(2R,5aS,7R,9S,9aS)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-1,2,5,5a,6,7,8,9-octahydro-cyclopenta[c]inden-4-one

Base Information

Chemical Name:(2R,5aS,7R,9S,9aS)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-1,2,5,5a,6,7,8,9-octahydro-cyclopenta[c]inden-4-one
CAS No.:251651-00-0
Molecular Formula:C₂₇H₄₀O₃Si
Molecular Weight:440.698
Hs Code.:

Synonyms:(2R,5aS,7R,9S,9aS)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-1,2,5,5a,6,7,8,9-octahydro-cyclopenta[c]inden-4-one

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Chemical Property of (2R,5aS,7R,9S,9aS)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-1,2,5,5a,6,7,8,9-octahydro-cyclopenta[c]inden-4-one

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Technology Process of (2R,5aS,7R,9S,9aS)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-1,2,5,5a,6,7,8,9-octahydro-cyclopenta[c]inden-4-one

There total 12 articles about (2R,5aS,7R,9S,9aS)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-1,2,5,5a,6,7,8,9-octahydro-cyclopenta[c]inden-4-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:

: (R)-2-[(E)-3-(Dimethyl-phenyl-silanyl)-allyl]-5-methyl-cyclohex-2-enone

: 251651-00-0
(2R,5aS,7R,9S,9aS)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-1,2,5,5a,6,7,8,9-octahydro-cyclopenta[c]inden-4-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: CuI

2.1: NaI; mCPBA

3.1: 82 percent / Bu₃SnH; AIBN / benzene / Heating

4.1: Li; NH₃

5.1: TBAF

5.2: KHCO₃; H₂O₂ / methanol

6.1: 95 percent / imidazole

7.1: 90 percent / PCC

8.1: 88 percent / L-Selectride

9.1: 87 percent / KH / tetrahydrofuran

10.1: 82 percent / CF₃COOH

11.1: SeO₂ / dioxane

With 1H-imidazole; copper(l) iodide; selenium(IV) oxide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; ammonia; tri-n-butyl-tin hydride; lithium; potassium hydride; L-Selectride; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; 1,4-dioxane; benzene; 1.1: addition; silylation / 2.1: Iodination / 3.1: Cyclization / 4.1: Reduction / 5.1: Substitution / 5.2: Oxidation / 6.1: silylation / 7.1: Oxidation / 8.1: Reduction / 9.1: benzylation / 10.1: desilylation / 11.1: allylic oxidation / 12.1: Swern oxidation;
DOI:10.1021/ja992315o

Reference yield:

: 251650-95-0
(2S,5aR,7R,9R,9aS)-2-Hydroxymethyl-7-methyl-3-trimethylsilanyl-2,4,5,5a,6,7,8,9-octahydro-1H-cyclopenta[c]inden-9-ol

: 251651-00-0
(2R,5aS,7R,9S,9aS)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-1,2,5,5a,6,7,8,9-octahydro-cyclopenta[c]inden-4-one

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / imidazole

2: 90 percent / PCC

3: 88 percent / L-Selectride

4: 87 percent / KH / tetrahydrofuran

5: 82 percent / CF₃COOH

6: SeO₂ / dioxane

With 1H-imidazole; selenium(IV) oxide; potassium hydride; L-Selectride; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; 1: silylation / 2: Oxidation / 3: Reduction / 4: benzylation / 5: desilylation / 6: allylic oxidation / 7: Swern oxidation;
DOI:10.1021/ja992315o

Reference yield:

: 251650-99-4
(9-benzyloxy-7-methyl-2,4,5,5a,6,7,8,9-octahydro-1H-cyclopenta[c]inden-2-ylmethoxy)-tert-butyl-dimethyl-silane

: 251651-00-0
(2R,5aS,7R,9S,9aS)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-1,2,5,5a,6,7,8,9-octahydro-cyclopenta[c]inden-4-one

Guidance literature:: Multi-step reaction with 2 steps

1: SeO₂ / dioxane

With selenium(IV) oxide; In 1,4-dioxane; 1: allylic oxidation / 2: Swern oxidation;
DOI:10.1021/ja992315o