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Product Details
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Chemical Properties |
White to off-white crystalline powder |
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Uses |
Boc-3,4-Dehydro-L-Proline is an N-terminal protected 3,4-Dehydro-L-proline. It is used in solid-phase peptide synthesis (SPPS) to make peptides. 3,4-Dehydro-L-proline is a alternate substrate of the amino acid oxidase, NikD. |
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Biochem/physiol Actions |
Boc-3,4-dehydro-L-proline is a chemical compound that is commonly used in the field of organic chemistry. It is often used as a building block in the synthesis of complex molecules, such as peptides and natural products. Specifically, Boc-3,4-dehydro-L-proline is used as a proline surrogate in peptide synthesis, due to its ability to form similar secondary structures as proline. Additionally, it has been found to exhibit antimicrobial and antitumor properties, making it a potential candidate for drug development. |
IUPAC Name: (2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-2,5-dihydropyrrole-2-carboxylic acid
Isomeric SMILES: CC(C)(C)OC(=O)N1CC=C[C@H]1C(=O)O
InChIKey: BMIGSRMSSCUMAZ-ZETCQYMHSA-N
InChI: InChI=1S/C10H15NO4/c1-10(2,3)15-9(14)11-6-4-5-7(11)8(12)13/h4-5,7H,6H2,1-3H3,(H,12,13)/t7-/m0/s1
Based on the observation that an increas...
Disclosed is a method for efficiently pr...
Starting from 2-pyrrolecarboxylic acid t...
L-4-hydroxyproline methyl ester hydrochloride
(S)-2,5-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester
| Conditions | Yield |
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Multi-step reaction with 5 steps
1: dmap; triethylamine / dichloromethane / 19 h / 0 - 20 °C
2: dmap; triethylamine / dichloromethane / 5 h / 0 - 20 °C
3: sodium tetrahydroborate / tert-butyl alcohol / 80 °C
4: pyridine; dihydrogen peroxide / water; dichloromethane / 3 h / 20 °C
5: lithium hydroxide / tetrahydrofuran; water / 2 h / 20 °C
With pyridine; dmap; sodium tetrahydroborate; dihydrogen peroxide; triethylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
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N-BOC-3,4-didehydro-(S)-proline methyl ester
(S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate
1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate
1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid
(S)-2,5-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester
(2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid
| Conditions | Yield |
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N-BOC-3,4-didehydro-(S)-proline methyl ester; (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate; 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate; With sodium hydroxide; water; at 40 ℃; for 2h;
With hydrogenchloride; In water; at 5 ℃; pH=5;
With hydrogenchloride; sodium hydroxide; sodium hypochlorite; more than 3 stages; Product distribution / selectivity;
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0.01 %Chromat. 0.01 %Chromat. |
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N-BOC-3,4-didehydro-(S)-proline methyl ester; (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate; 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate; With sodium hydroxide; water; at 40 ℃; for 2h;
With hydrogenchloride; In water; pH=2; Product distribution / selectivity;
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1 %Chromat. 0.2 %Chromat. |
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N-BOC-3,4-didehydro-(S)-proline methyl ester; (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate; 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate; With bromine; In dichloromethane; at 5 - 20 ℃; for 4h;
With sodium hydroxide; water; In methanol; at 40 ℃; for 2h;
With hydrogenchloride; In methanol; water; pH=2; Product distribution / selectivity;
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0.02 %Chromat. 0.01 %Chromat. |
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N-BOC-3,4-didehydro-(S)-proline methyl ester; (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate; 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate; With sodium hydroxide; water; at 40 ℃; for 2h;
With hydrogenchloride; In water; at 5 ℃; pH=5;
With hydrogenchloride; sodium hydroxide; N-Bromosuccinimide; more than 3 stages; Product distribution / selectivity;
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0.01 %Chromat. 0.01 %Chromat. |
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N-BOC-3,4-didehydro-(S)-proline methyl ester; (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate; 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate; With sodium hydroxide; water; at 40 ℃; for 2h;
With hydrogenchloride; In water; at 5 ℃; pH=5;
With hydrogenchloride; sodium hydroxide; bromine; more than 3 stages; Product distribution / selectivity;
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0.01 %Chromat. 0.01 %Chromat. |
N-BOC-3,4-didehydro-(S)-proline methyl ester
(S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate
1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate
L-4-hydroxyproline methyl ester hydrochloride
Boc-3,4-dehydro-L-proline phenacyl ester
(S)-2-((1S,2S)-1-Benzyloxycarbonyl-2-hydroxy-2-methyl-butylcarbamoyl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester
tert-butyl {(tert-butoxycarbonyl)[(1R)-2-[(2S)-2-({[(6-cyano-3-pyridinyl)methyl]amino}carbonyl)-2,5-dihydro-1H-pyrrol-1-yl]-1-(cyclohexylmethyl)-2-oxoethyl]amino}acetate
[tert-butoxycarbonyl-(1-cyclohexylmethyl-2-oxo-2-{2-[(6-thiocarbamoyl-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-ethyl)-amino]-acetic acid tert-butyl ester
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