(1S,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-bicyclo[2.2.2]oct-5-en-2-one

Base Information

Chemical Name:(1S,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-bicyclo[2.2.2]oct-5-en-2-one
CAS No.:176659-54-4
Molecular Formula:C₂₅H₂₈O₃
Molecular Weight:376.496
Hs Code.:

Synonyms:(1S,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-bicyclo[2.2.2]oct-5-en-2-one

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Chemical Property of (1S,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-bicyclo[2.2.2]oct-5-en-2-one

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Technology Process of (1S,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-bicyclo[2.2.2]oct-5-en-2-one

There total 7 articles about (1S,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-bicyclo[2.2.2]oct-5-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: 88.0%

: 176659-53-3
Acetic acid (1R,2R,4S,7R,8S)-7,8-bis-benzyloxymethyl-1-methyl-3-oxo-bicyclo[2.2.2]oct-5-en-2-yl ester

: 176659-54-4
(1S,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-bicyclo[2.2.2]oct-5-en-2-one

Guidance literature:: With samarium diiodide; acetic acid; In tetrahydrofuran; at 18 ℃; for 0.333333h;
DOI:10.1039/cc9960000869

Reference yield:

: 114763-30-3
(3aR,7aS)-2,2,4-trimethyl-3a,7a-dihydro-1,3-benzodioxole

: 176659-54-4
(1S,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-bicyclo[2.2.2]oct-5-en-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 68 percent / CH₂Cl₂ / 24 h / 0 - 18 °C

2: 88 percent / LiAlH₄ / tetrahydrofuran / 3 h / 66 °C

3: 99 percent / NaH, Bu₄NI / dimethylformamide / 18 h / 0 - 18 °C

4: 100 percent / aq. AcOH / 16 h / 80 °C

5: 97 percent / 4-AcNH-TEMPO, p-TsOH / CH₂Cl₂ / 3 h / 18 °C

6: 92 percent / pyridine / CH₂Cl₂ / 18 h / 18 °C

7: 88 percent / SmI₂, AcOH / tetrahydrofuran / 0.33 h / 18 °C

With pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; lithium aluminium tetrahydride; samarium diiodide; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/cc9960000869

Reference yield:

: 176659-49-7
((1S,2S,6R,7R,8R,9S)-9-Hydroxymethyl-4,4,7-trimethyl-3,5-dioxa-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl)-methanol

: 176659-54-4
(1S,4R,7S,8R)-7,8-Bis-benzyloxymethyl-4-methyl-bicyclo[2.2.2]oct-5-en-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / NaH, Bu₄NI / dimethylformamide / 18 h / 0 - 18 °C

2: 100 percent / aq. AcOH / 16 h / 80 °C

3: 97 percent / 4-AcNH-TEMPO, p-TsOH / CH₂Cl₂ / 3 h / 18 °C

4: 92 percent / pyridine / CH₂Cl₂ / 18 h / 18 °C

5: 88 percent / SmI₂, AcOH / tetrahydrofuran / 0.33 h / 18 °C

With pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; samarium diiodide; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/cc9960000869