(R,E)-dimethyl 3-((R)-4-(benzyloxy)-3-methylbutylidene)-1,4-dimethyl-5-oxopyrrolidine-2,2-dicarboxylate

Base Information

Chemical Name:(R,E)-dimethyl 3-((R)-4-(benzyloxy)-3-methylbutylidene)-1,4-dimethyl-5-oxopyrrolidine-2,2-dicarboxylate
CAS No.:955959-41-8
Molecular Formula:C₂₂H₂₉NO₆
Molecular Weight:403.475
Hs Code.:

Synonyms:(R,E)-dimethyl 3-((R)-4-(benzyloxy)-3-methylbutylidene)-1,4-dimethyl-5-oxopyrrolidine-2,2-dicarboxylate

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Chemical Property of (R,E)-dimethyl 3-((R)-4-(benzyloxy)-3-methylbutylidene)-1,4-dimethyl-5-oxopyrrolidine-2,2-dicarboxylate

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Technology Process of (R,E)-dimethyl 3-((R)-4-(benzyloxy)-3-methylbutylidene)-1,4-dimethyl-5-oxopyrrolidine-2,2-dicarboxylate

There total 5 articles about (R,E)-dimethyl 3-((R)-4-(benzyloxy)-3-methylbutylidene)-1,4-dimethyl-5-oxopyrrolidine-2,2-dicarboxylate 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: 91.0%

: 1332721-77-3
dimethyl 2-((2R,6R)-7-(benzyloxy)-N,2,6-trimethylhept-3-ynamido)malonate

: 955959-41-8
(R,E)-dimethyl 3-((R)-4-(benzyloxy)-3-methylbutylidene)-1,4-dimethyl-5-oxopyrrolidine-2,2-dicarboxylate

Guidance literature:: With indium(III) triflate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 6h; stereoselective reaction; Inert atmosphere; Reflux;
DOI:10.1021/ol202306d

Reference yield: 84.0%

: 955959-42-9
dimethyl 2-((E,2S,6R)-7-(benzyloxy)-3-iodo-2,6-dimethylhept-3-enoylmethylamino)malonate

: 955959-41-8
(R,E)-dimethyl 3-((R)-4-(benzyloxy)-3-methylbutylidene)-1,4-dimethyl-5-oxopyrrolidine-2,2-dicarboxylate

Guidance literature:: With tetrabutylammomium bromide; potassium carbonate; triphenylphosphine; palladium diacetate; In water; N,N-dimethyl-formamide; at 70 ℃; for 1.5h;
DOI:10.1002/anie.200702229

Reference yield:

: 955959-44-1
((2R,6R)-7-benzyloxy)-2,6-dimethylhept-3-yn-1-ol

: 955959-41-8
(R,E)-dimethyl 3-((R)-4-(benzyloxy)-3-methylbutylidene)-1,4-dimethyl-5-oxopyrrolidine-2,2-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: Jones reagent / acetone / 4 h / 0 °C / Inert atmosphere

2: thionyl chloride / toluene / 10 h / 0 - 20 °C / Inert atmosphere

3: toluene / 2 h / 0 - 20 °C / Inert atmosphere

4: indium(III) triflate; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / Inert atmosphere; Reflux

With indium(III) triflate; Jones reagent; thionyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; toluene; 1: Jones oxidation;
DOI:10.1021/ol202306d