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

Base Information

• Chemical Name: (2R,3R,4S,5S)-2'-O-benzoyl-3,4-dibenzyloxy-N-benzyloxycarbonyl-2,5-bis(hydroxymethyl)pyrrolidine
• CAS No.: 900780-93-0
• Molecular Formula: C₃₅H₃₅NO₇
• Molecular Weight: 581.665
• Mol file: 900780-93-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (2R,3R,4S,5S)-2'-O-benzoyl-3,4-dibenzyloxy-N-benzyloxycarbonyl-2,5-bis(hydroxymethyl)pyrrolidine 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: 84.0%

(2R,3R,4S,5S)-2'-O-benzoyl-3,4-dibenzyloxy-N-benzyloxycarbonyl-5'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (900780-92-9) → (2R,3R,4S,5S)-2'-O-benzoyl-3,4-dibenzyloxy-N-benzyloxycarbonyl-2,5-bis(hydroxymethyl)pyrrolidine (900780-93-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

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) → (2R,3R,4S,5S)-2'-O-benzoyl-3,4-dibenzyloxy-N-benzyloxycarbonyl-2,5-bis(hydroxymethyl)pyrrolidine (900780-93-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / K₂CO₃ / acetone / 0.5 h / 20 °C

2: 95 percent / TEA; DMAP / CH₂Cl₂ / 20 h / 20 °C

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

With dmap; TEA; tetrabutyl ammonium fluoride; potassium carbonate; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1016/j.tet.2006.04.003

Reference yield:

(2S,3S,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (900780-88-3) → (2R,3R,4S,5S)-2'-O-benzoyl-3,4-dibenzyloxy-N-benzyloxycarbonyl-2,5-bis(hydroxymethyl)pyrrolidine (900780-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / TEA; DMAP / CH₂Cl₂ / 20 h / 20 °C

2: 84 percent / TBAF*3H₂O / tetrahydrofuran / 20 °C

With dmap; TEA; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2006.04.003

upstream raw materials:

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

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

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

benzyl chloroformate

Downstream 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

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

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