1,2-Cyclohexanedicarboxylic acid, 4-hydroxy-5-(phenylseleno)-, bis[(1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl] ester, (1R,2R,4R,5R)-

Base Information

• Chemical Name: 1,2-Cyclohexanedicarboxylic acid, 4-hydroxy-5-(phenylseleno)-, bis[(1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl] ester, (1R,2R,4R,5R)-
• CAS No.: 479549-19-4
• Molecular Formula: C34H52O5Se
• Molecular Weight: 619.744
• Mol file: 479549-19-4.mol

Synonyms:

Chemical Property of 1,2-Cyclohexanedicarboxylic acid, 4-hydroxy-5-(phenylseleno)-, bis[(1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl] ester, (1R,2R,4R,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Cyclohexanedicarboxylic acid, 4-hydroxy-5-(phenylseleno)-, bis[(1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl] ester, (1R,2R,4R,5R)-

There total 4 articles about 1,2-Cyclohexanedicarboxylic acid, 4-hydroxy-5-(phenylseleno)-, bis[(1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl] ester, (1R,2R,4R,5R)- 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: 75.0%

Phenylselenyl bromide (34837-55-3) + (1R,2R,1'S,2'R,5'S)-cyclohex-4-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester (73627-88-0,109062-95-5,110416-37-0,122044-47-7) → (1R,2R,4R,5R,1'S,2'R,5'S)-4-hydroxy-5-phenylselanyl-cyclohexane-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester (479549-19-4)

Guidance literature:

With water; In acetonitrile; at 50 ℃; for 12h;

DOI:10.1002/1521-3773(20020802)41:15<2786::AID-ANIE2786>3.0.CO;2-Z

Reference yield:

(2E,1'S,2'R,5'S)-but-2-enedioic acid bis(2'-isopropyl-5'methyl-cyclohexyl) ester (86287-64-1) → (1R,2R,4R,5R,1'S,2'R,5'S)-4-hydroxy-5-phenylselanyl-cyclohexane-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester (479549-19-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₂AlCl / toluene; hexane / 0.67 h / -60 °C

1.2: 73 percent / toluene; hexane / 36 h / -60 °C

2.1: 75 percent / acetonitrile; H₂O / 12 h / 50 °C

With diethylaluminium chloride; In hexane; water; toluene; acetonitrile; 1.2: Diels-Alder reaction;

DOI:10.1016/S0040-4020(03)00816-0

Reference yield:

(1S,2R,5S)-(+)-menthol (15356-60-2) → (1R,2R,4R,5R,1'S,2'R,5'S)-4-hydroxy-5-phenylselanyl-cyclohexane-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester (479549-19-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / p-TsOH*H₂O / toluene / 17 h / Heating

2.1: 81 percent / morpholine / toluene / 10 h / 100 °C

3.1: Et₂AlCl / toluene; hexane / 0.67 h / -60 °C

3.2: 73 percent / toluene; hexane / 36 h / -60 °C

4.1: 75 percent / acetonitrile; H₂O / 12 h / 50 °C

With morpholine; diethylaluminium chloride; toluene-4-sulfonic acid; In hexane; water; toluene; acetonitrile; 3.2: Diels-Alder reaction;

DOI:10.1016/S0040-4020(03)00816-0

upstream raw materials:

Phenylselenyl bromide

(1R,2R,1'S,2'R,5'S)-cyclohex-4-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester

(1S,2R,5S)-(+)-menthol

(2E,1'S,2'R,5'S)-but-2-enedioic acid bis(2'-isopropyl-5'methyl-cyclohexyl) ester

Downstream raw materials:

(1R,2R,3Z,5R,1'S,2'R,5'S)-5-hydroxy-cyclohex-3-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester

epi,epi-(3''S,4''S)-polycephalin C

C₄₄H₆₄N₂O₈Si₂

(1R,2R,3Z,5R,1'S,2'R,5'S)-5-methanesulfonyloxy-cyclohex-3-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester