(S)-2-Benzyloxycarbonylamino-3-(3-{4-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-methoxy-phenyl)-propionic acid

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Chemical Name:(S)-2-Benzyloxycarbonylamino-3-(3-{4-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-methoxy-phenyl)-propionic acid
CAS No.:182249-67-8
Molecular Formula:C₃₇H₄₄N₄O₁₂
Molecular Weight:736.776
Hs Code.:

(S)-2-Benzyloxycarbonylamino-3-(3-{4-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-methoxy-phenyl)-propionic acid

Synonyms:(S)-2-Benzyloxycarbonylamino-3-(3-{4-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-methoxy-phenyl)-propionic acid

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Chemical Property of (S)-2-Benzyloxycarbonylamino-3-(3-{4-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-methoxy-phenyl)-propionic acid

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Technology Process of (S)-2-Benzyloxycarbonylamino-3-(3-{4-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-methoxy-phenyl)-propionic acid

There total 17 articles about (S)-2-Benzyloxycarbonylamino-3-(3-{4-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-methoxy-phenyl)-propionic 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: 61.0%

: 182249-64-5
(S)-2-Benzyloxycarbonylamino-3-(3-{4-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-methoxy-phenyl)-propionic acid 2-iodo-ethyl ester

: 182249-67-8
(S)-2-Benzyloxycarbonylamino-3-(3-{4-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-methoxy-phenyl)-propionic acid

Guidance literature:: With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; samarium diiodide; In tetrahydrofuran; 0 deg C, 10 min; room temperature, 3 h;
DOI:10.1021/jo960956l

Reference yield:

: 1135-15-5
dihydroisoferulic acid

: 182249-67-8
(S)-2-Benzyloxycarbonylamino-3-(3-{4-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-methoxy-phenyl)-propionic acid

Guidance literature:: Multi-step reaction with 13 steps

1: 65 percent / DBU / benzene / 7 h / Heating

2: 86 percent / DMAP, Et₃N / CH₂Cl₂ / 17 h / Ambient temperature

3: 99 percent / H₂ / Pd-C / tetrahydrofuran / 3.5 h / 760 Torr / Ambient temperature

5: 1) KHMDS, 2) trisyl azide / 1) THF, toluene, -78 deg C, 20 min, 2) THF, toluene, -78 deg C, 5 min

6: 62 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

7: 374 mg / aq. H₂O₂, LiOH / tetrahydrofuran / 1.5 h / 0 °C

8: DMAP, DCC / CH₂Cl₂ / 12 h / 0 - 20 °C

9: H₂, 5 N HCl / Pd-C / tetrahydrofuran; methanol / 1.5 h / 760 Torr / Ambient temperature

10: NaHCO₃ / CH₂Cl₂; H₂O / 0 deg C, 1.5 h, room temperature, 2 h

12: 98 percent / NaI / acetone / 6 h / Heating

13: 61 percent / DMPU, SmI₂ / tetrahydrofuran / 0 deg C, 10 min; room temperature, 3 h

With hydrogenchloride; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; samarium diiodide; 2,4,6-Triisopropylbenzenesulfonyl azide; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone; benzene;
DOI:10.1021/jo960956l

Reference yield:

: 159750-04-6
(S)-2-Azido-3-(4-chlorophenyl)propionic acid

: 182249-67-8
(S)-2-Benzyloxycarbonylamino-3-(3-{4-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-methoxy-phenyl)-propionic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / p-TsOH / 8 h / Heating

2: H₂, 5 N HCl / Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature

3: HOBt*H₂O, i-Pr₂NEt, EDC / tetrahydrofuran; dimethylformamide / 24 h / 0 - 20 °C

5: 98 percent / NaI / acetone / 6 h / Heating

6: 61 percent / DMPU, SmI₂ / tetrahydrofuran / 0 deg C, 10 min; room temperature, 3 h

With hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; samarium diiodide; hydrogen; benzotriazol-1-ol; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo960956l