(1S,2S,3S,5R,6S,8S,9S,10R,12S)-2-Bromo-8-methoxy-5,6-dimethyl-12-phenyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane

Base Information

• Chemical Name: (1S,2S,3S,5R,6S,8S,9S,10R,12S)-2-Bromo-8-methoxy-5,6-dimethyl-12-phenyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane
• CAS No.: 271578-39-3
• Molecular Formula: C₁₉H₂₅BrO₃
• Molecular Weight: 381.31

Synonyms:(1S,2S,3S,5R,6S,8S,9S,10R,12S)-2-Bromo-8-methoxy-5,6-dimethyl-12-phenyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane

Chemical Property of (1S,2S,3S,5R,6S,8S,9S,10R,12S)-2-Bromo-8-methoxy-5,6-dimethyl-12-phenyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane

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Technology Process of (1S,2S,3S,5R,6S,8S,9S,10R,12S)-2-Bromo-8-methoxy-5,6-dimethyl-12-phenyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane

There total 4 articles about (1S,2S,3S,5R,6S,8S,9S,10R,12S)-2-Bromo-8-methoxy-5,6-dimethyl-12-phenyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane 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: 88.0%

methanol (67-56-1) + (2S,4R,5S)-4,5-Dimethyl-2-((1S,2R,3R,4R)-3-phenyl-bicyclo[2.2.1]hept-5-en-2-yl)-[1,3]dioxolane (271578-38-2) → (1S,2S,3S,5R,6S,8S,9S,10R,12S)-2-Bromo-8-methoxy-5,6-dimethyl-12-phenyl-4,7-dioxa-tricyclo[7.2.1.03,10]dodecane (271578-39-3)

Guidance literature:

With N-Bromosuccinimide; In methanol;

DOI:10.1016/S0040-4039(00)00039-3

Reference yield:

endo-3-phenylbicyclo[2.2.1]hept-5-ene-2-carboxaldehyde (123364-25-0,123410-32-2) → (1S,2S,3S,5R,6S,8S,9S,10R,12S)-2-Bromo-8-methoxy-5,6-dimethyl-12-phenyl-4,7-dioxa-tricyclo[7.2.1.03,10]dodecane (271578-39-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: PPTS / toluene / 20 °C

1.2: 43 percent / NBS; H₂O / acetonitrile / 20 °C

2.1: 98 percent / Zn; Zn(OTf)2; DMA / 80 - 90 °C

3.1: 100 percent

4.1: 88 percent / NBS / methanol

With N-Bromosuccinimide; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; 2,4-dichlorophenoxyacetic acid dimethylamine; zinc; In methanol; toluene; 1.1: cycloacetalization / 1.2: Bromination / 2.1: debromoetherification / 3.1: cycloacetalization / 4.1: Etherification;

DOI:10.1016/S0040-4039(00)00039-3

Reference yield:

(1S,2R,3R,4R)-3-phenylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde (271578-35-9) → (1S,2S,3S,5R,6S,8S,9S,10R,12S)-2-Bromo-8-methoxy-5,6-dimethyl-12-phenyl-4,7-dioxa-tricyclo[7.2.1.03,10]dodecane (271578-39-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent

2: 88 percent / NBS / methanol

With N-Bromosuccinimide; In methanol; 1: cycloacetalization / 2: Etherification;

DOI:10.1016/S0040-4039(00)00039-3

upstream raw materials:

methanol

(2S,4R,5S)-4,5-Dimethyl-2-((1S,2R,3R,4R)-3-phenyl-bicyclo[2.2.1]hept-5-en-2-yl)-[1,3]dioxolane

endo-3-phenylbicyclo[2.2.1]hept-5-ene-2-carboxaldehyde

(1S,2R,3R,4R)-3-phenylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde

Downstream raw materials:

(2R,3S)-3-[(S)-Methoxy-((1S,2R,3R,4R)-3-phenyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-butan-2-ol

(1R,4S,5R,6R)-5-[(S)-((1S,2R)-2-Benzyloxy-1-methyl-propoxy)-methoxy-methyl]-6-phenyl-bicyclo[2.2.1]hept-2-ene

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