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Chemical Structure| 29248-48-4 Chemical Structure| 29248-48-4

Structure of Boc-Gly-Gly-OSU
CAS No.: 29248-48-4

Chemical Structure| 29248-48-4

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Product Details of [ 29248-48-4 ]

CAS No. :29248-48-4
Formula : C13H19N3O7
M.W : 329.31
SMILES Code : O=C(ON1C(CCC1=O)=O)CNC(CNC(OC(C)(C)C)=O)=O
MDL No. :MFCD00190796
InChI Key :KMFADWSLCJBFMN-UHFFFAOYSA-N
Pubchem ID :11244365

Safety of [ 29248-48-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 29248-48-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 29248-48-4 ]

[ 29248-48-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 39987-25-2 ]
  • [ 29248-48-4 ]
  • [2-(2-tert-butoxycarbonylamino-acetylamino)-acetyl]-methoxycarbonylmethyl-amino}-acetic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With triethylamine; In N,N-dimethyl-formamide; at 20℃; To a stirred solution of <strong>[39987-25-2](methoxycarbonylmethyl-amino)-acetic acid methyl ester hydrochloride</strong> (8) (988 mg, 5 mmol) in DMF (15 ml) were added Boc-GlyGlyNos (3) (3293 mg, 10 mmol) and (CH3CH2)3N (3475 muL, 25 mmol) were added. The mixture was stirred overnight at room temperature and then diluted with o-xylene (70 ml) and evaporated. (0184) Flash column chromatography on silica gel (packed in toluene, and eluted with ethyl acetate) resulted in a crude product. (0185) The crude product was dissolved in chloroform and washed sequentially with water, 0.5 M NaHCO3 and saturated KCl. (0186) The chloroform extract was evaporated and the product purified on a silica gel column (packed in chloroform and eluted with 15:1 (v/v) chloroform/methanol). Evaporation of the fractions and drying under vacuum of the residue provided a colourless thick syrup of (9). Yield 1785 mg, (95%). TLC: Rf=0.49 (7:1 (v/v) chloroform/methanol). (0187) 1H NMR (500 MHz, [D6]DMSO, 30 C.) delta, ppm: 7.826 (t, J=5.1 Hz, 1H; NHCO), 6.979 (t, J=5.9 Hz, 1H; NHCOO), 4.348 and 4.095 (s, 2H; NCH2COO), 3.969 (d, J=5.1 Hz, 2H; COCH2NH), 3.689 and 3.621 (s, 3H; OCH3), 3.559 (d, J=5.9 Hz, 2H; COCH2NHCOO). 1.380 (s, 9H; C(CH3)3).
95% With triethylamine; In N,N-dimethyl-formamide; at 20℃; To a stirred solution of (methoxycarbonylmethyl-amino ) -acetic acid methyl ester hydrochloride (988 mg, 5 mmol) in DMF (15 ml) were added Boc-GlyGlyNos (3293 mg, 10 mmol) and (CH3CH2) 3N (3475 mu,, 25 mmol) were added. The mixture was stirred overnight at room temperature and then diluted with o-xylene (70 ml) and evaporated. Flash column chromatography on silica gel (packed in toluene, and eluted with ethyl acetate) resulted in a crude product. The crude product was dissolved in chloroform and washed sequentially with water, 0.5 M NaHCC and saturated KC1. The chloroform extract was evaporated and the product purified on a silica gel column (packed in chloroform and eluted with 15:1 (v/v) chloroform/methanol ) . Evaporation of the fractions and drying under vacuum of the residue provided a colourless thick syrup. Yield 1785 mg, (95%) . TLC: Rf=0.49 (7:1 (v/v) chloroform/methanol ) . NMR (500 MHz, [D6]DMSO, 30 C) delta, ppm: 7.826 (t, J"=5.1 Hz, 1H; NHCO), 6.979 (t, J=5.9 Hz, 1H; NHCOO), 4.348 and 4.095 (s, 2H; NCH2COO) , 3.969 (d, J=5.1 Hz, 2H; COCH2NH) , 3.689 and 3.621 (s, 3H; OCH3) , 3.559 (d, J=5.9 Hz, 2H; COCH2NHCOO) , 1.380 (s, 9H; C(CH3)3)
95% With triethylamine; In N,N-dimethyl-formamide; at 20℃; Preparation of [2-(2-tert-butoxycarbonylamino-acetylamino)-acetyl]-methoxycarbonylmethyl-amino}-acetic acid methyl ester (SCHEME I) (0117) To a stirred solution of <strong>[39987-25-2](methoxycarbonylmethyl-amino)-acetic acid methyl ester hydrochloride</strong> (988 mag, 5 mmol) in DMF (15 ml) were added Boc-GlyGlyNos (3293 mg, 10 mmol) and (CH3CH2)3N (3475 muL, 25 mmol) were added. The mixture was stirred overnight at room temperature and then diluted with o-xylene (70 ml) and evaporated. (0118) Flash column chromatography on silica gel (packed in toluene, and eluted with ethyl acetate) resulted in a crude product. The crude product was dissolved in chloroform and washed sequentially with water, 0.5 M NaHCO3. and saturated KCl. (0119) The chloroform extract was evaporated and the product purified on a silica gel column (packed in chloroform and eluted with 15:1 (v/v) chloroform/methanol). Evaporation of the fractions and drying under vacuum of the residue provided a colourless thick syrup. Yield 1785 mg, (95%). TLC: Rf=0.49 (7:1 (v/v) chloroform/methanol). 1H NMR (500 MHz, [D6]DMSO, 30 C) delta, ppm: 7.826 (t, J=5.1 Hz, 1H; NHCO), 6.979 (t, J=5.9 Hz, 1H; NHCOO), 4.348 and 4.095 (s, 2H; NCH2COO), 3.969 (d, J=5.1 Hz, 2H; COCH2NH), 3.689 and 3.621 (s, 3H; OCH3), 3.559 (d, J=5.9,Hz, 2H; COCH2NHCOO), 1.380 (s, 9H; C(CH3)3).
95% With triethylamine; In N,N-dimethyl-formamide; at 20℃; To a stirred solution of (methoxycarbonylmethyl-amino ) -acetic acid methyl ester hydrochloride (988 mg, 5 mmol) in DMF (15 ml) were added Foc-GlyGlyNos (3293 mg, 10 mmol) and (CH3CH2)3N (3475 pL, 25 mmol) were added. The mixture was stirred overnight at room temperature and then diluted with o-xylene (70 ml) and evaporated. Flash column chromatography on silica gel (packed in toluene and eluted with ethyl acetate) resulted in a crude product. The crude product was dissolved in chloroform and washed sequentially with water, 0.5 M NaHC03 and saturated KC1. The chloroform extract was evaporated and the product purified on a silica gel column (packed in chloroform and eluted with 15:1 (v/v) chloroform/methanol) . Evaporation of the fractions and drying under vacuum of the residue provided a colourless thick syrup. Yield 1785 mg, (95%) . TLC: Rf=0.49 (7:1 (v/v) chloroform/methanol) . NMR (500 MHz, [D6]DMSO, 30 C) d, ppm: 7.826 (t, J=5.1 Hz, 1H; NHCO), 6.979 (t, J=5.9 Hz, 1H; NHCOO), 4.348 and 4.095 (s, 2H; NCH2COO) , 3.969 (d, J=5.1 Hz, 2H; COCH2NH) , 3.689 and 3.621 (s, 3H; OCH3) , 3.559 (d, J=5.9 Hz, 2H; COCHzNHCOO) , 1.380 (s, 9H; C(CH3)3) ·

 

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