Acetic acid (R)-2-{(4S,5R)-2,2-dimethyl-5-[(S)-3-oxo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-2-yl]-[1,3]dioxolan-4-yl}-2-trifluoromethanesulfonyloxy-ethyl ester

Base Information

• Chemical Name: Acetic acid (R)-2-{(4S,5R)-2,2-dimethyl-5-[(S)-3-oxo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-2-yl]-[1,3]dioxolan-4-yl}-2-trifluoromethanesulfonyloxy-ethyl ester
• CAS No.: 133495-06-4
• Molecular Formula: C₃₃H₃₂F₃NO₈S
• Molecular Weight: 659.68

Synonyms:

Chemical Property of Acetic acid (R)-2-{(4S,5R)-2,2-dimethyl-5-[(S)-3-oxo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-2-yl]-[1,3]dioxolan-4-yl}-2-trifluoromethanesulfonyloxy-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (R)-2-{(4S,5R)-2,2-dimethyl-5-[(S)-3-oxo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-2-yl]-[1,3]dioxolan-4-yl}-2-trifluoromethanesulfonyloxy-ethyl ester

There total 11 articles about Acetic acid (R)-2-{(4S,5R)-2,2-dimethyl-5-[(S)-3-oxo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-2-yl]-[1,3]dioxolan-4-yl}-2-trifluoromethanesulfonyloxy-ethyl ester 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:

methyl 2-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate (117462-55-2) → Acetic acid (R)-2-{(4S,5R)-2,2-dimethyl-5-[(S)-3-oxo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-2-yl]-[1,3]dioxolan-4-yl}-2-trifluoromethanesulfonyloxy-ethyl ester (133495-06-4)

Guidance literature:

Multi-step reaction with 10 steps

1: H₂ / 10percent Pd/C / ethyl acetate / 24 h / 760 Torr

2: Pb(NO₃)2, Et₃N / CH₂Cl₂ / 48 h / Ambient temperature

3: 94 percent / DIBAL / toluene / 0.5 h / -78 °C

4: 1) N-chlorosuccinimide, Me₂S, 2) NEt₃ / 1) toluene, -25 deg C, 5.5 h, 2) 20 min.

5: 91 percent / tetrahydrofuran / 1 h / -40 deg C to r.t.

6: 1) N-chlorosuccinimide, Me₂S, 2) NEt₃ / 1) toluene, -25 deg C, 5.5 h 2) 20 min

7: HBr, H₂O / diethyl ether / 0.5 h / 0 °C

8: NaHCO₃, Na₂CO₃ / H₂O / 2.5 h / Ambient temperature

9: 80 percent / pyridine / 20 h / 0 °C

10: pyridine / CH₂Cl₂ / 0.33 h / -15 °C

With pyridine; N-chloro-succinimide; lead(II) nitrate; dimethylsulfide; water; hydrogen bromide; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/jo00011a047

Reference yield:

trifluoromethylsulfonic anhydride (358-23-6) + 2-(1',2'-O-isopropylidene-1',2',3'-trihydroxy-4'-acetoxybutyl)-3-oxo-N-(9-phenylfluoren-9-yl)pyrrolidine (133473-20-8) → Acetic acid (R)-2-{(4S,5R)-2,2-dimethyl-5-[(S)-3-oxo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-2-yl]-[1,3]dioxolan-4-yl}-2-trifluoromethanesulfonyloxy-ethyl ester (133495-06-4)

Guidance literature:

With pyridine; In dichloromethane; at -15 ℃; for 0.333333h;

DOI:10.1021/jo00011a047

Reference yield:

9-bromo-9-phenyl-9H-fluorene (55135-66-5) → Acetic acid (R)-2-{(4S,5R)-2,2-dimethyl-5-[(S)-3-oxo-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-2-yl]-[1,3]dioxolan-4-yl}-2-trifluoromethanesulfonyloxy-ethyl ester (133495-06-4)

Guidance literature:

Multi-step reaction with 9 steps

1: Pb(NO₃)2, Et₃N / CH₂Cl₂ / 48 h / Ambient temperature

2: 94 percent / DIBAL / toluene / 0.5 h / -78 °C

3: 1) N-chlorosuccinimide, Me₂S, 2) NEt₃ / 1) toluene, -25 deg C, 5.5 h, 2) 20 min.

4: 91 percent / tetrahydrofuran / 1 h / -40 deg C to r.t.

5: 1) N-chlorosuccinimide, Me₂S, 2) NEt₃ / 1) toluene, -25 deg C, 5.5 h 2) 20 min

6: HBr, H₂O / diethyl ether / 0.5 h / 0 °C

7: NaHCO₃, Na₂CO₃ / H₂O / 2.5 h / Ambient temperature

8: 80 percent / pyridine / 20 h / 0 °C

9: pyridine / CH₂Cl₂ / 0.33 h / -15 °C

With pyridine; N-chloro-succinimide; lead(II) nitrate; dimethylsulfide; water; hydrogen bromide; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;

DOI:10.1021/jo00011a047

upstream raw materials:

trifluoromethylsulfonic anhydride

2-(1',2'-O-isopropylidene-1',2',3'-trihydroxy-4'-acetoxybutyl)-3-oxo-N-(9-phenylfluoren-9-yl)pyrrolidine

9-bromo-9-phenyl-9H-fluorene

methyl 3,4;5,6-di-O-isopropylidene-2-amino-2-deoxy-D-mannate

Downstream raw materials:

2-(1',2'-O-isopropylidene-1',2'-dihydroxy-3',4'-diacetoxybutyl)-3-oxo-N-(9-phenylfluoren-9-yl)pyrrolidine

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine

2-(1',2'-O-isopropylidene-1',2',3',4'-tetrahydroxybutyl)-3-hydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine

2-(1',2'-O-isopropylidene-1',2'-dihydroxy-3',4'-diacetoxybutyl)-3-hydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine

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