(R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate

Base Information

• Chemical Name: (R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate
• CAS No.: 75443-62-8
• Molecular Formula: C12H11NO5
• Molecular Weight: 249.223
• DSSTox Substance ID: DTXSID40497273
• Wikidata: Q72505503
• Mol file: 75443-62-8.mol

Synonyms:75443-62-8;(R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate;BENZYL N-[(3R)-2,5-DIOXOOXOLAN-3-YL]CARBAMATE;(R)-3-(Cbz-amino)dihydrofuran-2,5-dione;D-Benzyloxycarbonylaspartic Anhydride;Carbamic acid, N-[(3R)-tetrahydro-2,5-dioxo-3-furanyl]-, phenylmethyl ester;SCHEMBL377134;(R)-Benzyl(2,5-dioxotetrahydrofuran-3-yl)carbamate;benzyl (R)-(2,5-dioxotetrahydrofuran-3-yl)carbamate;DTXSID40497273;OZPYEGOBGWQOSZ-SECBINFHSA-N;(r)-N-cbz-aspartic acid anhydride;AC9199;N-(Benzyloxycarbonyl)-D-aspartic anhydride;Benzyl [(3R)-2,5-dioxooxolan-3-yl]carbamate;(R)-benzyl 2,5-dioxotetrahydrofuran-3-ylcarbamate;A917727;benzyl (3R)-2,5-dioxotetrahydro-3-furanylcarbamate;Q-103497

Chemical Property of (R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate

Chemical Property:

• PSA: 85.19000
• Density: 1.37
• LogP: 0.95930
• 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:

99% ^*data from raw suppliers

(R)-Benzyl(2,5-dioxotetrahydrofuran-3-yl)carbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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 (R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate

There total 4 articles about (R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)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-(benzyloxycarbonyl)-D-aspartic acid (78663-07-7) → benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamate (75443-62-8)

Guidance literature:

With acetic anhydride; at 18 - 25 ℃;

Reference yield:

N-Cbz-L-Asp (1152-61-0) → benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamate (75443-62-8) + N-benzyloxycarbonyl-L-aspartic acid anhydride (4515-23-5)

Guidance literature:

With acetic anhydride; at 20 - 45 ℃; for 2.25h; Further Variations:; Reagents; Solvents; Temperatures; Product distribution;

DOI:10.1016/j.tetasy.2007.07.003

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamate (75443-62-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water; acetone / 7 h / 0 - 20 °C

2: acetic anhydride / 2 h / 20 °C

With acetic anhydride; sodium hydroxide; In water; acetone;

DOI:10.14233/ajchem.2013.14200

upstream raw materials:

N-(benzyloxycarbonyl)-D-aspartic acid

N-Cbz-L-Asp

benzyl chloroformate

Downstream raw materials:

(R)-4-benzyloxycarbonylamino-4,5-dihydro-2(3H)-furanone

(R)-3-carbobenzyloxy-amino-1-hydroxysuccinimde

Refernces

• 1、 Lee, Do-Hun. "Synthesis and anticonvulsant evaluation of (R)-and (S)-3-carbobenzyloxy- amino-1-oxysuccinimides". . p. 5948 - 5950. Retrieved 2013/07/26.
• 2、 Eswaran, Sumesh,Adhikari, Airody Vasudeva,Pal, Nishith K.,Chowdhury, Imran H.. "Design and synthesis of some new quinoline-3-carbohydrazone derivatives as potential antimycobacterial agents". supporting information; experimental part. p. 1040 - 1044. Retrieved 2010/06/14.