(2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol

Base Information

• Chemical Name: (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol
• CAS No.: 1292847-75-6
• Molecular Formula: C₁₇H₂₂O₃
• Molecular Weight: 274.36

Synonyms:(2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol

Chemical Property of (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol

Chemical Property:

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Technology Process of (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol

There total 5 articles about (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol 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: 16.0%

benzaldehyde (100-52-7) + (1R,2R,4S,5R,6S)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.04.2]octan-5-ol (176705-36-5) → (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol (935670-67-0) + 2-hydroxy-1-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]ethanone + (2S,4aR,8R,8aR)-4,4,7-trimethyl-2-phenyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol (1292847-77-8) + (2S,4R,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol + (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol (1292847-75-6)

Guidance literature:

With montmorillonite K 10; In dichloromethane; at 20 ℃; for 0.666667h; optical yield given as %de;

DOI:10.1002/hlca.201000269

Reference yield:

(1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol (935670-67-0) + benzaldehyde (100-52-7) → (2S,4R,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol + (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol (1292847-75-6)

Guidance literature:

With K₁₀ montmorillonite clay; In dichloromethane; at 20 ℃; for 24h; Overall yield = 43 %;

DOI:10.1007/s10600-017-2202-1

Reference yield:

(1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol (935670-67-0) + benzaldehyde (100-52-7) → (2S,4R,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol + (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol (1292847-75-6) + C17H21FO2 + C17H21FO2

Guidance literature:

With boron trifluoride diethyl etherate; water; In dichloromethane; at 2 ℃;

DOI:10.1016/j.bmc.2016.08.037

upstream raw materials:

benzaldehyde

(1R,2R,4S,5R,6S)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0^4.2]octan-5-ol

(1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol

(-)-Verbenone

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