5-[(3aS,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-enyl]-hexahydro-cyclopenta[b]pyrrol-(2Z)-ylidene]-4-oxo-pentanoic acid methyl ester

Base Information

Chemical Name:5-[(3aS,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-enyl]-hexahydro-cyclopenta[b]pyrrol-(2Z)-ylidene]-4-oxo-pentanoic acid methyl ester
CAS No.:111803-72-6
Molecular Formula:C₃₅H₅₇NO₆Si₂
Molecular Weight:644.012
Hs Code.:

5-[(3aS,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-enyl]-hexahydro-cyclopenta[b]pyrrol-(2Z)-ylidene]-4-oxo-pentanoic acid methyl ester

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Chemical Property of 5-[(3aS,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-enyl]-hexahydro-cyclopenta[b]pyrrol-(2Z)-ylidene]-4-oxo-pentanoic acid methyl ester

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Technology Process of 5-[(3aS,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-enyl]-hexahydro-cyclopenta[b]pyrrol-(2Z)-ylidene]-4-oxo-pentanoic acid methyl ester

There total 34 articles about 5-[(3aS,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-enyl]-hexahydro-cyclopenta[b]pyrrol-(2Z)-ylidene]-4-oxo-pentanoic acid methyl 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%

: 111803-75-9,111901-10-1
5-{(3aS,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-enyl]-3,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrol-2-ylsulfanyl}-4-oxo-pentanoic acid methyl ester

: 111803-72-6,111901-07-6
5-[(3aS,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-enyl]-hexahydro-cyclopenta[b]pyrrol-(2Z)-ylidene]-4-oxo-pentanoic acid methyl ester

Guidance literature:: With potassium tert-butylate; triphenylphosphine; In xylene; tert-butyl alcohol; Heating;
DOI:10.1139/v87-362

Reference yield: 68.0%

: 111803-75-9,111901-10-1
5-{(3aS,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-enyl]-3,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrol-2-ylsulfanyl}-4-oxo-pentanoic acid methyl ester

: 111803-72-6,111901-07-6
5-[(3aS,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-enyl]-hexahydro-cyclopenta[b]pyrrol-(2Z)-ylidene]-4-oxo-pentanoic acid methyl ester

Guidance literature:: With potassium tert-butylate; triphenylphosphine; In xylene; tert-butyl alcohol; Heating;
DOI:10.1139/v87-362

Reference yield:

: 111803-49-7
(3aR,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-1H-cyclopenta[b]pyrrol-2-one

: 111803-72-6,111901-07-6
5-[(3aS,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-enyl]-hexahydro-cyclopenta[b]pyrrol-(2Z)-ylidene]-4-oxo-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 72 percent / N-bromosuccinimide, water / dimethylsulfoxide / 1 h / 10 - 20 °C

2: 71 percent / pyridine / 2 h / Ambient temperature

3: 85 percent / tri-n-butyltin hydride, azobisisobutyronitrile / benzene / 4 h / 60 °C

4: 94 percent / H₂ / 10percent palladium on charcoal / 1,2-dimethoxy-ethane; HClO₄ / 10 h / Ambient temperature

5: 3.5 g / Collins reagent, Celite / CH₂Cl₂ / 0.25 h / 0 - 5 °C

6: 19 percent / 1.) NaH / 1,2-dimethoxy-ethane / Ambient temperature; 1.) 0.5 h 2.) 3 h

7: 37 percent / 1.) cerous chloride hexahydrate 2.) NaBH₄ / methanol; tetrahydrofuran / 0 °C

8: 85 percent / potassium carbonate / methanol; tetrahydrofuran / 3 h / Ambient temperature

9: 76 percent / imidazole / dimethylformamide

10: 80 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) / benzene / Heating

11: 1.) NaH / tetrahydrofuran / 1.) rt., 1 h 2.) 0 deg C

12: 68 percent / triphenylphosphine, t-BuOK / xylene; 2-methyl-propan-2-ol / Heating

With Lawessons reagent; pyridine; 1H-imidazole; sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); Collins oxidation agent; Celite; potassium tert-butylate; water; hydrogen; tri-n-butyl-tin hydride; sodium hydride; potassium carbonate; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; perchloric acid; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; xylene; tert-butyl alcohol; benzene;
DOI:10.1139/v87-362