(3S,4S)-5-(Z)-benzylidene-3-hydroxy-3-propionyl-4-trimethylsilanyloxy-pyrrolidin-2-one

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Chemical Name:(3S,4S)-5-(Z)-benzylidene-3-hydroxy-3-propionyl-4-trimethylsilanyloxy-pyrrolidin-2-one
CAS No.:859216-40-3
Molecular Formula:C₁₇H₂₃NO₄Si
Molecular Weight:333.459
Hs Code.:

Synonyms:(3S,4S)-5-(Z)-benzylidene-3-hydroxy-3-propionyl-4-trimethylsilanyloxy-pyrrolidin-2-one

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Chemical Property of (3S,4S)-5-(Z)-benzylidene-3-hydroxy-3-propionyl-4-trimethylsilanyloxy-pyrrolidin-2-one

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Technology Process of (3S,4S)-5-(Z)-benzylidene-3-hydroxy-3-propionyl-4-trimethylsilanyloxy-pyrrolidin-2-one

There total 1 articles about (3S,4S)-5-(Z)-benzylidene-3-hydroxy-3-propionyl-4-trimethylsilanyloxy-pyrrolidin-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:

: 474915-86-1
(3S,4S)-5-(Z)-benzylidene-3-hydroxy-3-propionyl-4-triisopropylsiloxypyrrolidin-2-one

: 859216-40-3
(3S,4S)-5-(Z)-benzylidene-3-hydroxy-3-propionyl-4-trimethylsilanyloxy-pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / TBAF / tetrahydrofuran / 72 h / -30 °C

2: 83 percent / imidazole / dimethylformamide / 0.08 h / -78 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo050664x

Reference yield: 32.0%

: 859216-17-4
(2S,3R)-(Z)-2,3-epoxy-hept-4-enal

: 859216-40-3
(3S,4S)-5-(Z)-benzylidene-3-hydroxy-3-propionyl-4-trimethylsilanyloxy-pyrrolidin-2-one

: 859216-42-5
(3S,4S)-5-(Z)-benzylidene-3-((4R,5R)-(Z)-4,5-epoxy-3-hydroxy-2-methylnon-6-enoyl)-hydroxy-4-trimethylsilanyloxy-pyrrolidin-2-one

Guidance literature:: (3S,4S)-5-(Z)-benzylidene-3-hydroxy-3-propionyl-4-trimethylsilanyloxy-pyrrolidin-2-one; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(2S,3R)-(Z)-2,3-epoxy-hept-4-enal; In tetrahydrofuran; hexane; at -78 - -50 ℃; for 1h;
DOI:10.1021/jo050664x

Reference yield:

: 859216-40-3
(3S,4S)-5-(Z)-benzylidene-3-hydroxy-3-propionyl-4-trimethylsilanyloxy-pyrrolidin-2-one

: (5S,8R,9R)-2-[(2S,3R)-((Z)-3-But-1-enyl)-oxiranyl]-8-hydroxy-8-(hydroxy-phenyl-methyl)-3-methyl-9-trimethylsilanyloxy-1-oxa-7-aza-spiro[4.4]non-2-ene-4,6-dione

Guidance literature:: Multi-step reaction with 3 steps

1.1: LDA; HMPA / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 32 percent / tetrahydrofuran; hexane / 1 h / -78 - -50 °C

2.1: 52 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.05 h / 20 °C

3.1: 10 percent / molecular sieves 3 Angstroem; dimethyl dioxirane / acetone / 4 h / -60 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; 3 A molecular sieve; 3,3-dimethyldioxirane; sodium hydrogencarbonate; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; acetone;
DOI:10.1021/jo050664x