(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

Base Information

• Chemical Name: (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
• CAS No.: 281191-03-5
• Molecular Formula: C₄₄H₆₂N₂O₁₀
• Molecular Weight: 778.984
• Mol file: 281191-03-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 21 articles about (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 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: 84.0%

(2S,2'R)-2-<<3'<(tert-butoxycarbonyl)amino>-2'-methylpropanoyl>oxy>-4-methylpentanoic acid (162465-19-2) + (2R,2'E,5'S,6'R,7'E)-tert-butyl 2-[(5'-hydroxy-6'-methyl-8'-phenylocta-2',7'-dienoyl)amino]-3-(4-methoxyphenyl)propionate (281191-02-4) → (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 (281191-03-5)

Guidance literature:

(2S,2'R)-2-<<3'<(tert-butoxycarbonyl)amino>-2'-methylpropanoyl>oxy>-4-methylpentanoic acid; With 2,4,6-trichlorobenzoyl chloride; N-isopropylethylamine; In tetrahydrofuran; at 23 ℃; for 2h;

(2R,2'E,5'S,6'R,7'E)-tert-butyl 2-[(5'-hydroxy-6'-methyl-8'-phenylocta-2',7'-dienoyl)amino]-3-(4-methoxyphenyl)propionate; With dmap; In benzene; at 23 ℃; for 1h;

DOI:10.1002/ejoc.200300814

Reference yield:

(2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}-2'-methylpropinoyl)oxy]-4-methylpentanoate (245125-88-6) → (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 (281191-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / H₂ / 5 percent Pd/C / ethyl acetate / 5 h / 23 °C

2.1: 2,4,6-Cl₃C₆H₂COCl; iPrNEt / tetrahydrofuran / 2 h / 23 °C

2.2: 84 percent / DMAP / benzene / 1 h / 23 °C

With 2,4,6-trichlorobenzoyl chloride; hydrogen; N-isopropylethylamine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1002/ejoc.200300814

Reference yield:

N-α-benzyloxycarbonyl-D-tyrosine (64205-12-5) → (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 (281191-03-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 91 percent / NaOH / ethanol; H₂O / 3 h / Heating

2.1: 2,4,6-Cl₃C₆H₂COCl; iPr₂NEt / tetrahydrofuran / 0.5 h / 23 °C

2.2: 64 percent / DMAP / toluene / 3 h / 23 °C

3.1: 95 percent / H₂ / 5 percent Pd/C / methanol / 2 h

4.1: 83 percent / DMAP; EDCI / 12 h / 23 °C

5.1: 99 percent / TBAF / tetrahydrofuran / 6 h / 23 °C

6.1: 2,4,6-Cl₃C₆H₂COCl; iPrNEt / tetrahydrofuran / 2 h / 23 °C

6.2: 84 percent / DMAP / benzene / 1 h / 23 °C

With dmap; sodium hydroxide; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; hydrogen; N-isopropylethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water;

DOI:10.1002/ejoc.200300814

upstream raw materials:

(2S,2'R)-2-<<3'<(tert-butoxycarbonyl)amino>-2'-methylpropanoyl>oxy>-4-methylpentanoic acid

(2R,2'E,5'S,6'R,7'E)-tert-butyl 2-[(5'-hydroxy-6'-methyl-8'-phenylocta-2',7'-dienoyl)amino]-3-(4-methoxyphenyl)propionate

di-tert-butyl dicarbonate

trans-styrylacetic acid

Downstream raw materials:

Cryptophycin 4

(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

Refernces

• 1、 Ghosh, Arun K.,Bischoff. "Asymmetric syntheses of potent antitumor macrolides cryptophycin B and arenastatin A". . p. 2131 - 2141. Retrieved 2007/10/03.