(-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-([1,3]dioxolan-2-yl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene

Base Information

Chemical Name:(-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-([1,3]dioxolan-2-yl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene
CAS No.:345222-83-5
Molecular Formula:C₂₅H₃₂Br₂O₃
Molecular Weight:540.335
Hs Code.:

Synonyms:(-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-([1,3]dioxolan-2-yl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene

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Chemical Property of (-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-([1,3]dioxolan-2-yl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene

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Technology Process of (-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-([1,3]dioxolan-2-yl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene

There total 5 articles about (-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-([1,3]dioxolan-2-yl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene 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: 41.0%

: 150252-11-2
tert-butyl (1S,3aS,7aS)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-1-yl ether

: 446265-57-2
1,4-dibromo-2-[(Z)-2-bromovinyl]-5-[1,3]dioxolan-2-ylbenzene

: 345222-83-5
(-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-([1,3]dioxolan-2-yl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene

Guidance literature:: With tetrabutylammonium acetate; triphenylphosphine; palladium diacetate; In water; N,N-dimethyl-formamide; acetonitrile; at 60 ℃; for 16h;
DOI:10.1055/s-2001-12438

Reference yield:

: 63525-48-4
2,5-dibromoterephthalaldehyde

: 345222-83-5
(-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-([1,3]dioxolan-2-yl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene

Guidance literature:: Multi-step reaction with 4 steps

1: PPh₃ / CH₂Cl₂ / 0.5 h / -20 °C

2: pTsOH / toluene / 1.5 h / Heating

3: 98 percent / Bu₃SnH / Pd(PPh₃)4 / toluene / 1 h / 20 °C

4: 41 percent / PPh₃; nBu₄NOAc / Pd(OAc)2 / dimethylformamide; acetonitrile; H₂O / 16 h / 60 °C

With tri-n-butyl-tin hydride; tetrabutylammonium acetate; toluene-4-sulfonic acid; triphenylphosphine; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Corey-Fuchs reaction / 4: Heck reaction;
DOI:10.1055/s-2001-12438

Reference yield:

: 345222-81-3
1,4-dibromo-2-(2,2-dibromovinyl)-5-[1,3]dioxolan-2-ylbenzene

: 345222-83-5
(-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-([1,3]dioxolan-2-yl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / n-Bu₃SnH / [Pd(PPh₃)4] / toluene / 1.5 h / 20 °C

2: 41 percent / aq. n-Bu₄NOAc; PPh₃ / Pd(OAc)2 / dimethylformamide; acetonitrile / 21 h / 60 °C

With tri-n-butyl-tin hydride; tetrabutylammonium acetate; triphenylphosphine; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; toluene; acetonitrile; 2: Heck reaction;
DOI:10.1002/1521-3765(20020503)8:9<2116::AID-CHEM2116>3.0.CO;2-4