(-)-8-phenylmenthyl (2S,3R,4R)-2,5-dihydroxy-4-methyl-3-phenylpentanoate

Base Information

• Chemical Name: (-)-8-phenylmenthyl (2S,3R,4R)-2,5-dihydroxy-4-methyl-3-phenylpentanoate
• CAS No.: 475503-81-2
• Molecular Formula: C₂₈H₃₈O₄
• Molecular Weight: 438.607
• Mol file: 475503-81-2.mol

Synonyms:(-)-8-phenylmenthyl (2S,3R,4R)-2,5-dihydroxy-4-methyl-3-phenylpentanoate

Chemical Property of (-)-8-phenylmenthyl (2S,3R,4R)-2,5-dihydroxy-4-methyl-3-phenylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-8-phenylmenthyl (2S,3R,4R)-2,5-dihydroxy-4-methyl-3-phenylpentanoate

There total 3 articles about (-)-8-phenylmenthyl (2S,3R,4R)-2,5-dihydroxy-4-methyl-3-phenylpentanoate 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: 99.0%

(-)-8-phenylmenthyl (2S,3R)-2-hydroxy-4-methyl-3-phenylpent-4-enoate (475503-80-1) → (-)-8-phenylmenthyl (2S,3R,4R)-2,5-dihydroxy-4-methyl-3-phenylpentanoate (475503-81-2)

Guidance literature:

(-)-8-phenylmenthyl (2S,3R)-2-hydroxy-4-methyl-3-phenylpent-4-enoate; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 20 ℃; for 12h;

With sodium hydroxide; dihydrogen peroxide; for 0.333333h; Further stages.; sonication;

DOI:10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO;2-3

Reference yield:

(2-methyl-1-propenyl)-benzene (768-49-0) → (-)-8-phenylmenthyl (2S,3R,4R)-2,5-dihydroxy-4-methyl-3-phenylpentanoate (475503-81-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: SnCl₄ / CH₂Cl₂ / 2.5 h / -78 °C

1.2: 81 percent / 19 h / -25 °C

2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 12 h / 20 °C

2.2: 99 percent / NaOH; H₂O₂ / 0.33 h / sonication

With tin(IV) chloride; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane; 1.1: Whitesell ene reaction;

DOI:10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO;2-3

Reference yield:

(1R,3R,4S)-8-phenylmenthyl glyoxylate (84312-20-9) → (-)-8-phenylmenthyl (2S,3R,4R)-2,5-dihydroxy-4-methyl-3-phenylpentanoate (475503-81-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: SnCl₄ / CH₂Cl₂ / 2.5 h / -78 °C

1.2: 81 percent / 19 h / -25 °C

2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 12 h / 20 °C

2.2: 99 percent / NaOH; H₂O₂ / 0.33 h / sonication

With tin(IV) chloride; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane; 1.1: Whitesell ene reaction;

DOI:10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO;2-3

upstream raw materials:

(-)-8-phenylmenthyl (2S,3R)-2-hydroxy-4-methyl-3-phenylpent-4-enoate

(2-methyl-1-propenyl)-benzene

(1R,3R,4S)-8-phenylmenthyl glyoxylate