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Cas Database

1294518-17-4

1294518-17-4

Identification

  • Product Name:(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine

  • CAS Number: 1294518-17-4

  • EINECS:

  • Molecular Weight:394.448

  • Molecular Formula: C18H22N2O6S

  • HS Code:

  • Mol File:1294518-17-4.mol

Synonyms:(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine

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Relevant articles and documentsAll total 2 Articles be found

Synthesis of protected 2-pyrrolylalanine for peptide chemistry and examination of its influence on prolyl amide isomer equilibrium

Doerr, Aurelie A.,Lubell, William D.

, p. 6414 - 6422 (2012/10/08)

Protected enantiopure 2-pyrrolylalanine was synthesized for application in peptide science as an electron-rich arylalanine (histidine) analog with π-donor capability. (2S)-N-(Boc)-N′-(Phenylsulfonyl)-, (2S)-N,N′-bis-(phenylsulfonyl)-, and (2S)-N,N′-bis-(Boc)-3-(2- pyrrolyl)alanines (10, 3, and 14, respectively) were made in 13-17% overall yields and six to seven steps from oxazolidine β-methyl ester 4. Homoallylic ketone 5 was prepared by a copper-catalyzed cascade addition of vinylmagnesium bromide to ester 4 and converted to pyrrolyl amino alcohol 7 by olefin oxidation and Paal-Knorr condensation. Protecting group shuffle and oxidation of the primary alcohol enabled the synthesis of pyrrolylalanines. The bis-Boc analog 14 proved useful in peptide chemistry and was employed to make N-acetyl-pyrrolylalaninyl-proline N′′-methylamide 25. A study of the influence of the pyrrole moiety on the prolyl amide isomer equilibrium of 25 using 1H NMR spectroscopy in chloroform, DMSO, and water demonstrated that the pyrrolylalanine peptide exhibited behavior and conformations different from those of other arylalanine analogs.

Synthesis and peptide coupling of protected 2-pyrrolylalanine

D?rr, Aurélie A.,Lubell, William D.

, p. 2159 - 2161 (2011/05/05)

2-Pyrrolylalanine has been synthesized in two protected forms and applied in the solution-phase synthesis of a dipeptide. (2S)-N-(Boc)-N′- (phenylsulfonyl)- and (2S)-N,N′-bis-(phenylsulfonyl)-3-(2-pyrrolyl) alanines (7 and 9) were obtained, respectively, in 14% and 13% overall yields and six and seven steps from oxazolidine β-methyl ester 1, which was derived from l-aspartic acid. Homoallylic ketone 2 was obtained from a copper-catalyzed cascade addition of vinylmagnesium bromide to 1 and converted into pyrrolylalanines 7 and 9 by a sequence featuring subsequent olefin oxidation and Paal-Knorr condensation. Protected pyrrolylalanine 9 was then introduced into a dipeptide. Crown Copyright

Process route upstream and downstream products

Process route

C<sub>18</sub>H<sub>24</sub>N<sub>2</sub>O<sub>5</sub>S
1262660-95-6

C18H24N2O5S

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine
1294518-17-4

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine

Conditions
Conditions Yield
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In acetonitrile; at 35 ℃; sodium-phosphate buffer;
50%
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In acetonitrile; Inert atmosphere; aq. phosphate buffer;
C<sub>15</sub>H<sub>25</sub>NO<sub>5</sub>
1262660-92-3

C15H25NO5

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine
1294518-17-4

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: ammonium formate; sodium acetate; acetic acid / acetonitrile / 65 °C
2: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / 0 °C
3: water; acetic acid / 50 °C
4: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 35 °C / sodium-phosphate buffer
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 18-crown-6 ether; potassium tert-butylate; water; ammonium formate; sodium acetate; acetic acid; In tetrahydrofuran; acetonitrile; 1: Paal-Knorr condensation;
Multi-step reaction with 4 steps
1: ammonium formate; sodium acetate; acetic acid / acetonitrile / 65 °C / Inert atmosphere
2: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / 0 °C / Inert atmosphere
3: acetic acid / water / 50 °C / Inert atmosphere
4: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / Inert atmosphere; aq. phosphate buffer
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 18-crown-6 ether; potassium tert-butylate; ammonium formate; sodium acetate; acetic acid; In tetrahydrofuran; water; acetonitrile; 1: Paal-Knorr condensation;
C<sub>15</sub>H<sub>24</sub>N<sub>2</sub>O<sub>3</sub>
1262660-93-4

C15H24N2O3

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine
1294518-17-4

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / 0 °C
2: water; acetic acid / 50 °C
3: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 35 °C / sodium-phosphate buffer
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 18-crown-6 ether; potassium tert-butylate; water; acetic acid; In tetrahydrofuran; acetonitrile;
Multi-step reaction with 3 steps
1: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / 0 °C / Inert atmosphere
2: acetic acid / water / 50 °C / Inert atmosphere
3: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / Inert atmosphere; aq. phosphate buffer
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 18-crown-6 ether; potassium tert-butylate; acetic acid; In tetrahydrofuran; water; acetonitrile;
C<sub>21</sub>H<sub>28</sub>N<sub>2</sub>O<sub>5</sub>S
1262660-94-5

C21H28N2O5S

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine
1294518-17-4

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: water; acetic acid / 50 °C
2: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 35 °C / sodium-phosphate buffer
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; water; acetic acid; In acetonitrile;
Multi-step reaction with 2 steps
1: acetic acid / water / 50 °C / Inert atmosphere
2: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / Inert atmosphere; aq. phosphate buffer
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; acetic acid; In water; acetonitrile;
C<sub>16</sub>H<sub>27</sub>NO<sub>4</sub>
940312-40-3

C16H27NO4

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine
1294518-17-4

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water
2: ammonium formate; sodium acetate; acetic acid / acetonitrile / 65 °C
3: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / 0 °C
4: water; acetic acid / 50 °C
5: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 35 °C / sodium-phosphate buffer
With 2,6-dimethylpyridine; sodium hypochlorite; sodium chlorite; sodium periodate; osmium(VIII) oxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 18-crown-6 ether; potassium tert-butylate; water; ammonium formate; sodium acetate; acetic acid; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile; 2: Paal-Knorr condensation;
Multi-step reaction with 5 steps
1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / Inert atmosphere
2: ammonium formate; sodium acetate; acetic acid / acetonitrile / 65 °C / Inert atmosphere
3: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / 0 °C / Inert atmosphere
4: acetic acid / water / 50 °C / Inert atmosphere
5: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / Inert atmosphere; aq. phosphate buffer
With 2,6-dimethylpyridine; sodium hypochlorite; sodium chlorite; sodium periodate; osmium(VIII) oxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 18-crown-6 ether; potassium tert-butylate; ammonium formate; sodium acetate; acetic acid; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile; 2: Paal-Knorr condensation;
methyl [(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]ethanoate
205491-14-1

methyl [(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]ethanoate

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine
1294518-17-4

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: copper(l) cyanide / tetrahydrofuran / -45 °C
2: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water
3: ammonium formate; sodium acetate; acetic acid / acetonitrile / 65 °C
4: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / 0 °C
5: water; acetic acid / 50 °C
6: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 35 °C / sodium-phosphate buffer
With 2,6-dimethylpyridine; sodium hypochlorite; sodium chlorite; sodium periodate; osmium(VIII) oxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 18-crown-6 ether; potassium tert-butylate; water; ammonium formate; sodium acetate; copper(l) cyanide; acetic acid; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile; 3: Paal-Knorr condensation;
Multi-step reaction with 6 steps
1: copper(l) cyanide / tetrahydrofuran / -45 °C / Inert atmosphere
2: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / Inert atmosphere
3: ammonium formate; sodium acetate; acetic acid / acetonitrile / 65 °C / Inert atmosphere
4: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / 0 °C / Inert atmosphere
5: acetic acid / water / 50 °C / Inert atmosphere
6: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / Inert atmosphere; aq. phosphate buffer
With 2,6-dimethylpyridine; sodium hypochlorite; sodium chlorite; sodium periodate; osmium(VIII) oxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 18-crown-6 ether; potassium tert-butylate; ammonium formate; sodium acetate; copper(l) cyanide; acetic acid; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile; 3: Paal-Knorr condensation;

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