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

Base Information

• Chemical Name: (-)-(6aR,8S,9R,9aR)-8-(benzyloxy)-9-fluoro-2,2,4,4-tetraisopropyl-7-methylenehexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocine
• CAS No.: 1307273-63-7
• Molecular Formula: C₂₆H₄₃FO₄Si₂
• Molecular Weight: 494.794
• Mol file: 1307273-63-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (-)-(6aR,8S,9R,9aR)-8-(benzyloxy)-9-fluoro-2,2,4,4-tetraisopropyl-7-methylenehexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocine 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: 47.0%

(-)-(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)-9-fluoro-2,2,4,4-tetraisopropyl-7-methylenehexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocine (1307273-63-7)

Guidance literature:

With dimethylaminosulphur trifluoride; In dichloromethane; at 20 ℃; for 0.333333h;

DOI:10.1016/j.bmcl.2011.08.113

Reference yield:

(-)-(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) → (-)-(6aR,8S,9R,9aR)-8-(benzyloxy)-9-fluoro-2,2,4,4-tetraisopropyl-7-methylenehexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocine (1307273-63-7)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at 20 ℃; for 0.333333h;

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)-9-fluoro-2,2,4,4-tetraisopropyl-7-methylenehexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocine (1307273-63-7)

Guidance literature:

Multi-step reaction with 4 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

4.1: diethylamino-sulfur trifluoride / dichloromethane / 0.33 h / 20 °C

With pyridine; hydrogenchloride; trifluoromethylsulfonic anhydride; diethylamino-sulfur trifluoride; water; In methanol; dichloromethane;

upstream raw materials:

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

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

(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

Downstream raw materials:

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

(+)-9-[(1R,2R,3R,4R)-2-fluoro-3-benzyloxy-4-(benzyloxymethyl)-5-methylenecyclopentan-1-yl]-6-N,N-di-Boc-adenine