(1S,3aS,3bR,9bS,11aS)-7-bromo-3a,9b-dimethyl-1-phenyl-1,3,3a,3b,4,5,9b,10,11,11a-decahydrophenanthro[2,1-c]furan

Base Information

• Chemical Name: (1S,3aS,3bR,9bS,11aS)-7-bromo-3a,9b-dimethyl-1-phenyl-1,3,3a,3b,4,5,9b,10,11,11a-decahydrophenanthro[2,1-c]furan
• CAS No.: 1028386-40-4
• Molecular Formula: C₂₄H₂₇BrO
• Molecular Weight: 411.382

Synonyms:(1S,3aS,3bR,9bS,11aS)-7-bromo-3a,9b-dimethyl-1-phenyl-1,3,3a,3b,4,5,9b,10,11,11a-decahydrophenanthro[2,1-c]furan

Chemical Property of (1S,3aS,3bR,9bS,11aS)-7-bromo-3a,9b-dimethyl-1-phenyl-1,3,3a,3b,4,5,9b,10,11,11a-decahydrophenanthro[2,1-c]furan

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Technology Process of (1S,3aS,3bR,9bS,11aS)-7-bromo-3a,9b-dimethyl-1-phenyl-1,3,3a,3b,4,5,9b,10,11,11a-decahydrophenanthro[2,1-c]furan

There total 2 articles about (1S,3aS,3bR,9bS,11aS)-7-bromo-3a,9b-dimethyl-1-phenyl-1,3,3a,3b,4,5,9b,10,11,11a-decahydrophenanthro[2,1-c]furan 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: 51.0%

(R)-((1S,2S,4aS,10aR)-7-bromo-1-(hydroxymethyl)-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-yl)(phenyl)methanol (1028386-44-8) → (1S,3aS,3bR,9bS,11aS)-7-bromo-3a,9b-dimethyl-1-phenyl-1,3,3a,3b,4,5,9b,10,11,11a-decahydrophenanthro[2,1-c]furan (1028386-40-4)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ol800499p

Reference yield: 30.0%

(4S,6S)-4,6-dimethyl-2-phenyl-1,3-dioxane (926892-40-2) + ((2E,6E)-9-(3-bromophenyl)-2,6-dimethylnona-2,6-dienyloxy)triisopropylsilane (1028386-37-9) → (1S,3aS,3bR,9bS,11aS)-7-bromo-3a,9b-dimethyl-1-phenyl-1,3,3a,3b,4,5,9b,10,11,11a-decahydrophenanthro[2,1-c]furan (1028386-40-4) + (2S,4S)-4-((7-bromo-1,4a-dimethyl-1-((triisopropylsilyloxy)methyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-yl)(phenyl)methoxy)pentan-2-ol + (2S,4S)-4-((R)-((1S,2S,4aS,10aR)-7-bromo-1,4a-dimethyl-1-((triisopropylsilyloxy)methyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-yl)(phenyl)methoxy)pentan-2-ol (1028386-35-7) + (2R,4R)-4-((S)-((1R,2R,4aR,10aS)-7-bromo-1,4a-dimethyl-1-((triisopropylsilyloxy)methyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-yl)(phenyl)methoxy)pentan-2-ol

Guidance literature:

With tin(IV) chloride; In dichloromethane; at -78 - -70 ℃; optical yield given as %ee;

DOI:10.1021/ol800499p

upstream raw materials:

(4S,6S)-4,6-dimethyl-2-phenyl-1,3-dioxane

((2E,6E)-9-(3-bromophenyl)-2,6-dimethylnona-2,6-dienyloxy)triisopropylsilane

(R)-((1S,2S,4aS,10aR)-7-bromo-1-(hydroxymethyl)-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-yl)(phenyl)methanol

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