(R)-1-((S)-2-{2-[(2S,9R)-2-tert-Butoxycarbonylamino-9-(tert-butyl-dimethyl-silanyloxy)-8-oxo-decanoylamino]-2-methyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (R)-1-((S)-2-{2-[(2S,9R)-2-tert-Butoxycarbonylamino-9-(tert-butyl-dimethyl-silanyloxy)-8-oxo-decanoylamino]-2-methyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid
• CAS No.: 874384-21-1
• Molecular Formula: C₃₉H₆₄N₄O₉Si
• Molecular Weight: 761.044

Synonyms:(R)-1-((S)-2-{2-[(2S,9R)-2-tert-Butoxycarbonylamino-9-(tert-butyl-dimethyl-silanyloxy)-8-oxo-decanoylamino]-2-methyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid

Chemical Property of (R)-1-((S)-2-{2-[(2S,9R)-2-tert-Butoxycarbonylamino-9-(tert-butyl-dimethyl-silanyloxy)-8-oxo-decanoylamino]-2-methyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid

Chemical Property:

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Technology Process of (R)-1-((S)-2-{2-[(2S,9R)-2-tert-Butoxycarbonylamino-9-(tert-butyl-dimethyl-silanyloxy)-8-oxo-decanoylamino]-2-methyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid

There total 11 articles about (R)-1-((S)-2-{2-[(2S,9R)-2-tert-Butoxycarbonylamino-9-(tert-butyl-dimethyl-silanyloxy)-8-oxo-decanoylamino]-2-methyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid 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:

(2S,9R)-2-(tert-butoxycarbonylamino)-9-(tert-butyldimethylsilyloxy)-8-oxo-6-decanoic acid (874384-12-0) + N-Fmoc L-Phe (35661-40-6) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-α-aminoisobutyric acid (94744-50-0) + (R)-Pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (71989-31-6,109425-54-9,144829-96-9,101555-62-8) → (R)-1-((S)-2-{2-[(2S,9R)-2-tert-Butoxycarbonylamino-9-(tert-butyl-dimethyl-silanyloxy)-8-oxo-decanoylamino]-2-methyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid (874384-21-1)

Guidance literature:

Multistep reaction;

DOI:10.1021/jo0518250

Reference yield:

(S)-2-dibenzylamino-5-hydroxypentanoic acid benzyl ester (850209-98-2) → (R)-1-((S)-2-{2-[(2S,9R)-2-tert-Butoxycarbonylamino-9-(tert-butyl-dimethyl-silanyloxy)-8-oxo-decanoylamino]-2-methyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid (874384-21-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

2.1: LiN(SiMe₃)2 / tetrahydrofuran / 0 °C

2.2: tetrahydrofuran / 12 h / 20 °C

3.1: 94 percent / HCl / ethyl acetate / 0.33 h / 20 °C

4.1: LiCl; ethyldiisopropylamine / acetonitrile / 72 h / 20 °C

5.1: 75 percent / H₂ / Pd(OH)2/C / methanol / 12 h / 20 °C / 4560 Torr

With hydrogenchloride; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile; 1.1: Swern oxidation / 4.1: Wittig-Horner-Emmons reaction;

DOI:10.1021/jo0518250

Reference yield:

(R)-dimethyl (3-((tert-butyldimethylsilyl)oxy)-2-oxobutyl)phosphonate (874384-04-0) → (R)-1-((S)-2-{2-[(2S,9R)-2-tert-Butoxycarbonylamino-9-(tert-butyl-dimethyl-silanyloxy)-8-oxo-decanoylamino]-2-methyl-propionylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid (874384-21-1)

Guidance literature:

Multi-step reaction with 3 steps

1: LiCl; ethyldiisopropylamine / acetonitrile / 72 h / 20 °C

2: 75 percent / H₂ / Pd(OH)2/C / methanol / 12 h / 20 °C / 4560 Torr

With hydrogen; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium dihydroxide; In methanol; acetonitrile; 1: Wittig-Horner-Emmons reaction;

DOI:10.1021/jo0518250

upstream raw materials:

(2S,9R)-2-(tert-butoxycarbonylamino)-9-(tert-butyldimethylsilyloxy)-8-oxo-6-decanoic acid

N-Fmoc L-Phe

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-α-aminoisobutyric acid

(R)-Pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester

Downstream raw materials:

(-)-(3S,9S,14aR)-9-benzyl-3-[(R)-7-hydroxy-6-oxooctyl]-6,6-dimethyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone

(R)-1-{(S)-2-[2-((2S,9R)-2-Amino-9-hydroxy-8-oxo-decanoylamino)-2-methyl-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid

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