methyl (3S,4R)-3-hydroxy-4-phenylpentanoate

Base Information

• Chemical Name: methyl (3S,4R)-3-hydroxy-4-phenylpentanoate
• CAS No.: 36041-82-4
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.257
• Mol file: 36041-82-4.mol

Synonyms:

Chemical Property of methyl (3S,4R)-3-hydroxy-4-phenylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3S,4R)-3-hydroxy-4-phenylpentanoate

There total 8 articles about methyl (3S,4R)-3-hydroxy-4-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:

ketene t-butyldimethylsilyl methyl acetal (77086-38-5) + (R)-2-phenylpropanal (93-53-8) → (3R,4R)-3-Hydroxy-4-phenyl-pentanoic acid methyl ester (36041-82-4,36041-83-5) + methyl (3S,4R)-3-hydroxy-4-phenylpentanoate (36041-82-4,36041-83-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/ja00344a050

Reference yield:

ketene t-butyldimethylsilyl methyl acetal (77086-38-5) + (R)-2-phenylpropanal (93-53-8) → (3R,4R)-3-Hydroxy-4-phenyl-pentanoic acid methyl ester (36041-82-4,36041-83-5) + methyl (3S,4R)-3-hydroxy-4-phenylpentanoate (36041-82-4,36041-83-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/ja00344a050

Reference yield:

methyl (E)-4-phenylpent-3-enoate → methyl (3R,4S)-3-hydroxy-4-phenylpentanoate (36041-82-4,36041-83-5) + methyl (3S,4R)-3-hydroxy-4-phenylpentanoate (36041-82-4,36041-83-5)

Guidance literature:

methyl (E)-4-phenylpent-3-enoate; With monoisopinocampheylborane; In tetrahydrofuran; at -25 ℃; for 48h;

With methanol; In tetrahydrofuran; at -25 ℃;

With dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2012.10.047

upstream raw materials:

(S)-2-phenyl-propionaldehyde

bromoacetic acid methyl ester

4-phenyl-3-pentenoic acid

ketene t-butyldimethylsilyl methyl acetal

Downstream raw materials:

(3R,4S)-4-phenylpentane-1,3-diol

(2S,3R)-threo-2-phenylpentan-3-ol

Refernces

• 1、 Heathcock, Clayton H.,Flippin, Lee A.. "Acyclic Stereoselection. 16. High Diastereofacial Selectivity in Lewis Acid Mediated Additions of Enolsilanes to Chiral Aldehydes". . p. 1667 - 1668. Retrieved 2007/10/02.