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Cas Database

450407-04-2

450407-04-2

Identification

  • Product Name:Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe

  • CAS Number: 450407-04-2

  • EINECS:

  • Molecular Weight:749.905

  • Molecular Formula: C40H55N5O9

  • HS Code:

  • Mol File:450407-04-2.mol

Synonyms:Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe

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Relevant articles and documentsAll total 2 Articles be found

A rapid and efficient synthesis of β-casomorphin employing Boc-amino acids and 9-fluorenylmethyl chloroformate as a coupling agent

Babu, V.V. Suresh,Tantry

, p. 2708 - 2712 (2007/10/03)

The synthesis of β-casomorphin H-Tyr-Pro-Phe-Pro-Gly-OH employing Boc group for Nα-protection and 9-fluorenylmethyl chloroformate (Fmoc-Cl) for the formation of peptide bond is described. The protocol employing Fmoc-Cl as coupling reagent is found to be simple, efficient and rapid. All the intermediate peptides as well as the final protected peptide Boc-Tyr( iBu)-Pro-Phe-Pro-Gly-OMe have been isolated and fully characterized. They have been obtained in good yield and with high purity.

Coupling in the absence of a tertiary base: A method for the deprotonation of hydrochloride salts of peptide esters to free amino peptide esters

Tantry, Subramanyam J.,Ananda,Suresh Babu

, p. 1028 - 1031 (2007/10/03)

The deprotonation of hydrochloride salts of peptide esters is accomplished using activated zinc dust. The reaction is neat and quantitative. Addition of a tertiary base is eliminated during the coupling. The free amino peptide esters have been isolated in good yield and purity. This method is extended for the synthesis of β-casomorphin (Tyr-Pro-Phe-Pro-Gly). During its synthesis, all the intermediate free amino peptide esters have been isolated and characterized.

Process route upstream and downstream products

Process route

Boc-Tyr(t-Bu)-OH
47375-34-8

Boc-Tyr(t-Bu)-OH

H-Pro-Phe-Pro-Gly-OMe
77434-42-5

H-Pro-Phe-Pro-Gly-OMe

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe
450407-04-2

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe

Conditions
Conditions Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; cooling;
84%
With 4-methyl-morpholine; (fluorenylmethoxy)carbonyl chloride; In tetrahydrofuran; at -15 ℃; for 0.5h;
84%
H-Pro-Gly-OMe
33256-35-8

H-Pro-Gly-OMe

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe
450407-04-2

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: 87 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
2.1: HCl / ethyl acetate; H2O / 0.5 h
2.2: 81 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
3.1: 80 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
4.1: HCl / ethyl acetate; H2O / 0.5 h
4.2: 80 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
5.1: 84 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
With 4-methyl-morpholine; hydrogenchloride; (fluorenylmethoxy)carbonyl chloride; In tetrahydrofuran; water; ethyl acetate;
Multi-step reaction with 5 steps
1: 87 percent / DCC; HOBt / tetrahydrofuran / cooling
2: 81 percent / HCl / ethyl acetate / 0.5 h
3: 80 percent / DCC; HOBt / tetrahydrofuran / cooling
4: 80 percent / HCl / ethyl acetate / 0.5 h
5: 84 percent / DCC; HOBt / tetrahydrofuran / cooling
With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate;
tert-butyloxycarbonyl-prolyl-glycine methyl ester
34290-72-7,92132-25-7,1097194-13-2

tert-butyloxycarbonyl-prolyl-glycine methyl ester

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe
450407-04-2

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: HCl / ethyl acetate; H2O / 0.5 h
1.2: 86 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
2.1: 87 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
3.1: HCl / ethyl acetate; H2O / 0.5 h
3.2: 81 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
4.1: 80 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
5.1: HCl / ethyl acetate; H2O / 0.5 h
5.2: 80 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
6.1: 84 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
With 4-methyl-morpholine; hydrogenchloride; (fluorenylmethoxy)carbonyl chloride; In tetrahydrofuran; water; ethyl acetate;
Multi-step reaction with 6 steps
1: 86 percent / HCl / ethyl acetate / 0.5 h
2: 87 percent / DCC; HOBt / tetrahydrofuran / cooling
3: 81 percent / HCl / ethyl acetate / 0.5 h
4: 80 percent / DCC; HOBt / tetrahydrofuran / cooling
5: 80 percent / HCl / ethyl acetate / 0.5 h
6: 84 percent / DCC; HOBt / tetrahydrofuran / cooling
With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate;
N<sup>α</sup>-Boc-L-phenylalanyl-L-prolyl-glycine methyl ester
100008-17-1

Nα-Boc-L-phenylalanyl-L-prolyl-glycine methyl ester

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe
450407-04-2

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: HCl / ethyl acetate; H2O / 0.5 h
1.2: 81 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
2.1: 80 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
3.1: HCl / ethyl acetate; H2O / 0.5 h
3.2: 80 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
4.1: 84 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
With 4-methyl-morpholine; hydrogenchloride; (fluorenylmethoxy)carbonyl chloride; In tetrahydrofuran; water; ethyl acetate;
Multi-step reaction with 4 steps
1: 81 percent / HCl / ethyl acetate / 0.5 h
2: 80 percent / DCC; HOBt / tetrahydrofuran / cooling
3: 80 percent / HCl / ethyl acetate / 0.5 h
4: 84 percent / DCC; HOBt / tetrahydrofuran / cooling
With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate;
N<sup>α</sup>-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester
100008-18-2

Nα-Boc-L-Prolyl-L-phenylalanyl-L-prolyl-glycine methyl ester

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe
450407-04-2

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: HCl / ethyl acetate; H2O / 0.5 h
1.2: 80 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
2.1: 84 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
With 4-methyl-morpholine; hydrogenchloride; (fluorenylmethoxy)carbonyl chloride; In tetrahydrofuran; water; ethyl acetate;
Multi-step reaction with 2 steps
1: 80 percent / HCl / ethyl acetate / 0.5 h
2: 84 percent / DCC; HOBt / tetrahydrofuran / cooling
With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate;
H-Phe-Pro-Gly-OMe
77434-41-4

H-Phe-Pro-Gly-OMe

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe
450407-04-2

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: 80 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
2.1: HCl / ethyl acetate; H2O / 0.5 h
2.2: 80 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
3.1: 84 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
With 4-methyl-morpholine; hydrogenchloride; (fluorenylmethoxy)carbonyl chloride; In tetrahydrofuran; water; ethyl acetate;
Multi-step reaction with 3 steps
1: 80 percent / DCC; HOBt / tetrahydrofuran / cooling
2: 80 percent / HCl / ethyl acetate / 0.5 h
3: 84 percent / DCC; HOBt / tetrahydrofuran / cooling
With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate;
1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe
450407-04-2

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1.1: 90 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
2.1: HCl / ethyl acetate; H2O / 0.5 h
2.2: 86 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
3.1: 87 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
4.1: HCl / ethyl acetate; H2O / 0.5 h
4.2: 81 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
5.1: 80 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
6.1: HCl / ethyl acetate; H2O / 0.5 h
6.2: 80 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
7.1: 84 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
With 4-methyl-morpholine; hydrogenchloride; (fluorenylmethoxy)carbonyl chloride; In tetrahydrofuran; water; ethyl acetate;
1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe
450407-04-2

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: 90 percent / DCC; HOBt / tetrahydrofuran / cooling
2: 86 percent / HCl / ethyl acetate / 0.5 h
3: 87 percent / DCC; HOBt / tetrahydrofuran / cooling
4: 81 percent / HCl / ethyl acetate / 0.5 h
5: 80 percent / DCC; HOBt / tetrahydrofuran / cooling
6: 80 percent / HCl / ethyl acetate / 0.5 h
7: 84 percent / DCC; HOBt / tetrahydrofuran / cooling
With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate;
Boc-Tyr(t-Bu)-OH
47375-34-8

Boc-Tyr(t-Bu)-OH

H-Pro-Phe-Pro-Gly-OMe
77434-42-5

H-Pro-Phe-Pro-Gly-OMe

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe
450407-04-2

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe

Conditions
Conditions Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; cooling;
84%
With 4-methyl-morpholine; (fluorenylmethoxy)carbonyl chloride; In tetrahydrofuran; at -15 ℃; for 0.5h;
84%
H-Pro-Gly-OMe
33256-35-8

H-Pro-Gly-OMe

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe
450407-04-2

Boc-Tyr(t-Bu)-Pro-Phe-Pro-Gly-OMe

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: 87 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
2.1: HCl / ethyl acetate; H2O / 0.5 h
2.2: 81 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
3.1: 80 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
4.1: HCl / ethyl acetate; H2O / 0.5 h
4.2: 80 percent / Zn dust / tetrahydrofuran / 0.17 h / 20 °C
5.1: 84 percent / Fmoc-Cl; NMM / tetrahydrofuran / 0.5 h / -15 °C
With 4-methyl-morpholine; hydrogenchloride; (fluorenylmethoxy)carbonyl chloride; In tetrahydrofuran; water; ethyl acetate;
Multi-step reaction with 5 steps
1: 87 percent / DCC; HOBt / tetrahydrofuran / cooling
2: 81 percent / HCl / ethyl acetate / 0.5 h
3: 80 percent / DCC; HOBt / tetrahydrofuran / cooling
4: 80 percent / HCl / ethyl acetate / 0.5 h
5: 84 percent / DCC; HOBt / tetrahydrofuran / cooling
With hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate;

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