(3E)-4-[(2'S,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(pivaloyloxymethyl)pyrrolidin-2'-yl]but-3-en-2-one

Base Information

Chemical Name:(3E)-4-[(2'S,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(pivaloyloxymethyl)pyrrolidin-2'-yl]but-3-en-2-one
CAS No.:959792-16-6
Molecular Formula:C₃₆H₄₁NO₇
Molecular Weight:599.724
Hs Code.:

Synonyms:(3E)-4-[(2'S,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(pivaloyloxymethyl)pyrrolidin-2'-yl]but-3-en-2-one

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Chemical Property of (3E)-4-[(2'S,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(pivaloyloxymethyl)pyrrolidin-2'-yl]but-3-en-2-one

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Technology Process of (3E)-4-[(2'S,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(pivaloyloxymethyl)pyrrolidin-2'-yl]but-3-en-2-one

There total 3 articles about (3E)-4-[(2'S,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(pivaloyloxymethyl)pyrrolidin-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: 83.0%

: 959792-14-4
C₃₃H₃₇NO₇

: 1439-36-7
1-triphenylphosphoranylidene-2-propanone

: 959792-16-6
(3E)-4-[(2'S,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(pivaloyloxymethyl)pyrrolidin-2'-yl]but-3-en-2-one

Guidance literature:: In toluene; at 100 ℃; for 3h;
DOI:10.1016/j.tetasy.2007.09.014

Reference yield:

: 959792-12-2
(2R,3S,4R,5S)-3,4-dibenzyloxy-N-benzoylcarbonyl-2,5-bis(hydroxymethyl)-2'-O-pivaloylpyrrolidine

: 959792-16-6
(3E)-4-[(2'S,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(pivaloyloxymethyl)pyrrolidin-2'-yl]but-3-en-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C

2: 83 percent / toluene / 3 h / 100 °C

With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In dichloromethane; toluene; 2: Wittig reaction;
DOI:10.1016/j.tetasy.2007.09.014

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 959792-16-6
(3E)-4-[(2'S,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(pivaloyloxymethyl)pyrrolidin-2'-yl]but-3-en-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 68 percent / potassium carbonate / acetone / 12 h / 20 °C

2: N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C

3: 83 percent / toluene / 3 h / 100 °C

With tetrapropylammonium perruthennate; 4 A molecular sieve; potassium carbonate; 4-methylmorpholine N-oxide; In dichloromethane; acetone; toluene; 3: Wittig reaction;
DOI:10.1016/j.tetasy.2007.09.014