(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

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-1H-cyclopenta[a]pentalen-1-ol
CAS No.:110990-32-4
Molecular Formula:C₃₉H₄₈O₃Si
Molecular Weight:592.894
Hs Code.:

Synonyms:(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

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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-1H-cyclopenta[a]pentalen-1-ol

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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-1H-cyclopenta[a]pentalen-1-ol

There total 8 articles about (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 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: 95.0%

: 76-83-5
trityl chloride

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

: 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

Guidance literature:: With dmap; In N,N-dimethyl-formamide; at 70 ℃;
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

: 110990-32-4
(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

Guidance literature:: Multi-step reaction with 8 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

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

Reference yield:

: 110990-29-9
(2R,3bS,6aR,7aS)-2-Hydroxy-4,6a-dimethyl-2,3b,6,6a,7,7a-hexahydro-1H-cyclopenta[a]pentalene-3-carboxylic acid ethyl ester

: 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

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / imidazole / dimethylformamide / Ambient temperature

2: 60 percent / CrO₃, 3,5-DMP / CH₂Cl₂ / -25 °C

3: 85 percent / DIBAH / toluene

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

With 1H-imidazole; chromium(VI) oxide; dmap; diisobutylaluminium hydride; 3,5-Dimethylphenol; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)85180-1