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

Base Information

Chemical Name:4-[(2'S,3'S,4'R,5'R)-5'-benzoyloxymethyl-3',4'-dibenzyloxy-N-benzyloxycarbonylpyrrolidin-2'-yl]but-3-en-2-one
CAS No.:900780-95-2
Molecular Formula:C₃₈H₃₇NO₇
Molecular Weight:619.714
Hs Code.:

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

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

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

There total 6 articles about 4-[(2'S,3'S,4'R,5'R)-5'-benzoyloxymethyl-3',4'-dibenzyloxy-N-benzyloxycarbonylpyrrolidin-2'-yl]but-3-en-2-one 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:

: 900780-94-1
(2R,3R,4S,5R)-2-Benzoyloxymethyl-3,4-bis-benzyloxy-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester

: 1067-71-6
Diethyl (2-oxopropyl)phosphonate

: 900780-95-2
4-[(2'S,3'S,4'R,5'R)-5'-benzoyloxymethyl-3',4'-dibenzyloxy-N-benzyloxycarbonylpyrrolidin-2'-yl]but-3-en-2-one

Guidance literature:: Diethyl (2-oxopropyl)phosphonate; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;

(2R,3R,4S,5R)-2-Benzoyloxymethyl-3,4-bis-benzyloxy-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester; In tetrahydrofuran; at 20 ℃; for 0.0833333h;
DOI:10.1016/j.tet.2006.04.003

Reference yield:

: 872345-55-6
(2S,3S,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

: 900780-95-2
4-[(2'S,3'S,4'R,5'R)-5'-benzoyloxymethyl-3',4'-dibenzyloxy-N-benzyloxycarbonylpyrrolidin-2'-yl]but-3-en-2-one

Guidance literature:: Multi-step reaction with 5 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

With dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; TEA; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; In tetrahydrofuran; dichloromethane; acetone; 5.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2006.04.003

Reference yield:

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

: 900780-95-2
4-[(2'S,3'S,4'R,5'R)-5'-benzoyloxymethyl-3',4'-dibenzyloxy-N-benzyloxycarbonylpyrrolidin-2'-yl]but-3-en-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 4 Angstroem molecular sieves; NMO; TPAP / CH₂Cl₂ / 1 h / 20 °C

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

2.2: 520 mg / tetrahydrofuran / 0.08 h / 20 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; sodium hydride; In tetrahydrofuran; dichloromethane; 2.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2006.04.003