(4S,5R)-4-(3-Benzyloxycarbonylamino-propyl)-5-((R)-1-{(E)-(S)-1-[4-(2,6-dichloro-benzyloxy)-benzyl]-3-methoxycarbonyl-allylcarbamoyl}-2-phenyl-ethylcarbamoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4S,5R)-4-(3-Benzyloxycarbonylamino-propyl)-5-((R)-1-{(E)-(S)-1-[4-(2,6-dichloro-benzyloxy)-benzyl]-3-methoxycarbonyl-allylcarbamoyl}-2-phenyl-ethylcarbamoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 176755-27-4
• Molecular Formula: C₅₀H₅₈Cl₂N₄O₁₀
• Molecular Weight: 945.937

Synonyms:(4S,5R)-4-(3-Benzyloxycarbonylamino-propyl)-5-((R)-1-{(E)-(S)-1-[4-(2,6-dichloro-benzyloxy)-benzyl]-3-methoxycarbonyl-allylcarbamoyl}-2-phenyl-ethylcarbamoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (4S,5R)-4-(3-Benzyloxycarbonylamino-propyl)-5-((R)-1-{(E)-(S)-1-[4-(2,6-dichloro-benzyloxy)-benzyl]-3-methoxycarbonyl-allylcarbamoyl}-2-phenyl-ethylcarbamoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (4S,5R)-4-(3-Benzyloxycarbonylamino-propyl)-5-((R)-1-{(E)-(S)-1-[4-(2,6-dichloro-benzyloxy)-benzyl]-3-methoxycarbonyl-allylcarbamoyl}-2-phenyl-ethylcarbamoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 6 articles about (4S,5R)-4-(3-Benzyloxycarbonylamino-propyl)-5-((R)-1-{(E)-(S)-1-[4-(2,6-dichloro-benzyloxy)-benzyl]-3-methoxycarbonyl-allylcarbamoyl}-2-phenyl-ethylcarbamoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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: 75.0%

(4S,5R)-4-(3-Benzyloxycarbonylamino-propyl)-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester (176755-30-9) + (E)-(S)-4-((R)-2-Amino-3-phenyl-propionylamino)-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester (420118-92-9) → (4S,5R)-4-(3-Benzyloxycarbonylamino-propyl)-5-((R)-1-{(E)-(S)-1-[4-(2,6-dichloro-benzyloxy)-benzyl]-3-methoxycarbonyl-allylcarbamoyl}-2-phenyl-ethylcarbamoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (176755-27-4)

Guidance literature:

With triethylamine; diethyl dicarbonate; In N,N-dimethyl-formamide; at 0 ℃; for 4.5h;

DOI:10.1016/0040-4039(96)00270-5

Reference yield:

benzyl tert-butyl (5-(methoxy(methyl)amino)-5-oxopentane-1,4-diyl) (S)-dicarbamate → (4S,5R)-4-(3-Benzyloxycarbonylamino-propyl)-5-((R)-1-{(E)-(S)-1-[4-(2,6-dichloro-benzyloxy)-benzyl]-3-methoxycarbonyl-allylcarbamoyl}-2-phenyl-ethylcarbamoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (176755-27-4)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran / 0.58 h / -78 °C

2: K-selectride / tetrahydrofuran / 0.5 h / -78 °C

3: 61 percent / pyridine*p-TsOH / CH₂Cl₂ / 60 h / Ambient temperature

4: 59 percent / NaIO₄, RuCl₃ / acetonitrile; ethyl acetate; H₂O / 1.5 h / Ambient temperature

5: 75 percent / DEPC, Et₃N / dimethylformamide / 4.5 h / 0 °C

With ruthenium trichloride; sodium periodate; pyridinium p-toluenesulfonate; potassium tri-sec-butyl-borohydride; triethylamine; diethyl dicarbonate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(96)00270-5

Reference yield:

((S)-4-tert-Butoxycarbonylamino-5-furan-2-yl-5-hydroxy-pentyl)-carbamic acid benzyl ester → (4S,5R)-4-(3-Benzyloxycarbonylamino-propyl)-5-((R)-1-{(E)-(S)-1-[4-(2,6-dichloro-benzyloxy)-benzyl]-3-methoxycarbonyl-allylcarbamoyl}-2-phenyl-ethylcarbamoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (176755-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / pyridine*p-TsOH / CH₂Cl₂ / 60 h / Ambient temperature

2: 59 percent / NaIO₄, RuCl₃ / acetonitrile; ethyl acetate; H₂O / 1.5 h / Ambient temperature

3: 75 percent / DEPC, Et₃N / dimethylformamide / 4.5 h / 0 °C

With ruthenium trichloride; sodium periodate; pyridinium p-toluenesulfonate; triethylamine; diethyl dicarbonate; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(96)00270-5

upstream raw materials:

(4S,5R)-4-(3-Benzyloxycarbonylamino-propyl)-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester

(E)-(S)-4-((R)-2-Amino-3-phenyl-propionylamino)-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester

(4S,5R)-4-(3-Benzyloxycarbonylamino-propyl)-5-furan-2-yl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(E)-(S)-4-((R)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester

Downstream raw materials:

cyclotheonamide B

C₅₁H₅₇Cl₂N₇O₁₀

C₅₄H₆₉Cl₂N₉O₁₂

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