(2S,4aS,5S,6S,8aS)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,8a-dimethyl-5-(4-methyl-pent-3-enyl)-octahydro-naphthalen-1-one

Base Information

Chemical Name:(2S,4aS,5S,6S,8aS)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,8a-dimethyl-5-(4-methyl-pent-3-enyl)-octahydro-naphthalen-1-one
CAS No.:153530-68-8
Molecular Formula:C₃₉H₅₅NO₄SSi
Molecular Weight:662.022
Hs Code.:

(2S,4aS,5S,6S,8aS)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,8a-dimethyl-5-(4-methyl-pent-3-enyl)-octahydro-naphthalen-1-one

Synonyms:(2S,4aS,5S,6S,8aS)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,8a-dimethyl-5-(4-methyl-pent-3-enyl)-octahydro-naphthalen-1-one

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Chemical Property of (2S,4aS,5S,6S,8aS)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,8a-dimethyl-5-(4-methyl-pent-3-enyl)-octahydro-naphthalen-1-one

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Technology Process of (2S,4aS,5S,6S,8aS)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,8a-dimethyl-5-(4-methyl-pent-3-enyl)-octahydro-naphthalen-1-one

There total 9 articles about (2S,4aS,5S,6S,8aS)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,8a-dimethyl-5-(4-methyl-pent-3-enyl)-octahydro-naphthalen-1-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: 97.0%

: (4aS,5S,6S,8aS)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,8a-dimethyl-5-(4-methyl-pent-3-enyl)-octahydro-naphthalen-1-one

: 153530-68-8
(2S,4aS,5S,6S,8aS)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,8a-dimethyl-5-(4-methyl-pent-3-enyl)-octahydro-naphthalen-1-one

Guidance literature:: With ammonium chloride; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)60131-4

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 153530-68-8
(2S,4aS,5S,6S,8aS)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,8a-dimethyl-5-(4-methyl-pent-3-enyl)-octahydro-naphthalen-1-one

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / 2,6-lutidine

2: 1.) BH₃-THF; 2.) H₂O₂, NaOH

3: 88 percent / Swern oxidation

4: 96 percent / n-BuLi / tetrahydrofuran / -78 - 0 °C

5: 94 percent / CSA / acetone

6: 66 percent / LiHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / Ambient temperature

7: 97 percent / LiHMDS, satd. aq. NH₄Cl / tetrahydrofuran

With 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; borane-THF; camphor-10-sulfonic acid; dihydrogen peroxide; ammonium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; acetone;
DOI:10.1016/S0040-4039(00)60131-4

Reference yield:

: 91547-51-2
(4aS,5S,8aS)-(+)-3,4,4a,7,8,8a-Hexahydro-5,8a-dimethyl-5-(prop-2-enyl)naphthalene-1,6(2H,5H)-dione 1-(Ethylene Acetal)

: 153530-68-8
(2S,4aS,5S,6S,8aS)-2-(1-Benzenesulfonyl-1H-indol-3-ylmethyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,8a-dimethyl-5-(4-methyl-pent-3-enyl)-octahydro-naphthalen-1-one

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / NaBH₄ / ethanol

2: 96 percent / 2,6-lutidine

3: 1.) BH₃-THF; 2.) H₂O₂, NaOH

4: 88 percent / Swern oxidation

5: 96 percent / n-BuLi / tetrahydrofuran / -78 - 0 °C

6: 94 percent / CSA / acetone

7: 66 percent / LiHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / Ambient temperature

8: 97 percent / LiHMDS, satd. aq. NH₄Cl / tetrahydrofuran

With 2,6-dimethylpyridine; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; borane-THF; camphor-10-sulfonic acid; dihydrogen peroxide; ammonium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; acetone;
DOI:10.1016/S0040-4039(00)60131-4