(1S,2R,3S,4R,5R,6R)-6-((1S,3R)-1-Allyl-3-hydroxy-hex-5-enyloxy)-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Base Information

Chemical Name:(1S,2R,3S,4R,5R,6R)-6-((1S,3R)-1-Allyl-3-hydroxy-hex-5-enyloxy)-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde
CAS No.:816455-37-5
Molecular Formula:C₂₄H₃₁BrO₃
Molecular Weight:447.412
Hs Code.:

Synonyms:(1S,2R,3S,4R,5R,6R)-6-((1S,3R)-1-Allyl-3-hydroxy-hex-5-enyloxy)-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde

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Chemical Property of (1S,2R,3S,4R,5R,6R)-6-((1S,3R)-1-Allyl-3-hydroxy-hex-5-enyloxy)-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde

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Technology Process of (1S,2R,3S,4R,5R,6R)-6-((1S,3R)-1-Allyl-3-hydroxy-hex-5-enyloxy)-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde

There total 11 articles about (1S,2R,3S,4R,5R,6R)-6-((1S,3R)-1-Allyl-3-hydroxy-hex-5-enyloxy)-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde 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:

: (1R,2R,3R,5S,7R,9R,10R,11S,13S)-5,7-Diallyl-2-bromo-9-methoxy-10-methyl-13-phenyl-4,8-dioxa-tricyclo[8.2.1.0^3,11]tridecane

: 816455-37-5
(1S,2R,3S,4R,5R,6R)-6-((1S,3R)-1-Allyl-3-hydroxy-hex-5-enyloxy)-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Guidance literature:: With toluene-4-sulfonic acid; In acetone; at 20 ℃;
DOI:10.1002/chem.200400444

Reference yield:

: 816454-32-7,816454-13-4,816454-36-1
(1R,2S,3S,4S)-2-exo-methyl-3-endo-phenylnorbornene-2-carbaldehyde

: 816455-37-5
(1S,2R,3S,4R,5R,6R)-6-((1S,3R)-1-Allyl-3-hydroxy-hex-5-enyloxy)-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / p-TsOH / toluene / 24 h / 20 °C

2: NBS / -40 - 20 °C

3: 66.8 mg / aq. p-TsOH / acetone / 20 °C

With N-Bromosuccinimide; toluene-4-sulfonic acid; In acetone; toluene;
DOI:10.1002/chem.200400444

Reference yield:

: methyl 3-phenylnorbornene-2-carboxylate

: 816455-37-5
(1S,2R,3S,4R,5R,6R)-6-((1S,3R)-1-Allyl-3-hydroxy-hex-5-enyloxy)-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 76 percent / tetrahydrofuran / 12 h / 20 °C

2.1: 97 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

3.1: 95 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: p-TsOH / toluene / 3 h / 20 °C

4.2: 36 percent / aq. NBS / acetonitrile / 20 h / 20 °C

5.1: Zn(OTf)2 / N,N-dimethyl-acetamide / 0.5 h / 40 °C

5.2: 85 percent / Zn / N,N-dimethyl-acetamide / 5 h / 70 °C

6.1: 90 percent / p-TsOH / toluene / 24 h / 20 °C

7.1: NBS / -40 - 20 °C

8.1: 66.8 mg / aq. p-TsOH / acetone / 20 °C

With N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; zinc trifluoromethanesulfonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; acetone; toluene; 3.1: Swern oxidation;
DOI:10.1002/chem.200400444