(3aR,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-4-trityloxymethyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-1-one

Base Information

Chemical Name:(3aR,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-4-trityloxymethyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-1-one
CAS No.:110990-33-5
Molecular Formula:C₃₉H₄₆O₃Si
Molecular Weight:590.878
Hs Code.:

Synonyms:(3aR,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-4-trityloxymethyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-1-one

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Chemical Property of (3aR,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-4-trityloxymethyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-1-one

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Technology Process of (3aR,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-4-trityloxymethyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-1-one

There total 10 articles about (3aR,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-4-trityloxymethyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-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: 94.0%

: 110990-32-4
(3aR,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-4-trityloxymethyl-3a,5,6,6a,7,7a-hexahydro-1H-cyclopenta[a]pentalen-1-ol

: 110990-33-5
(3aR,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-4-trityloxymethyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-1-one

Guidance literature:: With manganese(IV) oxide; In chloroform; Ambient temperature;
DOI:10.1016/S0040-4039(00)85180-1

Reference yield:

: 76-83-5
trityl chloride

: 110990-33-5
(3aR,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-4-trityloxymethyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-1-one

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / 4-DMAP / dimethylformamide / 70 °C

2: 94 percent / act. MnO₂ / CHCl₃ / Ambient temperature

With dmap; manganese(IV) oxide; In chloroform; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)85180-1

Reference yield:

: 54931-38-3,101198-90-7,134053-16-0
(1R*,5R*)-5,8-dimethyl-cis-bicyclo<3.3.0>oct-7-en-2-one

: 110990-33-5
(3aR,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-4-trityloxymethyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-1-one

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) LDA / 1.) THF, -78 deg C,

2: 90 percent / 30 percent aq. perchloric acid / diethyl ether / Ambient temperature

3: 85 percent / sodium ethoxide / ethanol / Ambient temperature

4: 70 percent / NaBH₄, CeCl₃*7H₂O / methanol

5: 98 percent / imidazole / dimethylformamide / Ambient temperature

6: 60 percent / CrO₃, 3,5-DMP / CH₂Cl₂ / -25 °C

7: 85 percent / DIBAH / toluene

8: 95 percent / 4-DMAP / dimethylformamide / 70 °C

9: 94 percent / act. MnO₂ / CHCl₃ / Ambient temperature

With 1H-imidazole; chromium(VI) oxide; dmap; manganese(IV) oxide; sodium tetrahydroborate; perchloric acid; cerium(III) chloride; sodium ethanolate; diisobutylaluminium hydride; 3,5-Dimethylphenol; lithium diisopropyl amide; In methanol; diethyl ether; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)85180-1