(-)-(6aR,8S,9R,9aR)-8-(benzyloxy)-2,2,4,4-tetraisopropyl-7-methyleneperhydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-ol

Base Information

• Chemical Name: (-)-(6aR,8S,9R,9aR)-8-(benzyloxy)-2,2,4,4-tetraisopropyl-7-methyleneperhydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-ol
• CAS No.: 1307273-62-6
• Molecular Formula: C₂₆H₄₄O₅Si₂
• Molecular Weight: 492.803
• Mol file: 1307273-62-6.mol

Synonyms:(-)-(6aR,8S,9R,9aR)-8-(benzyloxy)-2,2,4,4-tetraisopropyl-7-methyleneperhydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-ol

Chemical Property of (-)-(6aR,8S,9R,9aR)-8-(benzyloxy)-2,2,4,4-tetraisopropyl-7-methyleneperhydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(6aR,8S,9R,9aR)-8-(benzyloxy)-2,2,4,4-tetraisopropyl-7-methyleneperhydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-ol

There total 6 articles about (-)-(6aR,8S,9R,9aR)-8-(benzyloxy)-2,2,4,4-tetraisopropyl-7-methyleneperhydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-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: 81.0%

(-)-(6aR,8S,9S,9aR)-8-(benzyloxy)-2,2,4,4-tetraisopropyl-7-methylenehexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-ol (1307273-61-5) → (-)-(6aR,8S,9R,9aR)-8-(benzyloxy)-2,2,4,4-tetraisopropyl-7-methyleneperhydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-ol (1307273-62-6)

Guidance literature:

(-)-(6aR,8S,9S,9aR)-8-(benzyloxy)-2,2,4,4-tetraisopropyl-7-methylenehexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-ol; With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -78 - 20 ℃; for 0.333333h;

With cesium acetate; 18-crown-6 ether; In benzene; at 50 ℃; for 0.5h;

With sodium methylate; In methanol; at 20 ℃; for 3h;

Reference yield:

(3aR,6R,6aR)-6-(tert-butoxymethyl)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-one (223596-25-6) → (-)-(6aR,8S,9R,9aR)-8-(benzyloxy)-2,2,4,4-tetraisopropyl-7-methyleneperhydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-ol (1307273-62-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 3 h / -78 °C

1.2: -78 - 20 °C

1.3: 4 h / 20 °C

2.1: cerium(III) chloride heptahydrate / methanol / 0.17 h / 20 °C

2.2: 0.33 h / -78 °C

3.1: sodium hydride / tetrahydrofuran / 0.25 h / 20 °C

3.2: 3.5 h / 40 °C

4.1: hydrogenchloride; water / methanol / 3.5 h / Reflux

5.1: pyridine / -30 - 20 °C

6.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 0.33 h / -78 - 20 °C

6.2: 0.5 h / 50 °C

6.3: 3 h / 20 °C

With pyridine; hydrogenchloride; trifluoromethylsulfonic anhydride; cerium(III) chloride heptahydrate; water; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 1.3: Hofmann Degradation;

Reference yield:

(-)-(3aR,4S,6R,6aR)-4-(benzyloxy)-6-(tert-butoxymethyl)-2,2-dimethyl-5-methylenetetrahydro-3aH-cyclopenta[d][1,3]dioxole (1307273-59-1) → (-)-(6aR,8S,9R,9aR)-8-(benzyloxy)-2,2,4,4-tetraisopropyl-7-methyleneperhydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-ol (1307273-62-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride; water / methanol / 3.5 h / Reflux

2.1: pyridine / -30 - 20 °C

3.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 0.33 h / -78 - 20 °C

3.2: 0.5 h / 50 °C

3.3: 3 h / 20 °C

With pyridine; hydrogenchloride; trifluoromethylsulfonic anhydride; water; In methanol; dichloromethane;

upstream raw materials:

(3aR,6R,6aR)-6-(tert-butoxymethyl)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-one

(3aS,4S,6R,6aR)-6-(tert-butoxymethyl)-2,2-dimethyl-5-methylenetetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-ol

(-)-(3aR,4S,6R,6aR)-4-(benzyloxy)-6-(tert-butoxymethyl)-2,2-dimethyl-5-methylenetetrahydro-3aH-cyclopenta[d][1,3]dioxole

(-)-(1R,2R,3S,5R)-3-(benzyloxy)-5-(hydroxymethyl)-4-methylenecyclopentane-1,2-diol

Downstream raw materials:

(-)-(6aR,8S,9R,9aR)-8-(benzyloxy)-9-fluoro-2,2,4,4-tetraisopropyl-7-methylenehexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocine

C₁₄H₁₇FO₃

(-)-[(1R,2R,3S,4S)-2-(benzoyloxy)-4-(benzyloxy)-3-fluoro-5-methylenecyclopentyl]methyl benzoate

(-)-[(1R,2R,3R,4S)-2-(benzoyloxy)-3-fluoro-4-hydroxy-5-methylenecyclopentyl]methyl benzoate