N-Cbz-L-homoserine lactone

Base Information

• Chemical Name: N-Cbz-L-homoserine lactone
• CAS No.: 35677-89-5
• Molecular Formula: C12H13 N O4
• Molecular Weight: 235.24
• Hs Code.: 2932209090
• Mol file: 35677-89-5.mol

Synonyms:Carbamicacid, (tetrahydro-2-oxo-3-furanyl)-, phenylmethyl ester, (S)-; Carbamic acid, [(3S)-tetrahydro-2-oxo-3-furanyl]-,phenylmethyl ester (9CI); N-Benzyloxycarbonyl-(S)-homoserine lactone;N-Benzyloxycarbonyl-L-homoserine lactone; N-Carbobenzoxy-L-homoserine lactone

Chemical Property of N-Cbz-L-homoserine lactone

Chemical Property:

• Vapor Pressure: 7.29E-09mmHg at 25°C
• Melting Point: 127-132 °C
• Boiling Point: 466.1oC at 760 mmHg
• PKA: 11.00±0.20(Predicted)
• Flash Point: 235.7oC
• PSA: 64.63000
• Density: 1.27g/cm3
• LogP: 1.61920
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

99% ^*data from raw suppliers

(S)-Benzyl(2-Oxotetrahydrofuran-3-yl)carbamate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-Cbz-L-homoserine lactone

There total 26 articles about N-Cbz-L-homoserine lactone 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-(L)-homoserine (35677-88-4) → benzyl (3S)-2-oxotetrahydro-3-furanylcarbamate (35677-89-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 23 ℃; for 16h;

DOI:10.1021/jo00376a001

Reference yield: 93.0%

(2S)-2-{[(benzyloxy)carbonyl]amino}-4-(dimethylamino)butanoic acid (62234-40-6) → benzyl (3S)-2-oxotetrahydro-3-furanylcarbamate (35677-89-5)

Guidance literature:

With propane-1,3-diyl dinitrite; In water; tert-butyl alcohol; at 120 ℃; for 0.5h; under 12929 Torr;

DOI:10.1039/d0cc03242e

Reference yield: 90.0%

tert-butyl N-[(benzyloxy)carbonyl]-L-homoserinate (78266-81-6) → benzyl (3S)-2-oxotetrahydro-3-furanylcarbamate (35677-89-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1002/ardp.19953280414

upstream raw materials:

Cbz-Met-OH

(S)-4-(Formylmethyl)-5-oxooxazolidin-3-carbonsaeure-benzylester

N-benzyloxycarbonyl-(L)-homoserine

tert-butyl N-[(benzyloxy)carbonyl]-L-homoserinate

Downstream raw materials:

benzyl L-2-<(carbobenzxyloxy)amino>-4-hydroxybutyrate

benzyl (1S)-3-hydroxy-1-{[methoxy(methyl)amino]carbonyl}propylcarbamate

((S)-1-dimethylcarbamoyl-3-hydroxy-propyl)-carbamic acid benzyl ester

N-benzyloxycarbonyl-(L)-homoserine

Refernces

• 1、 Zhang, Qiang,Queneau, Yves,Soulère, Laurent. "Biological evaluation and docking studies of new carbamate, thiocarbamate, and hydrazide analogues of ACYL homoserine lactones as vibrio fischeri-quorum sensing modulators". . p. 1 - 12. Retrieved 2020/05/25.
• 2、 Xie, Xiaomin,Stahl, Shannon S.. "Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols". supporting information. p. 3767 - 3770. Retrieved 2015/04/14.