(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

Base Information

• Chemical Name: (S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate
• CAS No.: 4515-23-5
• Molecular Formula: C12H11NO5
• Molecular Weight: 249.223
• Hs Code.: 2924299090
• European Community (EC) Number: 224-838-3
• UNII: T519K4TV9T
• DSSTox Substance ID: DTXSID70196404
• Nikkaji Number: J92.445H
• Wikidata: Q27289678
• Mol file: 4515-23-5.mol

Synonyms:4515-23-5;N-Carbobenzyloxy-L-aspartic anhydride;N-Cbz-L-Aspartic anhydride;Cbz-L-Aspartic anhydride;(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate;benzyl N-[(3S)-2,5-dioxooxolan-3-yl]carbamate;N-(Benzyloxycarbonyl)-L-aspartic acid anhydride;UNII-T519K4TV9T;T519K4TV9T;EINECS 224-838-3;benzyl (S)-(2,5-dioxotetrahydrofuran-3-yl)carbamate;N-benzyloxycarbonyl-L-aspartic anhydride;N-Z-L-aspartic anhydride;Carbamic acid, (tetrahydro-2,5-dioxo-3-furanyl)-, phenylmethyl ester, (S)-;N-carbobenzoxy-l-aspartic anhydride;D-Benzyloxycarbonylaspartic Anhydride;(S)-2-BENZYLOXYCARBAMYLSUCCINIC ANHYDRIDE;(2,5-Dioxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester;SCHEMBL732094;(S)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate;N-carbobenzoxy-aspartic anhydride;DTXSID70196404;N-Z-L-aspartic anhydride, 95%;OZPYEGOBGWQOSZ-VIFPVBQESA-N;(S)-(2,5-Dioxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester;CBZ-L-ASPARTIC ACID ANHYDRIDE;MFCD00136820;AKOS015888879;N-Benzyloxycarbonyl Aspartic Anhydride;CS-W010219;HY-W009503;AS-37185;AM20040502;N-benzyloxycarbonyl-L-aspartic acid anhydride;N-CARBOBENZOXY-L-ASPARTIC ACID ANHYDRIDE;(S)-benzyl 2,5-dioxotetrahydrofuran-3-ylcarbamate;A847745;Aspartic anhydride, N-carboxy-, benzyl ester, L-;N-(BENZYLOXYCARBONYL)-L-ASPARTIC ANHYDRIDE;Q-103507;.BETA.-BENZYL L-ASPARTATE N-CARBOXYL ANHYDRIDE;N-(BENZYLOXYCARBONYL)ASPARTIC ANHYDRIDE, (S)-;Q27289678;ASPARTIC ANHYDRIDE, N-CARBOXY-, N-BENZYL ESTER, L-;CARBAMIC ACID, ((3S)-TETRAHYDRO-2,5-DIOXO-3-FURANYL)-, PHENYLMETHYL ESTER

Chemical Property of (S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

Chemical Property:

• Appearance/Colour: White Powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 123-124 °C(lit.)
• Refractive Index: 1.573
• Boiling Point: 490.2 °C at 760 mmHg
• PKA: 9.93±0.20(Predicted)
• Flash Point: 250.3 °C
• PSA: 81.70000
• Density: 1.37 g/cm³
• LogP: 1.14580
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 249.06372245
• Heavy Atom Count: 18
• Complexity: 348

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Cbz-L-asparticanhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(=O)OC1=O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1[C@@H](C(=O)OC1=O)NC(=O)OCC2=CC=CC=C2

Technology Process of (S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

There total 5 articles about (S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate 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: 100.0%

N-Cbz-L-Asp (1152-61-0) → N-benzyloxycarbonyl-L-aspartic acid anhydride (4515-23-5)

Guidance literature:

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonyl-L-aspartic acid anhydride (4515-23-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent

2: 98 percent / dicyclohexylcarbodiimide / ethyl acetate / 1.) 1 h, 0 deg C, 2.) 24 h, r.t.

With dicyclohexyl-carbodiimide; In ethyl acetate;

DOI:10.1246/bcsj.62.2748

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → N-benzyloxycarbonyl-L-aspartic acid anhydride (4515-23-5)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene / anfangs unter Kuehlung

2: MgO; water; diethyl ether

3: acetic acid anhydride

With diethyl ether; water; acetic anhydride; magnesium oxide; toluene;

upstream raw materials:

N-Cbz-L-Asp

benzyl chloroformate

benzyl alcohol

Downstream raw materials:

N-(N-benzyloxycarbonyl-L-α-aspartyl)-L-valine methyl ester

N-(N-benzyloxycarbonyl-L-β-aspartyl)-L-valine methyl ester

N-(N-benzyloxycarbonyl-L-α-aspartyl)-L-glutamic acid diethyl ester

N-(N-benzyloxycarbonyl-L-α-aspartyl)-glycine ethyl ester

Refernces

• 1、 -. "A PREPARATION METHOD OF SITAGLIPTIN". Page/Page column 12; 13. . Retrieved 2012/11/13.
• 2、 Crich, David,Bowers, Albert A.. "Cyclic thioanhydrides: Linchpins for multicomponent coupling reactions based on the reaction of thioacids with electron-deficient sulfonamides and azides". . p. 5323 - 5325. Retrieved 2008/09/17.