(3aR,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl methanesulfonate

Base Information

• Chemical Name: (3aR,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl methanesulfonate
• CAS No.: 805245-43-6
• Molecular Formula: C₂₉H₂₉FO₆S
• Molecular Weight: 524.61
• Mol file: 805245-43-6.mol

Synonyms:(3aR,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl methanesulfonate

Chemical Property of (3aR,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl methanesulfonate

There total 14 articles about (3aR,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl methanesulfonate 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%

methanesulfonyl chloride (124-63-0) + (3aS,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (805245-42-5) → (3aR,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl methanesulfonate (805245-43-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/j.bmcl.2004.08.047 DOI:10.1081/NCN-200060286

Reference yield:

(3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one (805245-38-9) → (3aR,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl methanesulfonate (805245-43-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / NaBH₄; CeCl₃ / methanol / 0.5 h / 0 °C

2: 95 percent / imidazole / dimethylformamide / 40 °C

3: 51 percent / N-fluorobenzenesulfonimide; n-BuLi / tetrahydrofuran / 1 h / -78 °C

4: 98 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 20 °C

5: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; tetrabutyl ammonium fluoride; N-fluorobis(benzenesulfon)imide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/NCN-200060286

Reference yield:

(3aS,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (805245-39-0) → (3aR,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl methanesulfonate (805245-43-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / imidazole / dimethylformamide / 40 °C

2: 51 percent / N-fluorobenzenesulfonimide; n-BuLi / tetrahydrofuran / 1 h / -78 °C

3: 98 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 20 °C

4: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; N-fluorobis(benzenesulfon)imide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/NCN-200060286

upstream raw materials:

methanesulfonyl chloride

(3aS,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

(3aR,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one

(3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

Downstream raw materials:

(1S,4R,5S)-1-(6-aminopurine-9-yl)-2-fluoro-4,5-(O-isopropylidenedioxy)-3-(trityloxymethyl)-2-cyclopentene

((3aS,4S,6aR)-4-(6-amino-9H-purin-9-yl)-5-fluoro-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-6-yl)methanol

RX-3117