2,2-Dimethyl-propionic acid (1S,2S,5S,6R)-5-(tert-butyl-diphenyl-silanyloxy)-3-[1-methoxy-meth-(E)-ylidene]-7,7-dimethyl-bicyclo[4.1.0]hept-2-ylmethyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (1S,2S,5S,6R)-5-(tert-butyl-diphenyl-silanyloxy)-3-[1-methoxy-meth-(E)-ylidene]-7,7-dimethyl-bicyclo[4.1.0]hept-2-ylmethyl ester
CAS No.:267872-86-6
Molecular Formula:C₃₃H₄₆O₄Si
Molecular Weight:534.811
Hs Code.:

2,2-Dimethyl-propionic acid (1S,2S,5S,6R)-5-(tert-butyl-diphenyl-silanyloxy)-3-[1-methoxy-meth-(E)-ylidene]-7,7-dimethyl-bicyclo[4.1.0]hept-2-ylmethyl ester

Synonyms:2,2-Dimethyl-propionic acid (1S,2S,5S,6R)-5-(tert-butyl-diphenyl-silanyloxy)-3-[1-methoxy-meth-(E)-ylidene]-7,7-dimethyl-bicyclo[4.1.0]hept-2-ylmethyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (1S,2S,5S,6R)-5-(tert-butyl-diphenyl-silanyloxy)-3-[1-methoxy-meth-(E)-ylidene]-7,7-dimethyl-bicyclo[4.1.0]hept-2-ylmethyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (1S,2S,5S,6R)-5-(tert-butyl-diphenyl-silanyloxy)-3-[1-methoxy-meth-(E)-ylidene]-7,7-dimethyl-bicyclo[4.1.0]hept-2-ylmethyl ester

There total 11 articles about 2,2-Dimethyl-propionic acid (1S,2S,5S,6R)-5-(tert-butyl-diphenyl-silanyloxy)-3-[1-methoxy-meth-(E)-ylidene]-7,7-dimethyl-bicyclo[4.1.0]hept-2-ylmethyl 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: 73.0%

: 267872-85-5
2,2-Dimethyl-propionic acid (1R,2R,5S,6R)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-3-(methoxy-trimethylsilanyl-methyl)-7,7-dimethyl-bicyclo[4.1.0]hept-2-ylmethyl ester

: 267872-86-6
2,2-Dimethyl-propionic acid (1S,2S,5S,6R)-5-(tert-butyl-diphenyl-silanyloxy)-3-[1-methoxy-meth-(E)-ylidene]-7,7-dimethyl-bicyclo[4.1.0]hept-2-ylmethyl ester

Guidance literature:: With potassium hydride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1016/S0040-4039(99)02103-6

Reference yield:

: 267872-80-0
(1R,2R,6R)-2-Hydroxymethyl-7,7-dimethyl-bicyclo[4.1.0]hept-4-en-3-one

: 267872-86-6
2,2-Dimethyl-propionic acid (1S,2S,5S,6R)-5-(tert-butyl-diphenyl-silanyloxy)-3-[1-methoxy-meth-(E)-ylidene]-7,7-dimethyl-bicyclo[4.1.0]hept-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: aq. H₂O₂; NaOH / tetrahydrofuran / 2 h / 0 °C

2: pyridine / CH₂Cl₂ / 10 h / 20 °C

3: 87 percent / Al-Hg / tetrahydrofuran; aq. ethanol / 96 h / -45 °C

4: 60 percent / imidazole / dimethylformamide / 6 h / 20 °C

5: 70 percent / s-BuLi; CeCl₃ / tetrahydrofuran / 2 h / -40 - 0 °C

6: 73 percent / KH / tetrahydrofuran / 2 h / 20 °C

With pyridine; 1H-imidazole; sodium hydroxide; cerium(III) chloride; aluminium amalgam; dihydrogen peroxide; sec.-butyllithium; potassium hydride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Epoxidation / 2: Esterification / 3: Reduction / 4: silylation / 5: Alkylation / 6: Hydrolysis;
DOI:10.1016/S0040-4039(99)02103-6

Reference yield:

: 267872-79-7
(1R,2R,6R)-2-Hydroxymethyl-7,7-dimethyl-bicyclo[4.1.0]heptan-3-one

: 267872-86-6
2,2-Dimethyl-propionic acid (1S,2S,5S,6R)-5-(tert-butyl-diphenyl-silanyloxy)-3-[1-methoxy-meth-(E)-ylidene]-7,7-dimethyl-bicyclo[4.1.0]hept-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 83 percent / imidazole / dimethylformamide / 2 h / 20 °C

2: 84 percent / LDA; zirconocene dichloride / tetrahydrofuran / 2 h / -78 °C

3: 85 percent / m-CPBA / CH₂Cl₂ / 2 h / 20 °C

4: 100 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 0 °C

5: aq. H₂O₂; NaOH / tetrahydrofuran / 2 h / 0 °C

6: pyridine / CH₂Cl₂ / 10 h / 20 °C

7: 87 percent / Al-Hg / tetrahydrofuran; aq. ethanol / 96 h / -45 °C

8: 60 percent / imidazole / dimethylformamide / 6 h / 20 °C

9: 70 percent / s-BuLi; CeCl₃ / tetrahydrofuran / 2 h / -40 - 0 °C

10: 73 percent / KH / tetrahydrofuran / 2 h / 20 °C

With pyridine; 1H-imidazole; sodium hydroxide; cerium(III) chloride; aluminium amalgam; zirconocene dichloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; sec.-butyllithium; potassium hydride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: selenylation / 3: Oxidation / 4: desilylation / 5: Epoxidation / 6: Esterification / 7: Reduction / 8: silylation / 9: Alkylation / 10: Hydrolysis;
DOI:10.1016/S0040-4039(99)02103-6