(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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Chemical Name:(R)-1-{(S)-2-[2-((2S,9R)-2-Amino-9-hydroxy-8-oxo-decanoylamino)-2-methyl-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid
CAS No.:874384-22-2
Molecular Formula:C₂₈H₄₂N₄O₇
Molecular Weight:546.664
Hs Code.:

Synonyms:(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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Chemical Property of (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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Technology Process of (R)-1-{(S)-2-[2-((2S,9R)-2-Amino-9-hydroxy-8-oxo-decanoylamino)-2-methyl-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid

There total 12 articles about (R)-1-{(S)-2-[2-((2S,9R)-2-Amino-9-hydroxy-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: 60.0%

: 874384-21-1
(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

: 874384-22-2
(R)-1-{(S)-2-[2-((2S,9R)-2-Amino-9-hydroxy-8-oxo-decanoylamino)-2-methyl-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid

Guidance literature:: With chlorotriisopropylsilane; water; trifluoroacetic acid; for 0.333333h;
DOI:10.1021/jo0518250

Reference yield:

: 850209-98-2
(S)-2-dibenzylamino-5-hydroxypentanoic acid benzyl ester

: 874384-22-2
(R)-1-{(S)-2-[2-((2S,9R)-2-Amino-9-hydroxy-8-oxo-decanoylamino)-2-methyl-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 7 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

6.1: 60 percent / trifluoroacetic acid; H₂O; triisopropyl silane / 0.33 h

With hydrogenchloride; oxalyl dichloride; chlorotriisopropylsilane; water; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 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:

: 874384-01-7
benzyl (S)-2-(dibenzylamino)pent-4-enoate

: 874384-22-2
(R)-1-{(S)-2-[2-((2S,9R)-2-Amino-9-hydroxy-8-oxo-decanoylamino)-2-methyl-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1: xantphos; H₂ / HRh(CO)(PPh₃)3 / toluene / 96 h / 40 °C / 15200 Torr

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

3: 75 percent / H₂ / Pd(OH)2/C / methanol / 12 h / 20 °C / 4560 Torr

4: 60 percent / trifluoroacetic acid; H₂O; triisopropyl silane / 0.33 h

With chlorotriisopropylsilane; water; hydrogen; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trifluoroacetic acid; lithium chloride; carbonylhydridetris(triphenylphosphine)rhodium(I); palladium dihydroxide; In methanol; toluene; acetonitrile; 2: Wittig-Horner-Emmons reaction;
DOI:10.1021/jo0518250