(3R,3aS,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-1-oxo-4-trityloxymethyl-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalene-3-carbaldehyde

Base Information

• Chemical Name: (3R,3aS,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-1-oxo-4-trityloxymethyl-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalene-3-carbaldehyde
• CAS No.: 110990-39-1
• Molecular Formula: C₄₀H₄₈O₄Si
• Molecular Weight: 620.904
• Mol file: 110990-39-1.mol

Synonyms:(3R,3aS,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-1-oxo-4-trityloxymethyl-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalene-3-carbaldehyde

Chemical Property of (3R,3aS,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-1-oxo-4-trityloxymethyl-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalene-3-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3aS,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-1-oxo-4-trityloxymethyl-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalene-3-carbaldehyde

There total 13 articles about (3R,3aS,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-1-oxo-4-trityloxymethyl-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalene-3-carbaldehyde 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:

trityl chloride (76-83-5) → (3R,3aS,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-1-oxo-4-trityloxymethyl-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalene-3-carbaldehyde (110990-39-1)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 86 percent / BF₃*Et₂O / tetrahydrofuran; diethyl ether / -50 °C

4: NMO / osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol

5: NaIO₄ / dioxane; H₂O

With dmap; manganese(IV) oxide; sodium periodate; N-methyl-2-indolinone; boron trifluoride diethyl etherate; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; chloroform; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)85180-1

Reference yield:

(1R*,5R*)-5,8-dimethyl-cis-bicyclo<3.3.0>oct-7-en-2-one (54931-38-3,101198-90-7,134053-16-0) → (3R,3aS,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-1-oxo-4-trityloxymethyl-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalene-3-carbaldehyde (110990-39-1)

Guidance literature:

Multi-step reaction with 12 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

10: 86 percent / BF₃*Et₂O / tetrahydrofuran; diethyl ether / -50 °C

11: NMO / osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol

12: NaIO₄ / dioxane; H₂O

With 1H-imidazole; chromium(VI) oxide; dmap; manganese(IV) oxide; sodium tetrahydroborate; sodium periodate; perchloric acid; N-methyl-2-indolinone; cerium(III) chloride; boron trifluoride diethyl etherate; sodium ethanolate; diisobutylaluminium hydride; 3,5-Dimethylphenol; lithium diisopropyl amide; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)85180-1

Reference yield:

(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 (110990-29-9) → (3R,3aS,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3,7a-dimethyl-1-oxo-4-trityloxymethyl-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalene-3-carbaldehyde (110990-39-1)

Guidance literature:

Multi-step reaction with 8 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

5: 94 percent / act. MnO₂ / CHCl₃ / Ambient temperature

6: 86 percent / BF₃*Et₂O / tetrahydrofuran; diethyl ether / -50 °C

7: NMO / osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol

8: NaIO₄ / dioxane; H₂O

With 1H-imidazole; chromium(VI) oxide; dmap; manganese(IV) oxide; sodium periodate; N-methyl-2-indolinone; boron trifluoride diethyl etherate; diisobutylaluminium hydride; 3,5-Dimethylphenol; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)85180-1

upstream raw materials:

trityl chloride

(1R*,5R*)-5,8-dimethyl-cis-bicyclo<3.3.0>oct-7-en-2-one

(3bS,6aR,7aS)-4,6a-Dimethyl-2-oxo-2,3b,6,6a,7,7a-hexahydro-1H-cyclopenta[a]pentalene-3-carboxylic acid ethyl ester

(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

Downstream raw materials:

(1S,3R,3aS,5S,6aR,7aS)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3,7a-dimethyl-4-trityloxymethyl-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalene

(2S,3R,3aR,3bS,4R,6S,6aS,7aR)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4,6a-dimethyl-3-trityloxymethyl-decahydro-cyclopenta[a]pentalene-3,3a-diol