(S)-N-Fmoc-Allylglycine

Product Name: (S)-N-Fmoc-Allylglycine
CAS No.: 146549-21-5
Chemical Name: (S)-N-Fmoc-Allylglycine
Synonyms: Fmoc-L-ALG;FMOC-ALGLY-OH;Fmoc-Allyglycine;N-FMOC protected;FMOC-GLY(ALLYL)-OH;FMOC-(ALLYL)GLY-OH;Fmoc-L-Allyglycine;RARECHEM BK PT 0251;FMoc-a-allyl-Gly-OH;FMOC-L-ALLYLGLYCINE
CBNumber: CB8362146
Molecular Formula: C20H19NO4
Formula Weight: 337.37
MOL File: 146549-21-5.mol

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(S)-N-Fmoc-Allylglycine Property

Melting point:: 137.1 °C
Boiling point:: 473.68°C (rough estimate)
Density: 1.2486 (rough estimate)
refractive index: 1.5800 (estimate)
storage temp.: 2-8°C
solubility: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 3.72±0.10(Predicted)
color: White to Off-White
optical activity: -8.633° (C=0.01 g/ml, DMF)
Water Solubility: Slightly soluble in water.
InChI: InChI=1S/C20H19NO4/c1-2-7-18(19(22)23)21-20(24)25-12-17-15-10-5-3-8-13(15)14-9-4-6-11-16(14)17/h2-6,8-11,17-18H,1,7,12H2,(H,21,24)(H,22,23)/t18-/m0/s1
InChIKey: YVBLQCANYSFEBN-SFHVURJKSA-N
SMILES: C(O)(=O)[C@@H](NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O)CC=C
CAS DataBase Reference: 146549-21-5(CAS DataBase Reference)

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Safety

Hazard Codes: Xi
Safety Statements: 24/25
WGK Germany: 3
HazardClass: IRRITANT
HS Code: 29242990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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

Sigma-Aldrich

Product number: 00347
Product name: Fmoc-allyl-Gly-OH
Purity: ≥98.0% (HPLC)
Packaging: 1 g
Price: $186.9
Updated: 2025/07/31

TRC

Product number: F603520
Product name: Fmoc-L-allylglycine
Packaging: 100mg
Price: $45
Updated: 2021/12/16

Usbiological

Product number: 276784
Product name: FMoc-L-Allylglycine
Packaging: 1g
Price: $651
Updated: 2021/12/16

SynQuest Laboratories

Product number: 4958-1-05
Product name: L-2-Allylglycine, N-Fmoc protected
Packaging: 10g
Price: $656
Updated: 2021/12/16

Activate Scientific

Product number: AS88430
Product name: Fmoc-(S)-2-Allylglycine
Purity: 95% ee
Packaging: 25g
Price: $827
Updated: 2021/12/16

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(S)-N-Fmoc-Allylglycine Chemical Properties,Usage,Production

Chemical Properties

white to almost white powder

Uses

2-Allyl-N-Fmoc-L-glycine is potentially useful for solid phase peptide synthesis techniques. 2-Allyl-N-Fmoc-L-glycine compound could be useful as an unusual amino acid analog to aid in the deconvolution of protein structure and function. Reagent in the synthesis of a Dicarba-Analog of Octreotide.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

16338-48-0

82911-69-1

146549-21-5

The general procedure for the synthesis of Fmoc-L-allylglycine from (S)-(-)-2-amino-4-pentenoic acid and 9-fluorenylmethyl-N-succinimidyl carbonate is as follows: 7.14.1 Preparation of 2-N-fluorenylmethoxycarbonylaminopent-4-enoic acid (Fmoc-Hag-OH) Allylglycine derivatives were prepared according to Paquet's method. Fmoc-OSu (14.60 g, 43.3 mmol) was added to a solution of L-allylglycine (5.00 g, 43.5 mmol) and NaHCO3 (18.20 g, 0.22 mol) in acetone:water (200 mL) mixture under stirring conditions. The resulting white suspension was stirred at room temperature for 20 h. Complete consumption of the raw material was confirmed by thin layer chromatography (TLC, silica gel plate, light petroleum ether:ethyl acetate = 1:1) analysis. The reaction mixture was acidified to pH 2 with concentrated hydrochloric acid and acetone was removed under reduced pressure. The resulting suspension was extracted with dichloromethane (DCM, 3×75 mL), and the organic phases were combined, washed sequentially with dilute hydrochloric acid (1M, 2×50 mL), water (2×50 mL), dried (MgSO4), and concentrated under reduced pressure to afford the target product Fmoc-amino acid 96 as a colorless solid (14.01 g, 96% yield) with a melting point of 137-138 °C (literature value (134-136°C). IR spectrum (KBr, cm-1): 3484 (s), 3198 (bs), 3085 (m), 2967 (m), 2923 (m), 1723 (s), 1644 (m), 1525 (s), 1478 (w), 1449 (s), 1396 (m), 1340 (m), 1233 (s), 1189 (s). 1099(m), 1048(s), 998(w), 966(w), 943(m), 924(w), 850(m), 781(m), 761(s), 740(m), 648(w), 623(m), 582(m), 560(w), 540(m), 424(w). 1H NMR (400MHz, CDCl3): δ 2.52-2.70 (m, 2H, H3), 4.23 (t, J=6.9Hz, 1H, H9'), 4.42 (d, J=6.9Hz, 2H, CH2O), 4.52 (m, 1H, H2), 5.13-5.23 (m, 2H, H5), 5.31 (bd, J= 7.8 Hz, 1H, NH), 5.75 (m, 1H, H4), 6.63 (bs, 1H, OH), 7.31 (td, J=7.4,0.8 Hz, 2H, H2',7'), 7.38 (t, J=7.4 Hz, 2H, H3',6'), 7.52-7.63 (m, 2H, H1',8'), 7.76 (d, J = 7.5 Hz, 2H, H4',5'), no exchangeable protons (OH) were observed. 13C NMR (100 MHz, CDCl3): δ 36.7 (C3), 47.5 (C9'), 53.4 (C2), 68.1 (CH2O), 122.0 (C5), 120.1 (C2',7'), 125.4 (C3',6'), 127.9 (C1',8'), 128.0 (C4',5') 131.1 (C4), 141.7 (C8'a,9'a), 144.0 (C4'a,4'b), 156.3 (OCONH), 176.4 (C1). Mass spectrum (ESI+, MeOH): m/z 338.4 ([M+H]+, calculated value 338.1, C20H20NO4), 360.3 ([M+Na]+, calculated value 360.1, C20H19NNaO4). The spectral data are in agreement with those reported in the literature.

References

[1] Patent: US9102708, 2015, B2. Location in patent: Page/Page column 151
[2] Organic Letters, 2004, vol. 6, # 19, p. 3285 - 3288
[3] Tetrahedron, 2014, vol. 70, # 42, p. 7621 - 7626

(S)-N-Fmoc-Allylglycine Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-N-Fmoc-Allylglycine Suppliers

Belgium 1 China 150 Europe 1 France 1 Germany 4 India 4 Japan 2 South Korea 1 Switzerland 1 United Kingdom 5 United States 28 Global 198

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View Lastest Price from (S)-N-Fmoc-Allylglycine manufacturers

Career Henan Chemical Co

Product: (S)-N-Fmoc-Allylglycine 146549-21-5
Price: US $7.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: JD 387
Release date: 2019-09-01

146549-21-5, (S)-N-Fmoc-AllylglycineRelated Search:

Allyl hexanoate 4-Aminophenylacetic acid Allyl chloride Allyl bromide Allyl glycidyl ether Fmoc-Lys(Boc)-OH 4-Hydroxy-D-(-)-2-phenylglycine 6-Aminocaproic acid Glycine METHOXYCARBONYLSULFENYL CHLORIDE Sodium allylsulfonate L-Fmoc-Aspartic acid alpha-tert-butyl ester Sodium glycinate 9-Fluorenylmethyl chloroformate 2-Aminophenol Tris(hydroxymethyl)aminomethane Fmoc-OSu Fmoc-Asp(OtBu)-OH

Fmoc-Allyglycine

FMOC-L-2-allylglycine Hydrochloride

2-Allyl-N-FMoc-L-glycine, 95%

FMoc-L-Allyglycine FMoc-L-Allyglycine

(S)-2-FMoc-aMino-4-pentenoic acid, FMoc-L-allylglycine

FMoc-a-allyl-Gly-OH

(S)-2-(((9H-fluoren-9-yl)Methoxy)carbonylaMino)pent-4-enoic acid

FMoc-(S)-2-Allylglycine

N-Fmoc-allyl-L-glycine

Fmoc-allyl-L-glycine≥ 99% (HPLC, Chiral purity)

RARECHEM BK PT 0251

(S)-N-(9-FLUORENYLMETHOXYCARBONYL)-2-AMINO-4-PENTENOIC ACID

(S)-N-FMOC-ALLYLGLYCINE

(S)-FMOC-ALLYLGLYCINE

(S)-2-(FMOC-AMINO)-4-PENTENOIC ACID

N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-L-ALPHA-ALLYL-GLYCINE

FMOC-(S)-2-AMINO-4-PENTENOIC ACID

FMOC-L-ALLYLGLYCINE

FMOC-L-2-ALLYLGLYCINE

FMOC-GLY(ALLYL)-OH

FMOC-ALGLY-OH

Fmoc-L-Gly(allyl)-OH

N-FMOC protected

Fmoc-L-ALG

2-[[9H-fluoren-9-ylmethoxy(oxo)methyl]-prop-2-enylamino]acetic acid

L-2-Allylglycine, N-FMOC protected 97%

Fmoc-2-allyl-L-glycine

FMOC-(ALLYL)GLY-OH

FMOC-ALLYL-L-GLYCINE

FMOC-ALPHA-ALLYL-L-GLY

Fmoc-L-Alpha-Allyl-Gly

Fmoc-L-Allyglycine

(S)-N-fmoc-Allylglycine(e.e.)

N-Fluorenemethoxycarbonyl-L-Allyl Glycine

L-2-Allylglycine, N-FMOC protected

(S)-N-FMOC-ALLYLGLYCINE 98%

(S)-2-(Fmoc-amino)-4-pentenoic acid, Fmoc-L-2-allylglycine

(9H-Fluoren-9-yl)MethOxy]Carbonyl L-Gly(Allyl)-OH

(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pent-4-enoic acid

(S)-N-FMOC-ALLYLGLYCINE, 95%, 98% EE

(S)-N-FMOC-Allylglycine, 98% ee

4-Pentenoic acid, 2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (2S)-

2-Allyl-N-Fmoc-L-glycine,95%

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)pent-4-enoicaci

(S)-N-Fmoc-Allylglycine USP/EP/BP

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)pent-4-e

Fmoc-L-Allylglycine CAS

Fmoc-allyl-Gly-OH 98%

146549-21-5

C20H20N04

Glycine Derivatives

Peptide Synthesis

Specialty Synthesis

Unnatural Amino Acid Derivatives

Unusual amino acids

a-amino

Amino Acids

unnatural amino acids