(+)-(E)-((1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl)-2-((3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)acetate

Base Information

Chemical Name:(+)-(E)-((1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl)-2-((3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)acetate
CAS No.:873949-34-9
Molecular Formula:C₄₆H₇₄O₄Si₂
Molecular Weight:747.262
Hs Code.:

(+)-(E)-((1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl)-2-((3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)acetate

Synonyms:(+)-(E)-((1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl)-2-((3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)acetate

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Chemical Property of (+)-(E)-((1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl)-2-((3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)acetate

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Technology Process of (+)-(E)-((1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl)-2-((3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)acetate

There total 9 articles about (+)-(E)-((1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl)-2-((3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)acetate 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: 78.0%

: 146380-16-7
(-)-(3aR,4R,5R,6aR)-5-(tert-butyldimethylsilyloxy)-4-((3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyl-oct-1-en-6-ynyl)hexahydropentalene-2(1H)-one

: 200432-33-3
(1S,2R)-dimethoxyphosphanyl-2-(2-phenylpropan-2-yl)cyclohexyl 2-(dimethoxyphosphoryl)acetate

: (Z)-((1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl)-2-((3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)acetate

: 873949-34-9
(+)-(E)-((1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl)-2-((3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)acetate

Guidance literature:: (1S,2R)-dimethoxyphosphanyl-2-(2-phenylpropan-2-yl)cyclohexyl 2-(dimethoxyphosphoryl)acetate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃;

(-)-(3aR,4R,5R,6aR)-5-(tert-butyldimethylsilyloxy)-4-((3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyl-oct-1-en-6-ynyl)hexahydropentalene-2(1H)-one; In tetrahydrofuran; hexane; at -62 ℃; for 144h;
DOI:10.1021/ja0558037

Reference yield:

: 746651-66-1
(E)-(3S,4S)-4-Methyl-1-tributylstannanyl-oct-1-en-6-yn-3-ol

: 873949-34-9
(+)-(E)-((1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl)-2-((3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: imidazol / dimethylformamide

2.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -10 °C

3.1: 98 percent / aq. p-toluenesulfonic acid / acetone / 12 h / 20 °C

4.1: 1.04 g / imidazole / dimethylformamide / 14 h / 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

5.2: 78 percent / tetrahydrofuran; hexane / 144 h / -62 °C

With 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 6.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ja0558037

Reference yield:

: 873949-42-9
(-)-tert-butyldimethyl((3S,4S,E)-4-methyl-1-(tributylstannyl)oct-1-en-6-yn-3-yloxy)silane

: 873949-34-9
(+)-(E)-((1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl)-2-((3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((3S,4S,E)-3-(tert-butyldimethylsilyloxy)-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)acetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -10 °C

2.1: 98 percent / aq. p-toluenesulfonic acid / acetone / 12 h / 20 °C

3.1: 1.04 g / imidazole / dimethylformamide / 14 h / 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

4.2: 78 percent / tetrahydrofuran; hexane / 144 h / -62 °C

With 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 5.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ja0558037