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

Base Information

Chemical Name:(1R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-3-hydroxy-1-methyl-bicyclo[2.2.2]oct-5-en-2-one
CAS No.:176659-59-9
Molecular Formula:C₂₅H₂₈O₄
Molecular Weight:392.495
Hs Code.:

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

Suppliers and Price of (1R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-3-hydroxy-1-methyl-bicyclo[2.2.2]oct-5-en-2-one

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (1R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-3-hydroxy-1-methyl-bicyclo[2.2.2]oct-5-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (1R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-3-hydroxy-1-methyl-bicyclo[2.2.2]oct-5-en-2-one

There total 7 articles about (1R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-3-hydroxy-1-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:

: 176659-58-8
(1R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-bicyclo[2.2.2]oct-5-en-2-one

: 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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; at 18 ℃; for 18h; Yield given;
DOI:10.1039/cc9960000869

Reference yield:

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

: 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

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

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

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

With 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

: 176659-59-9
(1R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-3-hydroxy-1-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: 68 percent / imidazole / dimethylformamide / 24 h / 18 °C

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

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

With 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