(2R,3R,3aS,6aS)-5-[5-(tert-Butyl-diphenyl-silanyloxy)-pentyl]-3-((E)-(R)-3-hydroxy-oct-1-enyl)-1,2,3,3a,4,6a-hexahydro-pentalen-2-ol

Base Information

Chemical Name:(2R,3R,3aS,6aS)-5-[5-(tert-Butyl-diphenyl-silanyloxy)-pentyl]-3-((E)-(R)-3-hydroxy-oct-1-enyl)-1,2,3,3a,4,6a-hexahydro-pentalen-2-ol
CAS No.:210296-19-8
Molecular Formula:C₃₇H₅₄O₃Si
Molecular Weight:574.919
Hs Code.:

Synonyms:(2R,3R,3aS,6aS)-5-[5-(tert-Butyl-diphenyl-silanyloxy)-pentyl]-3-((E)-(R)-3-hydroxy-oct-1-enyl)-1,2,3,3a,4,6a-hexahydro-pentalen-2-ol

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Chemical Property of (2R,3R,3aS,6aS)-5-[5-(tert-Butyl-diphenyl-silanyloxy)-pentyl]-3-((E)-(R)-3-hydroxy-oct-1-enyl)-1,2,3,3a,4,6a-hexahydro-pentalen-2-ol

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Technology Process of (2R,3R,3aS,6aS)-5-[5-(tert-Butyl-diphenyl-silanyloxy)-pentyl]-3-((E)-(R)-3-hydroxy-oct-1-enyl)-1,2,3,3a,4,6a-hexahydro-pentalen-2-ol

There total 12 articles about (2R,3R,3aS,6aS)-5-[5-(tert-Butyl-diphenyl-silanyloxy)-pentyl]-3-((E)-(R)-3-hydroxy-oct-1-enyl)-1,2,3,3a,4,6a-hexahydro-pentalen-2-ol 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: 5.0%

: 210296-16-5
Acetic acid (2R,3R,3aS,6aS)-3-((E)-(R)-3-acetoxy-oct-1-enyl)-5-[5-(tert-butyl-diphenyl-silanyloxy)-pentyl]-1,2,3,3a,4,6a-hexahydro-pentalen-2-yl ester

: 210296-17-6
Acetic acid (2R,3R,3aS,6aS)-3-((E)-(S)-3-acetoxy-oct-1-enyl)-5-(5-hydroxy-pentyl)-1,2,3,3a,4,6a-hexahydro-pentalen-2-yl ester

: 210296-19-8
(2R,3R,3aS,6aS)-5-[5-(tert-Butyl-diphenyl-silanyloxy)-pentyl]-3-((E)-(R)-3-hydroxy-oct-1-enyl)-1,2,3,3a,4,6a-hexahydro-pentalen-2-ol

Guidance literature:: With potassium carbonate; In methanol; for 4h; Ambient temperature;

Reference yield:

: 112755-94-9,92007-37-9
(3a'R,6a'S)-5,5-dimethyltetrahydro-1'H-spiro[1,3-dioxane-2,2'-pentalen]-5'(3'H)-one

: 210296-19-8
(2R,3R,3aS,6aS)-5-[5-(tert-Butyl-diphenyl-silanyloxy)-pentyl]-3-((E)-(R)-3-hydroxy-oct-1-enyl)-1,2,3,3a,4,6a-hexahydro-pentalen-2-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 86 percent / 1.) n-BuLi; 2.) ClSiMe₃, n-BuLi / tetrahydrofuran; hexane / 1.) -60 deg C, -> room temp., then -78 deg C, 30 min; 2.) -90 deg C -> room temp., then room temp., 3 h, then -90 deg C, 30 min

2: 88 percent / LiOMe, phenanthroline / tetrahydrofuran; toluene / 0 deg C -> room temp., 10 h, then room temp., 2 d

3: 95 percent / Me₂S / diethyl ether / 6 h / -45 °C

4: 77 percent / p-TsOH / acetone; H₂O / 24 h / Ambient temperature

5: 80 percent / imidazole / dimethylformamide / 0.67 h / 0 °C

6: 1.) (R,R)-bis(α-phenylethyl)ammonium chloride, n-BuLi / 1.) THF, hexane, -72 deg C, 10 min, then -100 deg C, 2 h; 2.) THF, hexane, -108 - -104 deg C, 35 min, then -70 deg C, 3 h

7: 88 percent / NaBH₄ / ethanol / 7 h / -40 °C / 1.) -66 deg C

8: 98 percent / pyridine / tetrahydrofuran / 23 h / Ambient temperature

9: Pd(MeCN)2Cl₂ / tetrahydrofuran / 17 h / Ambient temperature

10: 94 percent / K₂CO₃ / methanol / 4 h / Ambient temperature

With pyridine; 1H-imidazole; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; n-butyllithium; chloro-trimethyl-silane; Phenanthroline; dimethylsulfide; lithium methanolate; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; water; N,N-dimethyl-formamide; acetone; toluene;

Reference yield:

: 2548-87-0
(E)-2-Octenal

: 210296-19-8
(2R,3R,3aS,6aS)-5-[5-(tert-Butyl-diphenyl-silanyloxy)-pentyl]-3-((E)-(R)-3-hydroxy-oct-1-enyl)-1,2,3,3a,4,6a-hexahydro-pentalen-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) (R,R)-bis(α-phenylethyl)ammonium chloride, n-BuLi / 1.) THF, hexane, -72 deg C, 10 min, then -100 deg C, 2 h; 2.) THF, hexane, -108 - -104 deg C, 35 min, then -70 deg C, 3 h

2: 88 percent / NaBH₄ / ethanol / 7 h / -40 °C / 1.) -66 deg C

3: 98 percent / pyridine / tetrahydrofuran / 23 h / Ambient temperature

4: Pd(MeCN)2Cl₂ / tetrahydrofuran / 17 h / Ambient temperature

5: 94 percent / K₂CO₃ / methanol / 4 h / Ambient temperature

With pyridine; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; n-butyllithium; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; potassium carbonate; In tetrahydrofuran; methanol; ethanol;