| Identification | More | [Name]
(R)-N-BOC-Propargylglycine | [CAS]
63039-46-3 | [Synonyms]
BOC-D-PROPARGYLGLYCINE
RARECHEM BK PT 0259
(R)-N-BOC-PROPARGYLGLYCINE
(R)-N-TERT-BUTOXYCARBONYL-2-AMINO-4-PENTYNOIC ACID
(R)-N-(TERT-BUTOXYCARBONYL)-PROPARGYLGLYCINE
Boc-D-Gly(propargyl)-OH
(R)-N-boc-Propargylglycine(e.e.)
N-TERT-BUTOXYCARBONYL-D-PROPARGYL GLYCINE
N-BOC-2-PROPARGYL-D-GLYCINE
BOC-2-PROPARGYL-D-GLYCINOL
D-2-Propargylglycine, N-BOC protected
(R)-(1-Hydroxymethyl-but-3-ynyl)-carbamic acid tert-butyl ester
(R)-2-tert-Butoxycarbonylamino-pent-4-ynoic acid
Boc-D-Propargylglycine.DCHA
(R)-N-BOC-PROPARGYLGLYCINE, 95%, 98% EE
(R)-N-BOC-Propargylglycine, 98% ee | [Molecular Formula]
C10H15NO4 | [MDL Number]
MFCD01320886 | [Molecular Weight]
213.23 | [MOL File]
63039-46-3.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to light beige crystalline powder | [Melting point ]
86-88° | [Boiling point ]
353.22°C (rough estimate) | [density ]
1.2177 (rough estimate) | [refractive index ]
1.4368 (estimate) | [storage temp. ]
2-8°C | [form ]
Crystalline Powder | [pka]
3.53±0.10(Predicted) | [color ]
Off-white to light beige | [Optical Rotation]
-32.6364°(C=1.1311 g/100ml CHCL3) | [InChI]
InChI=1S/C10H15NO4/c1-5-6-7(8(12)13)11-9(14)15-10(2,3)4/h1,7H,6H2,2-4H3,(H,11,14)(H,12,13)/t7-/m1/s1 | [InChIKey]
AMKHAJIFPHJYMH-SSDOTTSWSA-N | [SMILES]
C(O)(=O)[C@H](NC(OC(C)(C)C)=O)CC#C | [CAS DataBase Reference]
63039-46-3(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
off-white to light beige crystalline powder | [Uses]
(R)-2-((tert-Butoxycarbonyl)amino)pent-4-ynoic acid is a Glycine (HY-Y0966) derivative[1]. (R)-2-((tert-Butoxycarbonyl)amino)pent-4-ynoic acid is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. | [Synthesis]
Step 5: Preparation of (R)-2-((tert-butoxycarbonyl)amino)pent-4-ynoic acid
L-alkynylglycine (10 g) [prepared according to Schwyzer et al, Helv. Chim. Acta, 59, 2181 (1976)] was suspended in tetrahydrofuran (30 mL). To this suspension, water (30 mL), potassium carbonate (36.7 g) and di-tert-butyl dicarbonate (21.9 g) were added sequentially. Subsequently, additional water was added to completely dissolve the mixture and the resulting solution was stirred for 12 hours at room temperature. Upon completion of the reaction, the organic solvent was removed by evaporation. The remaining aqueous phase was washed with ether and then acidified with 1N aqueous citric acid to pH 3. The acidified aqueous phase was extracted with dichloromethane, and the organic phases were combined and the solvent was removed by evaporation to afford (R)-2-((tert-butoxycarbonyl)amino)pent-4-ynoic acid (18.9 g, 97% yield), and the product was ready to use in subsequent reactions without further purification. | [References]
[1] Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144. DOI:10.1080/10408398.2012.708368 |
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