N-(TERT-BUTOXYCARBONYL)-L-SERINE BETA-LACTONE
- Product Name
- N-(TERT-BUTOXYCARBONYL)-L-SERINE BETA-LACTONE
- CAS No.
- 98541-64-1
- Chemical Name
- N-(TERT-BUTOXYCARBONYL)-L-SERINE BETA-LACTONE
- Synonyms
- N-Boc-
L<;-serine beta-L;Boc L-Serine β-Lactone;N-Boc L-Serine -Lactone;N-Boc L-Serine b-Lactone;N-Boc L-Serine β-Lactone;Boc-L-Serine-beta-Lactone;N-BOC-L-SERINE BETA-LACTONE;(S)-3-BOC-AMINO-2-OXOOXETANE;N-Boc-L-serine β-lactone, >=97% - CBNumber
- CB1741953
- Molecular Formula
- C8H13NO4
- Formula Weight
- 187.19
- MOL File
- 98541-64-1.mol
N-(TERT-BUTOXYCARBONYL)-L-SERINE BETA-LACTONE Property
- Melting point:
- 117-119 °C
- Boiling point:
- 319.0±31.0 °C(Predicted)
- Density
- 1.18±0.1 g/cm3(Predicted)
- refractive index
- -26 ° (C=1, CH3CN)
- storage temp.
- Inert atmosphere,Store in freezer, under -20°C
- solubility
- Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol(Slightly)
- pka
- 10.53±0.20(Predicted)
- form
- Solid
- color
- White to Off-White
- Stability:
- Unstable in Solution
- InChI
- InChI=1S/C8H13NO4/c1-8(2,3)13-7(11)9-5-4-12-6(5)10/h5H,4H2,1-3H3,(H,9,11)/t5-/m0/s1
- InChIKey
- HRJDEHQWXAPGBG-YFKPBYRVSA-N
- SMILES
- C(OC(C)(C)C)(=O)N[C@H]1COC1=O
- CAS DataBase Reference
- 98541-64-1
Safety
- Safety Statements
- 24/25
- HS Code
- 29322090
N-Bromosuccinimide Price
- Product number
- B1995
- Product name
- N-(tert-Butoxycarbonyl)-L-serine beta-Lactone
- Purity
- >98.0%(N)
- Packaging
- 1g
- Price
- $443
- Updated
- 2025/07/31
- Product number
- B1995
- Product name
- N-(tert-Butoxycarbonyl)-L-serine beta-Lactone
- Purity
- >98.0%(N)
- Packaging
- 5g
- Price
- $1330
- Updated
- 2025/07/31
- Product number
- B2526-85
- Product name
- N-Boc L-Serine b-Lactone
- Packaging
- 500mg
- Price
- $425
- Updated
- 2021/12/16
- Product number
- B667390
- Product name
- N-BocL-Serineβ-Lactone
- Packaging
- 2.5g
- Price
- $945
- Updated
- 2021/12/16
- Product number
- FB31428
- Product name
- Boc-L-serine-b-lactone
- Packaging
- 250mg
- Price
- $50
- Updated
- 2021/12/16
N-(TERT-BUTOXYCARBONYL)-L-SERINE BETA-LACTONE Chemical Properties,Usage,Production
Chemical Properties
White powder
Uses
An important -lactone inhibitor
Synthesis
3262-72-4
98541-64-1
The general procedure for the synthesis of N-(tert-butoxycarbonyl)-L-serine-β-lactone (AA2-1) from Boc-L-serine was as follows: to a dry 250 mL three-necked flask (equipped with a mechanical stirrer) under nitrogen protection was added triphenylphosphine (4.5 g, 17.1 mmol, 1.1 equiv.) and 100 mL of anhydrous THF:CH3CN (1:9 ) solvent mixture. The mixture was stirred until completely dissolved and then cooled to -55 °C (bath temperature). Dimethyl azodicarboxylate (DMAD, 1.9 mL, 17.1 mmol, 1.1 eq.) was slowly added dropwise over 10 minutes. After dropwise addition, stirring was continued for 20 minutes. Subsequently, Boc-Ser-OH (3.18 g, 15.5 mmol, 1.0 eq.) dissolved in 50 mL of anhydrous THF:CH3CN (1:9) was added dropwise over 30 minutes. The reaction mixture was stirred at -55 °C for 1.5 h. After removing the cooling bath, the reaction solution was allowed to slowly warm up to room temperature. After reaching room temperature, the solvent was removed by concentration under reduced pressure. The resulting yellow oil was purified by fast column chromatography [elution gradient: hexane:EtOAc (80:20) to (60:40)] to give 2.10 g AA2-1 as a white solid in 72% yield. It is recommended that purification of the feedstock be completed on the day of the reaction to avoid decomposition. DCM can be added if necessary to help dissolve the crude product.TLC assay conditions (Hex/EtOAc, 60/40): rf = 0.55 (CMA).
References
[1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 3, p. 1330 - 1340
[2] Journal of the American Chemical Society, 1985, vol. 107, # 24, p. 7105 - 7109
[3] Patent: US2010/93720, 2010, A1. Location in patent: Page/Page column 37
[4] Heterocycles, 2001, vol. 55, # 1, p. 1 - 4
[5] Journal of Medicinal Chemistry, 1996, vol. 39, # 22, p. 4430 - 4438
N-(TERT-BUTOXYCARBONYL)-L-SERINE BETA-LACTONE Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from N-(TERT-BUTOXYCARBONYL)-L-SERINE BETA-LACTONE manufacturers
- Product
- N-(TERT-BUTOXYCARBONYL)-L-SERINE BETA-LACTONE 98541-64-1
- Price
- US $1.00/g
- Min. Order
- 1g
- Purity
- 99.0%
- Supply Ability
- 100 kg
- Release date
- 2020-01-10