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

Base Information

• Chemical Name: (2S,4R,4aR,8R,8aR)-2-(4-hydroxy-3-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8, 8a-hexahydro-2H-chromene-4,8-diol
• CAS No.: 1292847-81-4
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386
• Mol file: 1292847-81-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (2S,4R,4aR,8R,8aR)-2-(4-hydroxy-3-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8, 8a-hexahydro-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: 28.0%

vanillin (121-33-5,8014-42-4) + (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)-4a,5,8,8a-tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4,4,7-trimethyl-4H-1,3-benzodioxin-8-ol (1292847-79-0) + (2S,4R,4aR,8R,8aR)-2-(4-hydroxy-3-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8, 8a-hexahydro-2H-chromene-4,8-diol (1292847-81-4) + (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-2-(4-hydroxy-3-methoxyphenyl)-4,7-dimethyl-2H-chromene-4,8-diol (1292847-80-3)

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: 14.0%

vanillin (121-33-5,8014-42-4) + (1R,2R,4S,5R,6S)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.04.2]octan-5-ol (176705-36-5) → 2-hydroxy-1-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]ethanone + (2S,4R,4aR,8R,8aR)-2-(4-hydroxy-3-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8, 8a-hexahydro-2H-chromene-4,8-diol (1292847-81-4) + (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-2-(4-hydroxy-3-methoxyphenyl)-4,7-dimethyl-2H-chromene-4,8-diol (1292847-80-3) + C10H16O2

Guidance literature:

With montmorillonite K₁₀ clay; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1007/s00044-015-1426-5

Reference yield:

(1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol (935670-67-0) + vanillin (121-33-5,8014-42-4) → (2S,4R,4aR,8R,8aR)-2-(4-hydroxy-3-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8, 8a-hexahydro-2H-chromene-4,8-diol (1292847-81-4) + (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-2-(4-hydroxy-3-methoxyphenyl)-4,7-dimethyl-2H-chromene-4,8-diol (1292847-80-3) + (2R,4S,4aR,6S,7R,8aR,9S)2,9-bis(4-hydroxy-3-methoxyphenyl)-4,7-dimethylhexahydro-2H-4,6-(epoxymethano)chromen-8(8aH)-one

Guidance literature:

With montmorillonite K₁₀ Clay; In dichloromethane; at 20 ℃; for 72h; stereoselective reaction;

DOI:10.1007/s11172-015-1148-3

upstream raw materials:

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

vanillin

4-hydroxy-benzaldehyde

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