Fmoc-L-beta-glutamic acid 5-tert-butyl ester
- Product Name
- Fmoc-L-beta-glutamic acid 5-tert-butyl ester
- CAS No.
- 209252-17-5
- Chemical Name
- Fmoc-L-beta-glutamic acid 5-tert-butyl ester
- Synonyms
- Fmoc-b-Glu(OtBu)-OH;Fmoc- -HoAsp(OtBu)-OH;Fmoc-β-HoAsp(OtBu)-OH;FMOC-BETA-GLU(OTBU)-OH;Fmoc-β-HomoAsp(OtBu)-OH;Fmoc-beta-HAsp(OtBu)-OH;FMOC-ASP(OTBU)-(C*CH2)OH;Fmoc-β-homo-Asp(OtBu)-OH;Fmoc-L-beta-HAsp(tBu)-OH;FMOC-B-HOMO-ASP(OTBU)-OH
- CBNumber
- CB5702002
- Molecular Formula
- C24H27NO6
- Formula Weight
- 425.47
- MOL File
- 209252-17-5.mol
Fmoc-L-beta-glutamic acid 5-tert-butyl ester Property
- Melting point:
- 82-83 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
- Boiling point:
- 637.0±55.0 °C(Predicted)
- Density
- 1.232±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- Powder
- pka
- 4.24±0.10(Predicted)
- color
- White to off-white
- Water Solubility
- Slightly soluble in water.
- BRN
- 7952342
- CAS DataBase Reference
- 209252-17-5(CAS DataBase Reference)
Safety
- Safety Statements
- 24/25
- WGK Germany
- 3
- HazardClass
- IRRITANT
- HS Code
- 29242990
N-Bromosuccinimide Price
- Product number
- 03689
- Product name
- Fmoc-β-Glu(OtBu)-OH
- Purity
- ≥95.0% (HPLC)
- Packaging
- 1g
- Price
- $568
- Updated
- 2023/06/20
- Product number
- 277458
- Product name
- Fmoc-L-beta-glutamic acid 5-tert-butyl ester
- Packaging
- 100mg
- Price
- $363
- Updated
- 2021/12/16
- Product number
- F632015
- Product name
- N-Fmoc-L-β-glutamicAcid5-tert-ButylEster
- Packaging
- 5g
- Price
- $940
- Updated
- 2021/12/16
- Product number
- AAA0002799
- Product name
- FMOC-L-BETA-GLUTAMIC ACID 5-TERT-BUTYL ESTER
- Purity
- 95.00%
- Packaging
- 1G
- Price
- $1027.95
- Updated
- 2021/12/16
- Product number
- 12849
- Product name
- Fmoc-L-β-glutamic acid 5--butyl ester
- Purity
- ≥ 95% (HPLC)
- Packaging
- 5G
- Price
- $890
- Updated
- 2021/12/16
Fmoc-L-beta-glutamic acid 5-tert-butyl ester Chemical Properties,Usage,Production
Chemical Properties
White to off-white powder
Uses
N-Fmoc-L-beta-glutamic acid 5-tert-butyl ester, is a protected building block used for the introduction of glutamic acid into peptides. Fmoc-beta-Glu(OtBu)-OH) was hydrolyzed with trifluoroacetic acid (TFA) and isolated with the HPLC system to give Fmoc-beta-Glu(OH)-OH.
reaction suitability
reaction type: Fmoc solid-phase peptide synthesis
Synthesis
244031-63-8
209252-17-5
The general procedure for the synthesis of (R)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid from the compound (CAS:244031-63-8) was as follows: the (R)-1-(carbonyl)-3-(tert-butoxycarbonyl)propan-2-ylcarbamate [4]aspartic acid (tBu)OH (2.0 g , 4.9 mmol, 1 equiv) was dissolved in anhydrous THF (20 mL). Triethylamine (0.74 mL, 5.4 mmol, 1.1 eq.) and ethyl chloroformate (0.52 mL, 5.4 mmol, 1.1 eq.) were added sequentially at -15 °C. Stirring was continued for 15 minutes and then the solution was allowed to warm to 0°C. Meanwhile, N-methylnitrosourea (2.5 g, 24.3 mmol, 5 eq.) was stirred in ice-cold ether (20 mL) and 40% KOH (20 mL, ice-cold) was added dropwise until completely dissolved. The yellow diazomethane solution in ether was added dropwise to the amino acid solution at 0 °C, then allowed to warm to room temperature and stirred for an additional 2.5 hours. The excess diazomethane was decomposed by dropwise addition of acetic acid. The solution was washed with saturated NaHCO3, saturated NH4Cl and brine. The organic layer was dried with Na2SO4 and evaporated under reduced pressure. The resulting diazomethane was dissolved in water/dioxane (1:5, v/v, 160 mL). After addition of silver benzoate (0.12 g, 0.5 mmol, 0.1 eq.), the mixture was sonicated in an ultrasonic bath until complete conversion (30 min) was monitored by TLC (MeOH/DCM, 1:20, Rf: 0.1-0.2). After evaporation of dioxane under reduced pressure, the solution was acidified with 5% HCl and the precipitate was extracted with EtOAc (three times). The organic layer was dried with Na2SO4 and evaporated under reduced pressure, and the crude product was purified by fast chromatography (MeOH/DCM, 1:20, Rf: 0.1-0.2) to afford [4] (1.3 g, 3.1 mmol, 63% yield).1H NMR (250 MHz, DMSO-d6): δ 12.2 (s, br, 1H), 7.90 (d, 2H), and 7.69 (dd, 2H), 7.42 (t, 2H), 7.33 (m, 3H), 4.27 (m, 3H), 3.59 (m, 1H), 2.41 (m, 4H), 1.38 (s, 9H).13C NMR (75 MHz, DMSO-d6): 172.49, 170.24, 144.35, 141.19 128.07, 127.51, 125.63, 120.56, 80.39, 65.80, 60.20, 47.17, 44.81, 28.13. Rt (10-100%): 23.5 min. ESI (m + Na): 448.1.
References
[1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 418 - 423
[2] Journal of the Chemical Society. Perkin Transactions 1, 2002, # 18, p. 2087 - 2089
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 7, p. 1691 - 1695
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 10, p. 2152 - 2158
[5] Synthesis, 1998, # 6, p. 837 - 841
Fmoc-L-beta-glutamic acid 5-tert-butyl ester Preparation Products And Raw materials
Raw materials
Preparation Products
Fmoc-L-beta-glutamic acid 5-tert-butyl ester Suppliers
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View Lastest Price from Fmoc-L-beta-glutamic acid 5-tert-butyl ester manufacturers
- Product
- Fmoc-beta-homo-Asp(OtBu)-OH 209252-17-5
- Price
- US $1780.00/g
- Min. Order
- 1g
- Purity
- 98
- Supply Ability
- 500 Kg
- Release date
- 2024-04-03
- Product
- Fmoc-L-beta-glutamic acid 5-tert-butyl ester 209252-17-5
- Price
- US $2.00/KG
- Min. Order
- 1g
- Purity
- 98%min
- Supply Ability
- ask
- Release date
- 2020-01-08