminium tetrahydride; sodium hydride; Dess-Martin periodane; N,N-dimethyl-formamide; cesium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(96)02247-2

upstream raw materials:

C₃₄H₅₄O₅Si

C₃₂H₄₈O₅Si

C₃₀H₄₆O₅Si

(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

Downstream raw materials:

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

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

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

[(Z)-(2R,4R,6S,9R,13R)-2,10-Dimethoxy-6-(4-methoxy-benzyloxy)-5,5,9-trimethyl-tricyclo[11.2.1.0^4,9]hexadeca-1⁽¹⁶⁾,10,14-trien-15-yloxy]-trimethyl-silane

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