D-Phenylalanine, N-[(2S,3R,5Z)-9-amino-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-meth yl-1,9-dioxo-5-nonen-1-yl]-D-valyl-D-alanyl-, 1,1-dimethylethyl ester

Base Information

Chemical Name:D-Phenylalanine, N-[(2S,3R,5Z)-9-amino-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-meth yl-1,9-dioxo-5-nonen-1-yl]-D-valyl-D-alanyl-, 1,1-dimethylethyl ester
CAS No.:922493-52-5
Molecular Formula:C36H57N5O8
Molecular Weight:687.877
Hs Code.:

D-Phenylalanine,
N-[(2S,3R,5Z)-9-amino-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-meth
yl-1,9-dioxo-5-nonen-1-yl]-D-valyl-D-alanyl-, 1,1-dimethylethyl ester

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Chemical Property of D-Phenylalanine, N-[(2S,3R,5Z)-9-amino-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-meth yl-1,9-dioxo-5-nonen-1-yl]-D-valyl-D-alanyl-, 1,1-dimethylethyl ester

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Technology Process of D-Phenylalanine, N-[(2S,3R,5Z)-9-amino-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-meth yl-1,9-dioxo-5-nonen-1-yl]-D-valyl-D-alanyl-, 1,1-dimethylethyl ester

There total 18 articles about D-Phenylalanine, N-[(2S,3R,5Z)-9-amino-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-meth yl-1,9-dioxo-5-nonen-1-yl]-D-valyl-D-alanyl-, 1,1-dimethylethyl 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%

: 922493-49-0
(Z)-(2S,3R)-3-[(tert-butyloxycarbonyl)amino]-2-methyl-5-nonenedioic acid 9-amide

: 922493-51-4
C₂₁H₃₃N₃O₄

: 922493-52-5
C₃₆H₅₇N₅O₈

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 16h;
DOI:10.1002/anie.200602033

Reference yield:

: C₁₅H₂₀O₄

: 922493-52-5
C₃₆H₅₇N₅O₈

Guidance literature:: Multi-step reaction with 14 steps

1.1: NaBH₄ / ethanol / 0.5 h

1.2: 382 mg / K₂CO₃ / methanol / 24 h / 20 °C

2.1: 90 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

3.1: triethylamine / tetrahydrofuran / 20 °C

4.1: 1.96 g / NaN₃ / dimethylformamide / 5 h / 60 °C

5.1: H₂ / PtO₂ / ethyl acetate

6.1: 2.66 g / triethylamine / CH₂Cl₂ / 20 °C

7.1: 100 percent / H₂ / Pd on carbon / ethanol

8.1: 93 percent / oxalyl chloride; methyl sulfoxide; Et₃N / CH₂Cl₂ / 1.42 h / -78 - 20 °C

9.1: potassium hexamethyldisilylamide / tetrahydrofuran / 1 h / -78 °C / cooling

9.2: 76 percent / tetrahydrofuran / -78 - 20 °C

10.1: 91 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 6.5 h / 70 °C

11.1: 79 percent / triethylamine; NH₄Cl; diphenylphosphorylazide / dimethylformamide / -16 °C

12.1: 60 percent / pyridine; HF / 3 h

13.1: 37 percent / 2,2,6,6-tetramethyl-1-piperidinyloxy; NaClO₂; NaClO / acetonitrile; aq. phosphate buffer / 35 °C / pH 6.85

14.1: 61 percent / diisopropylethylamine; 1-hydroxybenzotriazole; 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride / CH₂Cl₂ / 16 h / 0 - 20 °C

With pyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hypochlorite; sodium chlorite; sodium tetrahydroborate; sodium azide; oxalyl dichloride; diphenylphosphoranyl azide; hydrogen fluoride; hydrogen; potassium hexamethylsilazane; ammonium chloride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; phosphate buffer; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 8.1: Swern oxidation / 9.1: Wittig olefination;
DOI:10.1002/anie.200602033

Reference yield:

: 922493-41-2
C₂₉H₃₇O₂SiN₃

: 922493-52-5
C₃₆H₅₇N₅O₈

Guidance literature:: Multi-step reaction with 10 steps

1.1: H₂ / PtO₂ / ethyl acetate

2.1: 2.66 g / triethylamine / CH₂Cl₂ / 20 °C

3.1: 100 percent / H₂ / Pd on carbon / ethanol

4.1: 93 percent / oxalyl chloride; methyl sulfoxide; Et₃N / CH₂Cl₂ / 1.42 h / -78 - 20 °C

5.1: potassium hexamethyldisilylamide / tetrahydrofuran / 1 h / -78 °C / cooling

5.2: 76 percent / tetrahydrofuran / -78 - 20 °C

6.1: 91 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 6.5 h / 70 °C

7.1: 79 percent / triethylamine; NH₄Cl; diphenylphosphorylazide / dimethylformamide / -16 °C

8.1: 60 percent / pyridine; HF / 3 h

9.1: 37 percent / 2,2,6,6-tetramethyl-1-piperidinyloxy; NaClO₂; NaClO / acetonitrile; aq. phosphate buffer / 35 °C / pH 6.85

10.1: 61 percent / diisopropylethylamine; 1-hydroxybenzotriazole; 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride / CH₂Cl₂ / 16 h / 0 - 20 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hypochlorite; sodium chlorite; oxalyl dichloride; diphenylphosphoranyl azide; hydrogen fluoride; hydrogen; potassium hexamethylsilazane; ammonium chloride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; phosphate buffer; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 4.1: Swern oxidation / 5.1: Wittig olefination;
DOI:10.1002/anie.200602033