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

Base Information

Chemical Name:(3E)-4-[(2'R,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]but-3-en-2-one
CAS No.:959792-05-3
Molecular Formula:C₄₇H₅₁NO₆Si
Molecular Weight:754.011
Hs Code.:

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

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

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

There total 3 articles about (3E)-4-[(2'R,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(tert-butyldiphenylsilyloxymethyl)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:

: C₄₄H₄₇NO₆Si

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

: 959792-05-3
(3E)-4-[(2'R,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]but-3-en-2-one

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

C₄₄H₄₇NO₆Si; In tetrahydrofuran; at 20 ℃; Further stages.;
DOI:10.1016/j.tetasy.2007.09.014

Reference yield:

: 959792-03-1
(2R,3S,4R,5R)-3,4-dibenzyloxy-N-benzoylcarbonyl-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine

: 959792-05-3
(3E)-4-[(2'R,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]but-3-en-2-one

Guidance literature:: Multi-step reaction with 2 steps

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

2.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C

2.2: 510 mg / tetrahydrofuran / 20 °C

With tetrapropylammonium perruthennate; 4 A molecular sieve; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; 2.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tetasy.2007.09.014

Reference yield:

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

: 959792-05-3
(3E)-4-[(2'R,3'R,4'S,5'R)-3',4'-dibenzyloxy-N-benzoylcarbonyl-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]but-3-en-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 67 percent / potassium carbonate / acetone / 2 h / 20 °C

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

3.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C

3.2: 510 mg / tetrahydrofuran / 20 °C

With tetrapropylammonium perruthennate; 4 A molecular sieve; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; acetone; 3.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tetasy.2007.09.014