N-CARBOBENZOXY-L-SERINE BETA-LACTONE

Product Name: N-CARBOBENZOXY-L-SERINE BETA-LACTONE
CAS No.: 26054-60-4
Chemical Name: N-CARBOBENZOXY-L-SERINE BETA-LACTONE
Synonyms: Z-Ser-β-Lactone;Cbz-L-Serine β-Lactone;N-Cbz-L-serine β-Lactone;carbobenzoxyserinelactone;N-CBZ-L-SERINE BETA-LACTONE;(S)-N-Cbz-3-aminooxetan-2-one;N-Carbobenzoxy-L-serine β-lactone;N-Carbobenzoxy-L-serine β-Lactone;N-CARBOBENZYLOXY-L-SERINE B-LACTONE;N-Carbobenzyloxy-L-serine β-Lactone
CBNumber: CB4117478
Molecular Formula: C11H11NO4
Formula Weight: 221.21
MOL File: 26054-60-4.mol

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N-CARBOBENZOXY-L-SERINE BETA-LACTONE Property

Melting point:: 129-130°C
Boiling point:: 425.5±44.0 °C(Predicted)
Density: 1.31±0.1 g/cm3(Predicted)
refractive index: -25.5 ° (C=1, CH3CN)
storage temp.: Inert atmosphere,2-8°C
solubility: Acetonitrile (Sparingly, Sonicated), Chloroform (Slightly), Methanol (Slightly)
pka: 10.32±0.20(Predicted)
form: powder to crystal
color: White to Almost white
optical activity: -24.401° (C=1.00 g/100ml, ACN)
InChIKey: CWFZPRQDHIUBDO-VIFPVBQESA-N

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Safety

HS Code: 2932.20.4500

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TCI Chemical

Product number: C1575
Product name: N-Carbobenzoxy-L-serine beta-Lactone
Purity: >98.0%(HPLC)
Packaging: 1g
Price: $569
Updated: 2025/07/31

TRC

Product number: C176540
Product name: N-Carbobenzyloxy-L-serineβ-Lactone
Packaging: 25g
Price: $1425
Updated: 2021/12/16

TRC

Product number: C176540
Product name: N-Carbobenzyloxy-L-serineβ-Lactone
Packaging: 2g
Price: $450
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FC04687
Product name: N-Cbz-L-serine-b-lactone
Packaging: 1g
Price: $280
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 50178
Product name: N-Carbobenzyloxy-L-serineβ-Lactone
Packaging: 100mg
Price: $625
Updated: 2021/12/16

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N-CARBOBENZOXY-L-SERINE BETA-LACTONE Chemical Properties,Usage,Production

Chemical Properties

White Foam

Uses

N-Carbobenzyloxy-L-serine β-Lactone (cas# 26054-60-4) is a compound useful in organic synthesis.

Application

N-Carbobenzyloxy-L-serine β-Lactone is a reagent for the synthesis of β-substituted alanines.

Synthesis

1145-80-8

26054-60-4

General procedure for the synthesis of benzyl (S)-(2-oxooxetan-3-yl)carbamate from N-benzyloxycarbonyl-L-serine: Step 4-1. Synthesis of Z-serine-β-lactone (AA4-2). This intermediate was prepared in a similar way to the previously described synthesis of the Boc derivative AA3-1. Triphenylphosphine (4.5 g, 17.1 mmol, 1.1 eq.) was added to a dry 250 mL three-necked flask (equipped with a mechanical stirrer) under nitrogen protection, followed by the addition of 100 mL of a solvent mixture of anhydrous THF and CH3CN (1:9, v/v). The mixture was stirred until completely dissolved, then cooled to -55 °C (bath temperature) and dimethyl azodicarboxylate (DMAD, 1.9 mL, 17.1 mmol, 1.1 eq.) was added dropwise over 10 min. After addition, stirring was continued for 20 min, and then Z-Ser-OH (AA4-1, 3.7 g, 15.5 mmol, 1.0 eq.) dissolved in 50 mL of anhydrous THF mixed with CH3CN solvent (1:9, v/v) was added dropwise over 30 min. The reaction mixture was stirred at -55 °C for 1.5 h. After removing the cooling bath, the reaction system was allowed to slowly warm up to room temperature. After the reaction mixture reached room temperature, the solvent was removed by concentration under reduced pressure. The resulting yellow oil was purified by fast chromatography [elution gradient: hexane/EtOAc (80:20) to (60:40)] to give 2.5 g of AA4-2 as a white solid in 72% yield. Purification of the crude product is recommended to be carried out on the same day to avoid decomposition. DCM can be added if necessary to help dissolve the residue.TLC conditions: hexane/EtOAc (60:40), Rf = 0.55 (UV, CMA).

storage

N-Carbobenzyloxy-L-serine β-Lactone is stable for many months at 4 °C in dry form. Neutral or slightly acidic solutions of N-Carbobenzyloxy-L-serine β-Lactone is stable for at least 1 day.

References

[1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 22, p. 2643 - 2646
[2] Patent: US2010/93720, 2010, A1. Location in patent: Page/Page column 38
[3] Journal of the American Chemical Society, 1985, vol. 107, # 24, p. 7105 - 7109
[4] Organic and Biomolecular Chemistry, 2008, vol. 6, # 18, p. 3240 - 3243
[5] Organic Syntheses, 1992, vol. 70, p. 1 - 1

N-CARBOBENZOXY-L-SERINE BETA-LACTONE Preparation Products And Raw materials

Raw materials

Preparation Products

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N-CARBOBENZOXY-L-SERINE BETA-LACTONE Suppliers

Americas 1 Canada 1 China 91 Europe 2 Germany 4 India 4 United Kingdom 4 United States 12 Global 119

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View Lastest Price from N-CARBOBENZOXY-L-SERINE BETA-LACTONE manufacturers

Career Henan Chemical Co

Product: N-CARBOBENZOXY-L-SERINE BETA-LACTONE 26054-60-4
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 150KG
Release date: 2019-07-09

26054-60-4, N-CARBOBENZOXY-L-SERINE BETA-LACTONERelated Search:

N-CARBOBENZOXY-DL-ASPARTIC ACID N-Carbobenzyloxyglycine N-Carbobenzyloxy-D-asparagine N-CARBOBENZOXY-DL-SERINE N-CARBOBENZOXY-DL-VALINE N-Cbz-L-serine methyl ester N-ALPHA-CARBOBENZOXY-L-SERINE T-BUTYL ESTER L-1-Phenylethylamine N-Cbz-L-Serine 2-Oxetanone 3-OXETANAMINE N-CARBOBENZOXY-L-SERINE BETA-LACTONE

(S)-ALPHA-CARBOBENZOXYAMINO-BETA-PROPIOLACTONE

N-CBZ-L-SERINE BETA-LACTONE

benzyl N-[(3S)-2-oxooxetan-3-yl]carbamate

N-CARBOBENZOXY-L-SERINE BETA-LACTONE

N-CARBOBENZYLOXY-L-SERINE B-LACTONE

carbobenzoxyserinelactone

Carbamic acid, [(3S)-2-oxo-3-oxetanyl]-, phenylmethyl ester (9CI)

N-CARBOBENZOXY-L-SERINE ALPHA-LACTONE

(S)-benzyl 2-oxooxetan-3-ylcarbamate

N-Carbobenzoxy-L-serine β-Lactone

(S)-N-(Benzyloxycarbonyl)-3-aMino-2-oxetanone

N-[(3S)-2-Oxo-3-oxetanyl]carbaMic Acid PhenylMethyl Ester

(S)-alpha-Carbobenzoxyamino-beta-propiolactone N-Cbz-L-serine beta-Lactone

N-(Benzyloxycarbonyl)-L-serine b-lactone

N-Carbobenzyloxy-L-serine beta-Lactone

REF DUPL: N-Carbobenzoxy-L-serine beta-lactone

(S)-N-Cbz-3-aminooxetan-2-one

Serine, N-carboxy-, β-lactone, benzyl ester, L- (8CI)

N-Carbobenzoxy-L-serine β-Lactone &gt

Carbamic acid, N-[(3S)-2-oxo-3-oxetanyl]-, phenylmethyl ester

Z-Ser-β-Lactone

N-Carbobenzyloxy-L-serine β-Lactone

(S)-alpha-Benzyloxycarbonylamino-beta-propiolactone

N-Cbz-L-serine β-Lactone

Cbz-L-Serine β-Lactone

N-Carbobenzoxy-L-serine β-lactone

26054-60-4

Simple 4-Membered Ring Compounds

Oxetanes

Amino Acids & Derivatives

Chiral Reagents

N-CBZ

Oxetanes

Simple 4-Membered Ring Compounds