(S)-2-Hydroxy-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(4-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester

Base Information

• Chemical Name: (S)-2-Hydroxy-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(4-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester
• CAS No.: 1026176-43-1
• Molecular Formula: C₃₆H₅₁NO₇Si
• Molecular Weight: 637.889
• Mol file: 1026176-43-1.mol

Synonyms:

Chemical Property of (S)-2-Hydroxy-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(4-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Hydroxy-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(4-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester

There total 12 articles about (S)-2-Hydroxy-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(4-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl 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:

(S)-2-(4-Methoxy-benzyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(4-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester (172225-78-4) → (S)-2-Hydroxy-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(4-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester (1026176-43-1)

Guidance literature:

With boron trifluoride diethyl etherate; thiophenol; at -50 ℃;

DOI:10.1248/cpb.43.1598

Reference yield:

(E)-(3S,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-6-phenyl-hex-5-en-3-ol (162473-70-3) → (S)-2-Hydroxy-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(4-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester (1026176-43-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / Et₃N, DMAP / CH₂Cl₂

2: n-Bu₄NF, AcOH

3: Dess-Martin periodinate

4: NaH / dimethylformamide

5: PhSH, BF₃*OEt₂ / -50 °C

With dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; Dess-Martin periodane; acetic acid; thiophenol; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.43.1598

Reference yield:

(S)-2-(4-Methoxy-benzyloxy)-4-methyl-pentanoyl chloride (162473-74-7) → (S)-2-Hydroxy-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(4-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester (1026176-43-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / Et₃N, DMAP / CH₂Cl₂

2: n-Bu₄NF, AcOH

3: Dess-Martin periodinate

4: NaH / dimethylformamide

5: PhSH, BF₃*OEt₂ / -50 °C

With dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; Dess-Martin periodane; acetic acid; thiophenol; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.43.1598

upstream raw materials:

(S)-2-(4-Methoxy-benzyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(4-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester

(S)-2-(4-Methoxy-benzyloxy)-4-methyl-pentanoyl chloride

(E)-(3S,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-6-phenyl-hex-5-en-3-ol

(S)-2-(4-Methoxy-benzyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-4-phenyl-but-3-enyl ester

Downstream raw materials:

desepoxyarenastatin A

(S)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(4-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester