2-(3-tert-butoxycarbonylamino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid 4-[2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-1-(2,3-dihydroxy-1-methyl-3-phenyl-propyl)-but-3-enyl ester

Base Information

Chemical Name:2-(3-tert-butoxycarbonylamino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid 4-[2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-1-(2,3-dihydroxy-1-methyl-3-phenyl-propyl)-but-3-enyl ester
CAS No.:270901-33-2
Molecular Formula:C₄₃H₅₈Cl₄N₂O₁₂
Molecular Weight:936.752
Hs Code.:

2-(3-<i>tert</i>-butoxycarbonylamino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid 4-[2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-1-(2,3-dihydroxy-1-methyl-3-phenyl-propyl)-but-3-enyl ester

Synonyms:2-(3-tert-butoxycarbonylamino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid 4-[2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-1-(2,3-dihydroxy-1-methyl-3-phenyl-propyl)-but-3-enyl ester

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Chemical Property of 2-(3-tert-butoxycarbonylamino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid 4-[2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-1-(2,3-dihydroxy-1-methyl-3-phenyl-propyl)-but-3-enyl ester

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Technology Process of 2-(3-tert-butoxycarbonylamino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid 4-[2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-1-(2,3-dihydroxy-1-methyl-3-phenyl-propyl)-but-3-enyl ester

There total 1 articles about 2-(3-tert-butoxycarbonylamino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid 4-[2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-1-(2,3-dihydroxy-1-methyl-3-phenyl-propyl)-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: 61.0%

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

: 2-(3-tert-butoxycarbonylamino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid 4-[2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-1-(2,3-dihydroxy-1-methyl-3-phenyl-propyl)-but-3-enyl ester

: 270901-33-2
2-(3-tert-butoxycarbonylamino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid 4-[2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-1-(2,3-dihydroxy-1-methyl-3-phenyl-propyl)-but-3-enyl ester

Guidance literature:: With methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium dioxotetrahydroxoosmate(VI); potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 20 ℃; for 20.5h;
DOI:10.1021/jo9919862

Reference yield:

: 270901-33-2
2-(3-tert-butoxycarbonylamino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid 4-[2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-1-(2,3-dihydroxy-1-methyl-3-phenyl-propyl)-but-3-enyl ester

: cryptophycin 52

Guidance literature:: Multi-step reaction with 5 steps

1: TFA / CH₂Cl₂ / 1.5 h

2: 2-hydroxypyridine / acetonitrile; toluene / 21 h / 40 °C

3: 153 mg / PPTS / CH₂Cl₂ / 2.5 h / 20 °C

4: 85 percent / acetyl bromide / CH₂Cl₂ / 2.33 h / 20 °C

5: 94 percent / K₂CO₃ / tetrahydrofuran; methanol / 6 h / 0 °C

With 2-hydroxypyridin; Acetyl bromide; pyridinium p-toluenesulfonate; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; 1: Hydrolysis / 2: Cyclization / 3: acetalization / 4: Ring cleavage / 5: Cyclization;
DOI:10.1021/jo9919862