(2R,4S,4aR,6S,7R,8aR,9S)-hexahydro-2,9-bis(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-2H-4,6-(epoxymethano)chromen-8(5H)-one

Base Information

• Chemical Name: (2R,4S,4aR,6S,7R,8aR,9S)-hexahydro-2,9-bis(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-2H-4,6-(epoxymethano)chromen-8(5H)-one
• CAS No.: 1292847-76-7
• Molecular Formula: C₂₆H₃₀O₇
• Molecular Weight: 454.52
• Mol file: 1292847-76-7.mol

Synonyms:

Chemical Property of (2R,4S,4aR,6S,7R,8aR,9S)-hexahydro-2,9-bis(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-2H-4,6-(epoxymethano)chromen-8(5H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,4aR,6S,7R,8aR,9S)-hexahydro-2,9-bis(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-2H-4,6-(epoxymethano)chromen-8(5H)-one

There total 6 articles about (2R,4S,4aR,6S,7R,8aR,9S)-hexahydro-2,9-bis(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-2H-4,6-(epoxymethano)chromen-8(5H)-one 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: 8.0%

isovanillin (621-59-0) + (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol (935670-67-0) → (2S,4aR,8R,8aR)-4a,5,8,8a-tetrahydro-2-(3-hydroxy-4-methoxyphenyl)-4,4,7-trimethyl-4H-1,3-benzodioxin-8-ol (1292847-82-5) + (2S,4R,4aR,8R,8aR)-2-(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8, 8a-hexahydro-2H-chromene-4,8-diol (1292847-88-1) + (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-2-(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-2H-chromene-4,8-diol (1292847-83-6) + (2R,4S,4aR,6S,7R,8aR,9S)-hexahydro-2,9-bis(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-2H-4,6-(epoxymethano)chromen-8(5H)-one (1292847-76-7)

Guidance literature:

With montmorillonite K 10; at 20 ℃; for 96h; optical yield given as %de; Neat (no solvent);

DOI:10.1002/hlca.201000269

Reference yield: 8.0%

isovanillin (621-59-0) + (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol (935670-67-0) → (2R,4S,4aR,6S,7R,8aR,9S)-hexahydro-2,9-bis(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-2H-4,6-(epoxymethano)chromen-8(5H)-one (1292847-76-7) + (2S,4aR,8R,8aR)-2-(4-hydroxy-3-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diol

Guidance literature:

With montmorillonite K₁₀ Clay; stereoselective reaction;

DOI:10.1007/s11172-015-1148-3

Reference yield:

benzaldehyde (100-52-7) → (2S,4aR,8R,8aR)-4a,5,8,8a-tetrahydro-2-(3-hydroxy-4-methoxyphenyl)-4,4,7-trimethyl-4H-1,3-benzodioxin-8-ol (1292847-82-5) + (2S,4R,4aR,8R,8aR)-2-(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8, 8a-hexahydro-2H-chromene-4,8-diol (1292847-88-1) + (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-2-(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-2H-chromene-4,8-diol (1292847-83-6) + (2R,4S,4aR,6S,7R,8aR,9S)-hexahydro-2,9-bis(3-hydroxy-4-methoxyphenyl)-4,7-dimethyl-2H-4,6-(epoxymethano)chromen-8(5H)-one (1292847-76-7)

Guidance literature:

Multi-step reaction with 2 steps

1: montmorillonite K 10 / dichloromethane / 0.67 h / 20 °C

2: montmorillonite K 10 / 96 h / 20 °C / Neat (no solvent)

With montmorillonite K 10; In dichloromethane;

DOI:10.1002/hlca.201000269

upstream raw materials:

isovanillin

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

benzaldehyde

4-hydroxy-benzaldehyde