(1S,2R,3R,5S,7aS)-3'-benzoyloxymethyl-1,2-dibenzyloxy-5-methylpyrrolizidine

Base Information

• Chemical Name: (1S,2R,3R,5S,7aS)-3'-benzoyloxymethyl-1,2-dibenzyloxy-5-methylpyrrolizidine
• CAS No.: 900780-96-3
• Molecular Formula: C₃₀H₃₃NO₄
• Molecular Weight: 471.596
• Mol file: 900780-96-3.mol

Synonyms:(1S,2R,3R,5S,7aS)-3'-benzoyloxymethyl-1,2-dibenzyloxy-5-methylpyrrolizidine

Chemical Property of (1S,2R,3R,5S,7aS)-3'-benzoyloxymethyl-1,2-dibenzyloxy-5-methylpyrrolizidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3R,5S,7aS)-3'-benzoyloxymethyl-1,2-dibenzyloxy-5-methylpyrrolizidine

There total 7 articles about (1S,2R,3R,5S,7aS)-3'-benzoyloxymethyl-1,2-dibenzyloxy-5-methylpyrrolizidine 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: 74.0%

4-[(2'S,3'S,4'R,5'R)-5'-benzoyloxymethyl-3',4'-dibenzyloxy-N-benzyloxycarbonylpyrrolidin-2'-yl]but-3-en-2-one (900780-95-2) → (1S,2R,3R,5S,7aS)-3'-benzoyloxymethyl-1,2-dibenzyloxy-5-methylpyrrolizidine (900780-96-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 24h; under 3102.89 Torr;

DOI:10.1016/j.tet.2006.04.003

Reference yield:

(2S,3S,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (872345-55-6) → (1S,2R,3R,5S,7aS)-3'-benzoyloxymethyl-1,2-dibenzyloxy-5-methylpyrrolizidine (900780-96-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 79 percent / K₂CO₃ / acetone / 0.5 h / 20 °C

2.1: 95 percent / TEA; DMAP / CH₂Cl₂ / 20 h / 20 °C

3.1: 84 percent / TBAF*3H₂O / tetrahydrofuran / 20 °C

4.1: 4 Angstroem molecular sieves; NMO; TPAP / CH₂Cl₂ / 1 h / 20 °C

5.1: NaH / tetrahydrofuran / 1 h / 20 °C

5.2: 520 mg / tetrahydrofuran / 0.08 h / 20 °C

6.1: 74 percent / H₂ / Pd/C / methanol / 24 h / 3102.89 Torr

With dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; TEA; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone; 5.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2006.04.003

Reference yield:

(2R,3R,4S,5R)-2-Benzoyloxymethyl-3,4-bis-benzyloxy-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester (900780-94-1) → (1S,2R,3R,5S,7aS)-3'-benzoyloxymethyl-1,2-dibenzyloxy-5-methylpyrrolizidine (900780-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 520 mg / tetrahydrofuran / 0.08 h / 20 °C

2.1: 74 percent / H₂ / Pd/C / methanol / 24 h / 3102.89 Torr

With hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; 1.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2006.04.003

upstream raw materials:

4-[(2'S,3'S,4'R,5'R)-5'-benzoyloxymethyl-3',4'-dibenzyloxy-N-benzyloxycarbonylpyrrolidin-2'-yl]but-3-en-2-one

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

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

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

Downstream raw materials:

(1S,2R,3R,5S,7aS)-1,2-bis(benzyloxy)-3-(hydroxymethyl)-5-methylpyrrolizidine