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

Base Information

Chemical Name:Acetic acid (1S,2S,4R,7S,8R)-7,8-bis-benzyloxymethyl-4-methyl-3-oxo-bicyclo[2.2.2]oct-5-en-2-yl ester
CAS No.:176659-60-2
Molecular Formula:C₂₇H₃₀O₅
Molecular Weight:434.532
Hs Code.:

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

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

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

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

: 108-24-7
acetic anhydride

: 176659-59-9
(1R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-3-hydroxy-1-methyl-bicyclo[2.2.2]oct-5-en-2-one

: 176659-60-2
Acetic acid (1S,2S,4R,7S,8R)-7,8-bis-benzyloxymethyl-4-methyl-3-oxo-bicyclo[2.2.2]oct-5-en-2-yl ester

Guidance literature:: With pyridine; In dichloromethane; at 18 ℃; for 18h;
DOI:10.1039/cc9960000869

Reference yield:

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

: 176659-60-2
Acetic acid (1S,2S,4R,7S,8R)-7,8-bis-benzyloxymethyl-4-methyl-3-oxo-bicyclo[2.2.2]oct-5-en-2-yl ester

Guidance literature:: Multi-step reaction with 8 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: 68 percent / imidazole / dimethylformamide / 24 h / 18 °C

6: Me₂SO, TFAA / CH₂Cl₂ / 1 h / -60 °C

7: TBAF / tetrahydrofuran; CH₂Cl₂ / 18 h / 18 °C

8: pyridine / CH₂Cl₂ / 18 h / 18 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; dimethyl sulfoxide; trifluoroacetic anhydride; 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

: 176659-60-2
Acetic acid (1S,2S,4R,7S,8R)-7,8-bis-benzyloxymethyl-4-methyl-3-oxo-bicyclo[2.2.2]oct-5-en-2-yl ester

Guidance literature:: Multi-step reaction with 6 steps

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

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

3: 68 percent / imidazole / dimethylformamide / 24 h / 18 °C

4: Me₂SO, TFAA / CH₂Cl₂ / 1 h / -60 °C

5: TBAF / tetrahydrofuran; CH₂Cl₂ / 18 h / 18 °C

6: pyridine / CH₂Cl₂ / 18 h / 18 °C

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; dimethyl sulfoxide; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/cc9960000869