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

Base Information

• Chemical Name: (-)-8-phenylmenthyl (2S,3R)-2-hydroxy-4-methyl-3-phenylpent-4-enoate
• CAS No.: 475503-80-1
• Molecular Formula: C₂₈H₃₆O₃
• Molecular Weight: 420.592
• Mol file: 475503-80-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (-)-8-phenylmenthyl (2S,3R)-2-hydroxy-4-methyl-3-phenylpent-4-enoate 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: 81.0%

(2-methyl-1-propenyl)-benzene (768-49-0) + (1R,3R,4S)-8-phenylmenthyl glyoxylate (84312-20-9) → (-)-8-phenylmenthyl (2S,3R)-2-hydroxy-4-methyl-3-phenylpent-4-enoate (475503-80-1)

Guidance literature:

(2-methyl-1-propenyl)-benzene; (1R,3R,4S)-8-phenylmenthyl glyoxylate; With tin(IV) chloride; In dichloromethane; at -78 ℃; for 2.5h;

at -25 ℃; for 19h; Further stages.;

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

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: 94.0%

t-butyldimethylsiyl triflate (69739-34-0) + (-)-8-phenylmenthyl (2S,3R)-2-hydroxy-4-methyl-3-phenylpent-4-enoate (475503-80-1) → (-)-8-phenylmenthyl (2S,3R)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenylpent-4-enoate

Guidance literature:

With 2,6-dimethylpyridine; dmap; In dichloromethane; at 20 ℃; for 2.5h;

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

upstream raw materials:

(2-methyl-1-propenyl)-benzene

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

Downstream raw materials:

(2S,3R)-2-hydroxy-4-methyl-3-phenylpent-4-enoic acid

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

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

(2S,3R,4S)-2-hydroxy-4-methyl-3-phenyl-δ-valerolactone