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

Base Information

• Chemical Name: (1R,2S)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl 4-methylpentanoate
• CAS No.: 244177-94-4
• Molecular Formula: C₃₁H₃₉NO₄S
• Molecular Weight: 521.721
• Mol file: 244177-94-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (1R,2S)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl 4-methylpentanoate 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:

4-methylvaleroyl chloride (38136-29-7) + (1R,2S)-2-[N-benzyl-N-(mesitylenesulfonyl)amino]-1-phenyl-1-propanol (187324-63-6) → (1R,2S)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl 4-methylpentanoate (244177-94-4)

Guidance literature:

With pyridine; In tetrahydrofuran; at 20 ℃; for 16h;

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,6R,7R)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester (318957-66-3)

Guidance literature:

Multi-step reaction with 8 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: imidazole / dimethylformamide / 24 h / 20 °C

3.2: H₂O / tetrahydrofuran; methanol / 4 h / 20 °C

4.1: (PhO)2PON₃; Et₃N / acetonitrile / 0.5 h / Heating

4.2: CuCl / acetonitrile / 2 h / 20 °C

5.1: AcOH / tetrahydrofuran; H₂O / 0.07 h / 55 °C

6.1: pyridine / 2 h / 20 °C

6.2: pyridine / 1.5 h / 20 °C

7.1: 69 percent / Cl₂(IMes)(PCy₃)Ru=CHPh / toluene / 1 h / 75 °C

8.1: HF / pyridine; tetrahydrofuran / 0.5 h / 20 °C

With 1H-imidazole; sodium hydroxide; Cx₂BOTf; diphenyl phosphoryl azide; hydrogen fluoride; acetic acid; triethylamine; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Addition / 1.2: Condensation / 2.1: Hydrolysis / 3.1: silylation / 3.2: Hydrolysis / 4.1: Rearrangement / 4.2: Addition / 5.1: Hydrolysis / 6.1: silylation / 6.2: silylation / 7.1: Cyclization / 8.1: Ring cleavage;

DOI:10.1021/ol006560k

Reference yield:

(1R,2S)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl 4-methylpentanoate (244177-94-4) → (R)-2-{(4R,7R)-7-[(R)-1-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyl]-2,2-dimethyl-4,7-dihydro-[1,3,2]dioxasilepin-4-yl}-4-methyl-pentanethioic acid S-benzyl ester

Guidance literature:

Multi-step reaction with 7 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: imidazole / dimethylformamide / 24 h / 20 °C

3.2: H₂O / tetrahydrofuran; methanol / 4 h / 20 °C

4.1: (PhO)2PON₃; Et₃N / acetonitrile / 0.5 h / Heating

4.2: CuCl / acetonitrile / 2 h / 20 °C

5.1: AcOH / tetrahydrofuran; H₂O / 0.07 h / 55 °C

6.1: pyridine / 2 h / 20 °C

6.2: pyridine / 1.5 h / 20 °C

7.1: 69 percent / Cl₂(IMes)(PCy₃)Ru=CHPh / toluene / 1 h / 75 °C

With 1H-imidazole; sodium hydroxide; Cx₂BOTf; diphenyl phosphoryl azide; acetic acid; triethylamine; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Addition / 1.2: Condensation / 2.1: Hydrolysis / 3.1: silylation / 3.2: Hydrolysis / 4.1: Rearrangement / 4.2: Addition / 5.1: Hydrolysis / 6.1: silylation / 6.2: silylation / 7.1: Cyclization;

DOI:10.1021/ol006560k

upstream raw materials:

4-methylvaleroyl chloride

(1R,2S)-2-[N-benzyl-N-(mesitylenesulfonyl)amino]-1-phenyl-1-propanol

Downstream raw materials:

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

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

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

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