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

Base Information

• Chemical Name: (S)-2-((R)-3-Amino-2-methyl-propionyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-1-carboxy-2-(4-methoxy-phenyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester
• CAS No.: 162465-18-1
• Molecular Formula: C₃₅H₄₆N₂O₈
• Molecular Weight: 622.759
• Mol file: 162465-18-1.mol

Synonyms:(S)-2-((R)-3-Amino-2-methyl-propionyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-1-carboxy-2-(4-methoxy-phenyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester

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

There total 20 articles about (S)-2-((R)-3-Amino-2-methyl-propionyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-1-carboxy-2-(4-methoxy-phenyl)-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:

N-α-benzyloxycarbonyl-D-tyrosine (64205-12-5) → (S)-2-((R)-3-Amino-2-methyl-propionyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-1-carboxy-2-(4-methoxy-phenyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester (162465-18-1)

Guidance literature:

Multi-step reaction with 7 steps

1: aq. NaOH / ethanol / Heating

2: DMAP; 2,4,6-trichlorobenzoyl chloride; iPr₂NEt

3: H₂ / Pd-C / methanol

4: 79 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 23 °C

5: 99 percent / TBAF; H₂O / tetrahydrofuran / 23 °C

6: 84 percent / 2,4,6-trichlorobenzoyl chloride; iPr₂NEt; DMAP / 23 °C

7: CF₃COOH / 2 h / 23 °C

With dmap; sodium hydroxide; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; water; hydrogen; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1: Methylation / 2: Esterification / 3: Hydrogenation / 4: Acylation / 5: desilylation / 6: Esterification / 7: Substitution;

DOI:10.1021/ol000058i

Reference yield:

(R)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionic acid (65806-89-5) → (S)-2-((R)-3-Amino-2-methyl-propionyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-1-carboxy-2-(4-methoxy-phenyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester (162465-18-1)

Guidance literature:

Multi-step reaction with 6 steps

1: DMAP; 2,4,6-trichlorobenzoyl chloride; iPr₂NEt

2: H₂ / Pd-C / methanol

3: 79 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 23 °C

4: 99 percent / TBAF; H₂O / tetrahydrofuran / 23 °C

5: 84 percent / 2,4,6-trichlorobenzoyl chloride; iPr₂NEt; DMAP / 23 °C

6: CF₃COOH / 2 h / 23 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; water; hydrogen; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 1: Esterification / 2: Hydrogenation / 3: Acylation / 4: desilylation / 5: Esterification / 6: Substitution;

DOI:10.1021/ol000058i

Reference yield:

(2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}-2'-methylpropinoyl)oxy]-4-methylpentanoate (245125-88-6) → (S)-2-((R)-3-Amino-2-methyl-propionyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-1-carboxy-2-(4-methoxy-phenyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester (162465-18-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / H₂ / Pd/C / ethyl acetate / 5 h

2: 84 percent / 2,4,6-trichlorobenzoyl chloride; iPr₂NEt; DMAP / 23 °C

3: CF₃COOH / 2 h / 23 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; hydrogen; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In ethyl acetate; 1: Hydrogenation / 2: Esterification / 3: Substitution;

DOI:10.1021/ol000058i

upstream raw materials:

(2S,2'R,1''S,2''R,1''''R)1''-(3'''-{1''''-[(tert-butoxy)carbonyl]-2''''-p-methoxyphenylethylcarbamoyl}allyl)-2''-methyl-4''-phenylbut-3''-enyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}-2'-methylpropionyl)oxy]-4-methylpentanoate

trans-styrylacetic acid

N-α-benzyloxycarbonyl-D-tyrosine

(R)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionic acid

Downstream raw materials:

Cryptophycin 4

Refernces

• 1、 Barrow, Russell A.,Hemscheidt, Thomas,Liang, Jian,Paik, Seunguk,Moore, Richard E.,Tius, Marcus A.. "Total synthesis of cryptophycins. Revision of the structures of cryptophycins A and C". . p. 2479 - 2490. Retrieved 2007/10/02.