(1R,2R,3S,7aR)-3-benzoyloxymethyl-1,2-dibenzyloxypyrrolizidine

Base Information

• Chemical Name: (1R,2R,3S,7aR)-3-benzoyloxymethyl-1,2-dibenzyloxypyrrolizidine
• CAS No.: 713122-90-8
• Molecular Formula: C₂₉H₃₁NO₄
• Molecular Weight: 457.569
• Mol file: 713122-90-8.mol

Synonyms:(1R,2R,3S,7aR)-3-benzoyloxymethyl-1,2-dibenzyloxypyrrolizidine

Chemical Property of (1R,2R,3S,7aR)-3-benzoyloxymethyl-1,2-dibenzyloxypyrrolizidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,7aR)-3-benzoyloxymethyl-1,2-dibenzyloxypyrrolizidine

There total 5 articles about (1R,2R,3S,7aR)-3-benzoyloxymethyl-1,2-dibenzyloxypyrrolizidine 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: 55.0%

3-[(2'R,3'R,4'R,5'S)-5'-benzoyloxymethyl-3',4'-dibenzyloxy-N-benzyloxycarbonylpyrrolidin-2'-yl]prop-2-enal (713122-87-3) → (1R,2R,3S,7aR)-3-benzoyloxymethyl-1,2-dibenzyloxypyrrolizidine (713122-90-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 14h; under 3102.89 Torr;

DOI:10.1016/j.tetasy.2004.03.013

Reference yield:

(2R,3R,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (340970-04-9) → (1R,2R,3S,7aR)-3-benzoyloxymethyl-1,2-dibenzyloxypyrrolizidine (713122-90-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

2: 100 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 20 °C

3: N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

4: 1.13 g / toluene / 3 h / 60 °C

5: 55 percent / H₂ / Pd/C / methanol / 14 h / 3102.89 Torr

With dmap; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene; 4: Wittig reaction;

DOI:10.1016/j.tetasy.2004.03.013

Reference yield:

(2S,3R,4R,5R)-2'-O-benzoyl-3,4-dibenzyloxy-N-benzyloxycarbonyl-2,5-bis(hydroxymethyl)pyrrolidine (713122-84-0) → (1R,2R,3S,7aR)-3-benzoyloxymethyl-1,2-dibenzyloxypyrrolizidine (713122-90-8)

Guidance literature:

Multi-step reaction with 3 steps

1: N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

2: 1.13 g / toluene / 3 h / 60 °C

3: 55 percent / H₂ / Pd/C / methanol / 14 h / 3102.89 Torr

With tetrapropylammonium perruthennate; hydrogen; 4-methylmorpholine N-oxide; palladium on activated charcoal; In methanol; dichloromethane; toluene; 2: Wittig reaction;

DOI:10.1016/j.tetasy.2004.03.013

upstream raw materials:

3-[(2'R,3'R,4'R,5'S)-5'-benzoyloxymethyl-3',4'-dibenzyloxy-N-benzyloxycarbonylpyrrolidin-2'-yl]prop-2-enal

(2R,3R,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

(2S,3R,4R,5S)-2-Benzoyloxymethyl-3,4-bis-benzyloxy-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester

(2S,3R,4R,5R)-2'-O-benzoyl-3,4-dibenzyloxy-N-benzyloxycarbonyl-2,5-bis(hydroxymethyl)pyrrolidine

Downstream raw materials:

((1R,2R,3S,7aR)-1,2-Bis-benzyloxy-hexahydro-pyrrolizin-3-yl)-methanol