N-(Benzyloxycarbonyloxy)succinimide

Base Information

• Chemical Name: N-(Benzyloxycarbonyloxy)succinimide
• CAS No.: 13139-17-8
• Molecular Formula: C12H11NO5
• Molecular Weight: 249.223
• Hs Code.: 29252900
• European Community (EC) Number: 236-075-3
• DSSTox Substance ID: DTXSID20157020
• Nikkaji Number: J208.262D
• Wikidata: Q72442079
• Mol file: 13139-17-8.mol

Synonyms:N-(Benzyloxycarbonyloxy)succinimide;13139-17-8;benzyl (2,5-dioxopyrrolidin-1-yl) carbonate;cbz-osu;Z-OSu;Benzyl succinimido carbonate;cbz-onsu;MFCD00005513;Benzyl N-succinimidyl carbonate;benzyl 2,5-dioxopyrrolidin-1-yl carbonate;2,5-Pyrrolidinedione, 1-[[(phenylmethoxy)carbonyl]oxy]-;n-(benzyloxycarbonyloxy) succinimide;N-(Benzyloxycarbonyloxy)-succinimide;N-Carbobenzoxyoxysuccinimide;EINECS 236-075-3;1-{[(benzyloxy)carbonyl]oxy}pyrrolidine-2,5-dione;cbzosu;2,5-Pyrrolidinedione, 1-(((phenylmethoxy)carbonyl)oxy)-;N-(Benzyloxy carbonyloxy)succinimide;Z-ONSU;2,5-dioxoazolidinyl (phenylmethoxy)formate;CBZ-O-NHS;O-Cbz-N-hydroxysuccinimide;benzyl succinimidyl carbonate;Oprea1_125035;SCHEMBL142445;n-benzyloxycarbonyloxy succinimide;n-benzyloxycarbonyloxy-succinimide;DTXSID20157020;N-(benzyloxy)carbonyloxy succinimid;CS-D0812;N-(benzyl-oxycarbonyloxy)succinimide;N-(benzyloxy-carbonyloxy)-succinimid;N-(benzyloxycarbonyl-oxy)succinimide;N-(Benzyloxy-carbonyloxy)-succinimide;N-(benzyloxycarbonyloxy) -succinimide;AKOS001606658;AB00436;N|A-(Benzyloxycarbonyloxy) Succinimide;RS-0117;AC-11912;Benzyl 2,5-dioxopyrrolidin-1-ylcarbonate;BP-12325;BP-23497;N-(Benzyloxycarbonyloxy)succinimide, 98%;SY001454;AM20020391;FT-0629266;EN300-175786;SR-01000408144;1-{[(benzyloxy)carbonyl]oxy}-2,5-pyrrolidinedione;Q-101762;SR-01000408144-1;1-[[(phenylmethoxy)carbonyl]oxy]-2,5-pyrrolidinedione;1-({[(Phenylmethyl)oxy]carbonyl}oxy)-2,5-pyrrolidinedione;carbonic acid benzyl ester 2,5-dioxo-pyrrolidin-1-yl ester;Carbonic acid benzyl ester 2,5-dioxopyrrolidin-1-yl ester;Z-OSu?Cbz-OSu;N| cent-(Benzyloxycarbonyloxy) Succinimide

Chemical Property of N-(Benzyloxycarbonyloxy)succinimide

Chemical Property:

• Appearance/Colour: white crystal powde
• Vapor Pressure: 1.23E-05mmHg at 25°C
• Melting Point: 80-82 °C(lit.)
• Refractive Index: 1.583
• Boiling Point: 369 °C at 760 mmHg
• Flash Point: 177 °C
• PSA: 72.91000
• Density: 1.38 g/cm³
• LogP: 1.34170
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: acetone: 0.1 g/mL, clear
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 249.06372245
• Heavy Atom Count: 18
• Complexity: 332

Purity/Quality:

99% ^*data from raw suppliers

Z-Onsu ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 43-24/25-36/37/38-20/21/22
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)OCC2=CC=CC=C2
• Uses: Reagents for the selective introduction of the Z-protecting group into amino compounds 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. 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.

Technology Process of N-(Benzyloxycarbonyloxy)succinimide

There total 6 articles about N-(Benzyloxycarbonyloxy)succinimide 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: 90.5%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + benzyl chloroformate (501-53-1,94274-21-2) → N-(Benzyloxycarbonyloxy)succinimide (13139-17-8)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate; at 15 ℃; for 19h; Large scale;

Reference yield: 90.0%

dicyclohexylamine salt of N-hydroxysuccinimide (82911-72-6) + benzyl chloroformate (501-53-1,94274-21-2) → N-(Benzyloxycarbonyloxy)succinimide (13139-17-8)

Guidance literature:

In chloroform;

DOI:10.1139/v82-146

Reference yield: 52.7%

succinic acid anhydride (108-30-5) + benzyl chloroformate (501-53-1,94274-21-2) → N-(Benzyloxycarbonyloxy)succinimide (13139-17-8)

Guidance literature:

succinic acid anhydride; With hydroxylamine sulfate; In water; Alkaline conditions;

With phosphoric acid; In water; toluene; Reflux; Alkaline conditions;

benzyl chloroformate; In toluene; for 2h; Reagent/catalyst;

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

benzyl chloroformate

dicyclohexylamine salt of N-hydroxysuccinimide

di(succinimido) carbonate

Downstream raw materials:

(2S,3S)-2-(benzyloxycarbonylamino)-3-methylsuccinic acid

(2S,3R)-N-benzyloxycarbonyl-3-methylaspartic acid dimethyl ester

N-(Benzyloxycarbonyl)glycine

N-[(benzyloxy)carbonyl]-L-histidine

Refernces

• 1、 Kawaguchi,Naito,Nakagawa,Fujisawa. "BB-K 8, a new semisynthetic aminoglycoside antibiotic.". . p. 695 - 708. Retrieved 1972.
• 2、 -. "Synthesis method of N-(benzyloxycarbonyloxy)succinimide". Paragraph 0005; 0008; 0010-0012; 0013; 0014; 0016; 0017. . Retrieved 2020/05/05.
• 3、 -. "AMIDO ANTI-VIRAL COMPOUNDS". Page/Page column 72; 83-85; 86-87; 98-99; 125. . Retrieved 2008/12/05.