Introduction：Basic information about N-(Benzyloxycarbonyloxy)succinimide CAS 13139-17-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
N-(Benzyloxycarbonyloxy)succinimide Basic information
| Product Name: | N-(Benzyloxycarbonyloxy)succinimide |
| Synonyms: | BENZYLOXYCARBONYL-N-HYDROXYSUCCINIMIDE;BENZYLOXYLCARBONYLOXYSUCCINIMIDE;BENZYLOXYCARBONYLSUCCINIMIDE;BENZYLOXYCARBONYLOXYSUCCINIMIDE;BENZYL N-SUCCINIMIDYL CARBONATE;benzyl succinimido carbonate;CBZ-ONSU;CBZ-OSU |
| CAS: | 13139-17-8 |
| MF: | C12H11NO5 |
| MW: | 249.22 |
| EINECS: | 236-075-3 |
| Product Categories: | Medical Intermediates;Peptide coupling agents;Amino Acid Derivatives;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;N-Protecting Reagents;Biochemistry;Condensation & Active Esterification;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Succinimides;Peptide Synthesis;Protective Reagents (Peptide Synthesis);Synthetic Organic Chemistry;Cbz-Amino acid series |
| Mol File: | 13139-17-8.mol |
|
N-(Benzyloxycarbonyloxy)succinimide Chemical Properties
| Melting point | 80-82 °C(lit.) |
| Boiling point | 392.32°C (rough estimate) |
| density | 1.3189 (rough estimate) |
| refractive index | 1.5560 (estimate) |
| Fp | 81°C |
| storage temp. | Keep in dark place,Inert atmosphere,2-8°C |
| solubility | acetone: 0.1 g/mL, clear |
| form | Fine Crystalline Powder |
| color | White to off-white |
| Decomposition | 81 ºC |
| Sensitive | Moisture Sensitive |
| BRN | 1387927 |
| Stability: | Stable. Moisture sensitive. |
| Major Application | peptide synthesis |
| InChI | InChI=1S/C12H11NO5/c14-10-6-7-11(15)13(10)18-12(16)17-8-9-4-2-1-3-5-9/h1-5H,6-8H2 |
| InChIKey | MJSHDCCLFGOEIK-UHFFFAOYSA-N |
| SMILES | C(OCC1=CC=CC=C1)(=O)ON1C(=O)CCC1=O |
| CAS DataBase Reference | 13139-17-8(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi,Xn |
| Risk Statements | 43-24/25-36/37/38-20/21/22 |
| Safety Statements | 22-24/25-36-26 |
| WGK Germany | 3 |
| F | 8-10 |
| HS Code | 29252900 |
| Storage Class | 11 - Combustible Solids |
N-(Benzyloxycarbonyloxy)succinimide Usage And Synthesis
| Chemical Properties | white crystal powde |
| Uses | Reagents for the selective introduction of the Z-protecting group into amino compounds |
| Uses | N-(N-Benzyloxycarbonyloxy)succinimide is a reagent used in the preparation of peptide thioacids view peptide precursors. Also used in the preparation of amino glycoside derivatives for the function of topoisomerase for both human and bacterial inhibition. |
| Application | N-(Benzyloxycarbonyloxy)succinimide (Cbz-OSu) is a common reagent for the carboxybenzyl protection of amines. This reaction is one of the key synthetic steps in the synthesis of:
- Enantiomers of cyclic methionine analogs viz, (R)-and (S)-3-aminotetrahydrothiophene- 3-carboxylic acid.
- 1′-H-Spiro-(indoline-3,4′-piperidine) and its derivatives.
- Total synthesis of (-)-diazonamide A. and (-)-sanglifehrin A.
Cbz-OSu is widely employed to protect amino acid residues in peptide synthesis. It can also be used in N-trans diprotection of cyclen regioselectively. |
| Synthesis | A method for synthesizing N- (benzyloxycarbonyl) succinimide comprises the following steps of adding purified water and hydroxylamine sulfate into a reaction container, dropwise adding liquid alkali under stirring, after dropwise adding, adding succinic anhydride in batches, dehydrating at high temperature and in vacuum under acid catalysis until no water is extracted, preparing N-hydroxysuccinimide solution, adding alkali into the N-hydroxysuccinimide solution, adjusting the pH of the reaction solution, controlling the temperature to be 0 ~ 60 ℃, dropwise adding benzyl chloroformate, separating out an organic layer after dropwise adding, concentrating to be dry, and recrystallizing to obtain an N- (benzyloxycarbonyl) succinimide finished product.[1]
|
| References | [1] Method for synthesizing N- (benzyloxycarbonyl) succinimide by one-pot two-phase method. Patent No. CN110698381A |
N-(Benzyloxycarbonyloxy)succinimide Preparation Products And Raw materials
| Preparation Products | 1-Cbz-4-Piperidone-->BENZYL 3-PYRROLINE-1-CARBOXYLATE-->Cbz-D-Phenylalaninol-->N-Cbz-L-Leucine-->N-Cbz-D-Alanine-->DIBENZYL 2,2'-IMINOBIS(ETHYLCARBAMATE)-->BENZYL N-(3-HYDROXYPROPYL)CARBAMATE-->(S)-benzyl 3-(hydroxymethyl)piperazine-1-carboxylate-->(R)-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER-->N-CARBOBENZOXY-1,3-DIAMINOPROPANE HYDROCHLORIDE-->Ethyl N- Cbz -piperidine-4-carboxylate-->BENZYL 2-BROMOETHYLCARBAMATE-->N,N'-Bis(benzyloxycarbonyl)-L-cystine-->Benzyl 4-hydroxy-1-piperidinecarboxylate-->Cbz-L-tert-Leucine-->tert-Butyl 2-(1-(((Benzyloxy)carbonyl)amino)-2-methylpropan-2-yl)hydrazinecarboxylate |
