(2R,3R)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester

Base Information

• Chemical Name: (2R,3R)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester
• CAS No.: 244178-02-7
• Molecular Formula: C₁₆H₂₂O₂S
• Molecular Weight: 278.415
• Mol file: 244178-02-7.mol

Synonyms:(2R,3R)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester

Chemical Property of (2R,3R)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester

There total 4 articles about (2R,3R)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester 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: 90.0%

phenylmethanethiol (100-53-8) + (2R,3R)-3-hydroxy-2-isobutylpent-4-enoic acid (244178-00-5) → (2R,3R)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester (244178-02-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/ol006560k

Reference yield:

(2R,3R)-3-Hydroxy-2-isobutyl-pent-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester (244177-97-7) → (2R,3R)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester (244178-02-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / NaOH / methanol; H₂O / 14 h / 20 °C

2: 90 percent / DCC; DMAP / CH₂Cl₂ / 4 h / 20 °C

With dmap; sodium hydroxide; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water; 1: Hydrolysis / 2: Substitution;

DOI:10.1021/ol006560k

Reference yield:

(1R,2S)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl 4-methylpentanoate (244177-94-4) → (2R,3R)-3-hydroxy-2-isobutylpent-4-enethioic acid S-benzyl ester (244178-02-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Cx₂BOTf; Et₃N / CH₂Cl₂ / 2 h / -78 °C

1.2: 5.2 g / CH₂Cl₂ / -78 - 0 °C

2.1: 85 percent / NaOH / methanol; H₂O / 14 h / 20 °C

3.1: 90 percent / DCC; DMAP / CH₂Cl₂ / 4 h / 20 °C

With dmap; sodium hydroxide; Cx₂BOTf; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water; 1.1: Addition / 1.2: Condensation / 2.1: Hydrolysis / 3.1: Substitution;

DOI:10.1021/ol006560k

upstream raw materials:

phenylmethanethiol

(2R,3R)-3-hydroxy-2-isobutylpent-4-enoic acid

(1R,2S)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl 4-methylpentanoate

(2R,3R)-3-Hydroxy-2-isobutyl-pent-4-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

Downstream raw materials:

(2R,3R,6S,7S)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester

(2R,3R,6R,7S)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester

(2R,3R,6S,7R)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester

(2R,3R,6R,7R)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester