(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

Base Information

• Chemical Name: (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
• CAS No.: 110990-40-4
• Molecular Formula: C₅₂H₈₀O₄Si₃
• Molecular Weight: 853.461
• Mol file: 110990-40-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 15 articles about (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 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: 98.0%

(1S,3R,3aS,5S,6aR,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxymethyl-3,7a-dimethyl-4-trityloxymethyl-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-1-ol + tert-butyldimethylsilyl chloride (18162-48-6) → (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 (110990-40-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;

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

Reference yield:

trityl chloride (76-83-5) → (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 (110990-40-4)

Guidance literature:

Multi-step reaction with 7 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

6: 85 percent / L-Selectride / tetrahydrofuran / 0 °C

7: 98 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; dmap; manganese(IV) oxide; sodium periodate; N-methyl-2-indolinone; boron trifluoride diethyl etherate; L-Selectride; 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) → (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 (110990-40-4)

Guidance literature:

Multi-step reaction with 14 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

13: 85 percent / L-Selectride / tetrahydrofuran / 0 °C

14: 98 percent / imidazole / dimethylformamide / Ambient temperature

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; L-Selectride; 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

upstream raw materials:

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

(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