(3R,4R)-3,4-Bis-benzyloxy-1-((Z)-4-trimethylsilanyl-but-3-enyl)-pyrrolidine-2,5-dione

Base Information

Chemical Name:(3R,4R)-3,4-Bis-benzyloxy-1-((Z)-4-trimethylsilanyl-but-3-enyl)-pyrrolidine-2,5-dione
CAS No.:173289-46-8
Molecular Formula:C₂₅H₃₁NO₄Si
Molecular Weight:437.611
Hs Code.:

Synonyms:(3R,4R)-3,4-Bis-benzyloxy-1-((Z)-4-trimethylsilanyl-but-3-enyl)-pyrrolidine-2,5-dione

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Chemical Property of (3R,4R)-3,4-Bis-benzyloxy-1-((Z)-4-trimethylsilanyl-but-3-enyl)-pyrrolidine-2,5-dione

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Technology Process of (3R,4R)-3,4-Bis-benzyloxy-1-((Z)-4-trimethylsilanyl-but-3-enyl)-pyrrolidine-2,5-dione

There total 1 articles about (3R,4R)-3,4-Bis-benzyloxy-1-((Z)-4-trimethylsilanyl-but-3-enyl)-pyrrolidine-2,5-dione 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: 77.0%

: 127299-55-2
(3R,4R)-3,4-bis(benzyloxy)pyrrolidine-2,5-dione

: 87682-77-7
(Z)-4-(trimethylsilyl)-but-3-en-1-ol

: 173289-46-8
(3R,4R)-3,4-Bis-benzyloxy-1-((Z)-4-trimethylsilanyl-but-3-enyl)-pyrrolidine-2,5-dione

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; Ambient temperature;
DOI:10.1021/ja9529910

Reference yield: 98.0%

: 173289-46-8
(3R,4R)-3,4-Bis-benzyloxy-1-((Z)-4-trimethylsilanyl-but-3-enyl)-pyrrolidine-2,5-dione

: (3R,4R)-3,4-Bis-benzyloxy-5-hydroxy-1-((Z)-4-trimethylsilanyl-but-3-enyl)-pyrrolidin-2-one

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;
DOI:10.1021/ja9529910

Reference yield:

: 173289-46-8
(3R,4R)-3,4-Bis-benzyloxy-1-((Z)-4-trimethylsilanyl-but-3-enyl)-pyrrolidine-2,5-dione

: 173396-42-4
(4aS,6S,7S,7aS)-6,7-Bis-benzyloxy-5-eth-(Z)-ylidene-2,4a,5,6,7,7a-hexahydro-[1]pyrindine-1-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / NaBH₄ / methanol / 0.5 h / 0 °C

2: 95 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 99 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) LiAlHBu(i-Bu)2, 2.) aq. NaOH / 1.) THF, hexane, RT, 10 min, 2.) THF, hexane, CH₂Cl₂, RT, 1 h

5: 88 percent / Ph₃P / CH₂Cl₂ / 0.25 h / Ambient temperature

6: 1.) BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 2 h, b) RT, overnight

7: Pd(OAc)2(PPh₃)2, AcOH / benzene / 4 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; bis(triphenylphosphine) palladium (Il) acetate; lithium n-butyldiisobutylaluminum hydride; boron trifluoride diethyl etherate; acetic acid; triethylamine; triphenylphosphine; In methanol; dichloromethane; benzene;
DOI:10.1021/ja9529910