Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate

Base Information

• Chemical Name: Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate
• CAS No.: 118399-28-3
• Molecular Formula: C12H13NO4
• Molecular Weight: 235.24
• Hs Code.: 29321900
• European Community (EC) Number: 821-246-2,944-412-7
• DSSTox Substance ID: DTXSID90351331
• Nikkaji Number: J2.885.913I
• Wikidata: Q72441716
• Mol file: 118399-28-3.mol

Synonyms:118399-28-3;Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate;benzyl N-[(3R)-5-oxooxolan-3-yl]carbamate;(R)-Benzyl 5-oxotetrahydrofuran-3-ylcarbamate;(R)-3-(Cbz-amino)-5-oxotetrahydrofuran;(R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate;(R)-Benzyl-5-oxo-tetrahydro-furan-3-ylcarbamate;3(R)-[(Carbobenzyloxy)amino]-gamma-butyrolactone;Carbamic acid, [(3R)-tetrahydro-5-oxo-3-furanyl]-, phenylmethyl ester;MFCD09839299;Benzyl (R)-Tetrahydro-5-oxo-3-furanylcarbamate;(R)-beta-(Carbobenzoxyamino)-gamma-butyrolactone;Oprea1_012853;SCHEMBL382338;DTXSID90351331;BNIBNUOPVTZWRT-SNVBAGLBSA-N;CS-D0923;AKOS005146348;AKOS015855249;AC-5674;(R)-4-(Cbz-amino)tetrahydrofuran-2-one;AS-18891;(R)-beta-(Cbz-amino)-gamma-butyrolactone;Benzyl [(3R)-5-oxooxolan-3-yl]carbamate;AM20050326;C2678;benzyl(3R)-5-oxotetrahydro-3-furanylcarbamate;(R)-benzyl-5-oxotetrahydrofuran-3-yl carbamate;(S)-benzyl 5-oxo-tetrahydrofuran-3-ylcarbamate;3(R)-[(Carbobenzyloxy)amino]-?-butyrolactone;benzyl (3r)-5-oxotetrahydro-3-furanylcarbamate;(R)-4-(Carbobenzoxyamino)tetrahydrofuran-2-one;(R)-Benzyl(5-oxotetrahydrofuran-3-yl)carbamate;benzyl (r)-(5-oxotetrahydrofuran-3-yl)carbamate;A803921;benzyl(r)-(5-oxo-tetrahydrofuran-3-yl)-carbamate;benzyl (r)-(5-oxo-tetrahydrofuran-3-yl)-carbamate;J-502250;N-benzyl-N-(5-oxotetrahydrofuran-3-yl)carbamate

Chemical Property of Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 7.29E-09mmHg at 25°C
• Melting Point: 105.0 to 109.0 °C
• Refractive Index: 1.56
• Boiling Point: 466.087 °C at 760 mmHg
• PKA: 10.87±0.20(Predicted)
• Flash Point: 235.681 °C
• PSA: 64.63000
• Density: 1.272 g/cm³
• LogP: 1.61920
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 235.08445790
• Heavy Atom Count: 17
• Complexity: 286

Purity/Quality:

99.5% ^*data from raw suppliers

3(R)-[(Carbobenzyloxy)amino]-γ-butyrolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(COC1=O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1[C@H](COC1=O)NC(=O)OCC2=CC=CC=C2
• Uses: 3(R)-[(Carbobenzyloxy)amino]-γ-butyrolactone (cas# 118399-28-3) is a compound useful in organic synthesis.

Technology Process of Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate

There total 13 articles about Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate 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: 99.0%

C14H13F3N2O5 (1256257-81-4) → (R)-4-benzyloxycarbonylamino-4,5-dihydro-2(3H)-furanone (118399-28-3)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201000695

Reference yield: 85.0%

benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamate (75443-62-8) → (R)-4-benzyloxycarbonylamino-4,5-dihydro-2(3H)-furanone (118399-28-3)

Guidance literature:

benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamate; With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 20 ℃; for 4h;

With hydrogenchloride; In tetrahydrofuran; water; pH=2;

Reference yield: 83.0%

(R)-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid (123673-31-4) → (R)-4-benzyloxycarbonylamino-4,5-dihydro-2(3H)-furanone (118399-28-3)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 3h; Dean-Stark conditions; Reflux;

upstream raw materials:

benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamate

(R)-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid

(S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

(2R)-aspartic acid

Downstream raw materials:

C₂₄H₂₆F₃N₃O₅

benzyl [(3R,4R)-4-allyl-5-oxotetrahydrofuran-3-yl]carbamate

Methylester of (R)-4-hydroxy-3-(benzyloxycarbonylamino) Butanoic Acid

(R)-methyl 3-(benzyloxycarbonylamino)-4-(phenylthio)butanoate

Refernces

• 1、 Rodríguez-Mata, María,Lavandera, Iván,Gotor-Fernández, Vicente,Gotor, Vicente,García-Cerrada, Susana,Mendiola, Javier,de Frutos, óscar,Collado, Iván. "Baeyer–Villiger monooxygenase-catalyzed desymmetrizations of cyclobutanones. Application to the synthesis of valuable spirolactones". supporting information. p. 7268 - 7275. Retrieved 2016/10/26.
• 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.