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Quality Control of Propargyl-PEG4-Tos Purity: 98% SDS Specification

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Product Details of Propargyl-PEG4-Tos

CAS No. :	875770-32-4
Formula :	C₁₈H₂₆O₇S
M.W :	386.46
SMILES Code :	C#CCOCCOCCOCCOCCOS(C1=CC=C(C)C=C1)(=O)=O
Synonyms :	Propargyl-PEG4-Tos
MDL No. :	MFCD28950765
Boiling Point :	No data available
InChI Key :	VUJIUZITHCTEAF-UHFFFAOYSA-N
Pubchem ID :	87060474

Safety of Propargyl-PEG4-Tos

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of Propargyl-PEG4-Tos

* 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 [ 875770-32-4 ]

[ 875770-32-4 ] Synthesis Path-Downstream 1~35

1
[ 875770-32-4 ]
4,4-difluoro-8-(4-aminophenyl)-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene [ No CAS ]
[ 1198404-10-2 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 6383 - 6388.

2
[ 37860-51-8 ]
[ 107-19-7 ]
[ 875770-32-4 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 6383 - 6388.

3
[ 875770-32-4 ]
[ 1236153-17-5 ]
[ 1236153-18-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium carbonate; In acetonitrile; at 60℃; for 24h;	To acetonitrile (5 mL) were added 16 ( 0.070 g, 0.24 mmol), O- propargyl-tetraethyene glycol tosylate 18 (0.125 g, 0.32 mmol), and potassium carbonate (0.140 g, 1.0 mmol). The reaction mixture was heated at 60ºC with stirring for 24 h, cooled to ambient temperature, filtered and the filtrate was evaporated to dryness. The residue was purified by column chromatography on silica gel using methanol-dichloromethane (2:98) as the eluent. [0200] The product was isolated as a colorless oil (0.75 g, 0.15 mmol, 60%). Method B. 'H-NMR(CD3COCD3):8.90(bs, 1H, NH); 8.58(s, 1H, C2-H); 8.00( dt, 1H, C2-H); 7.68(s, 1H, C5-H); 7.57( d, 1H, C6 -H); 7.34(q,1H, C4-H); 7.20(s, 1H, C8-H); 6.83(t, 1H, C5-H); 4.3 l(t, 2H); 4.16(d, 2H,J=2.5 Hz);3.92(s, 3H); 3.70-3.50 (m, 14H), 2.92(t; 1H, J= 2.5Hz).
60%	With potassium carbonate; In acetonitrile; at 60℃; for 24h;	Method A. To a solution of 16 (0.40 g, 1.4 mmol), 17 (0.40 g, 1.7 mmol) and triphenylphospine (0.45 g, 1.7 mmol) in 30 mL dichloromethane was added slowly, with stirring, a solution of diisopropyl azodicarboxylate (0.35 g, 1.7 mmol) in 10 mL dichloromethane. The resultant solution was stirred at ambient temperature for 16 h, evaporated to dryness, and the resultant residue was separated by column chromatography on silica gel using a step gradient from 1% to 5% methanol in dichloromethane. The product was isolated as a colorless oil (0.27 g, 0.54 mmol, 38%). Method B. To acetonitrile (5 mL) were added 16 ( 0.070 g, 0.24 mmol), O-propargyl-tetraethyene glycol tosylate 18 (0.125 g, 0.32 mmol), and potassium carbonate (0.140 g, 1.0 mmol). The reaction mixture was heated at 60C with stirring for 24h, cooled to ambient temperature, filtered and the filtrate was evaporated to dryness. The residue was purified by column chromatography on silica gel using methanol-dichloromethane (2:98) as the eluent. The product was isolated as a colorless oil (0.75 g, 0.15 mmol, 60%). Method B. 1H-NMR(CD3COCD3):8.90(bs, 1H, NH); 8.58(s, 1H, C2-H); 8.00( dt, 1H, C2’-H); 7.68(s, 1H, C5-H); 7.57( d, 1H, C6’-H); 7.34(q,1H, C4’-H); 7.20(s, 1H, C8-H); 6.83(t, 1H, C5’-H); 4.31(t, 2H); 4.16(d, 2H,J=2.5 Hz);3.92(s, 3H); 3.70-3.50 (m, 14H), 2.92(t, 1H, J= 2.5Hz).

References: [1]Patent: WO2010/85747,2010,A1 .Location in patent: Page/Page column 59.
[2]Tetrahedron Letters,2011,vol. 52,p. 1053 - 1056.

4
[ 875770-32-4 ]
[ 1240167-40-1 ]
[ 1259292-34-6 ]

References: [1]Organic Letters,2011,vol. 13,p. 438 - 441.

5
[ 98-59-9 ]
[ 87450-10-0 ]
[ 875770-32-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With triethylamine; In dichloromethane; at 20℃;Inert atmosphere;	A homogeneous solution of L-5-1 (10.98 g, 47.27 mmol) in dry DCM at room temperature under N2 atmosphere was treated with TEA (17.13 mL, 122.90 mmol), p- TsCl (18.02 g, 94.54 mmol) and stirred to room temperature overnight. The reaction mixture was concentrated in vacuo. The residue was purified by flash chromatography (EA : HEX = 1 : 3 to 1 : 1) to give the title compound: L-5-2 (17.06 g, 93 %) as a liquid.NMR (400 MHz, CDCb) S 7.79-7.77 (m, 2H), 7.33-7.30 (m, 2H), 4.20-4.10 (m, 4H), 3.71-3.55 (m, 14H), 2.43-2.40 (m, 4H).
86%	With triethylamine; In dichloromethane; at 0 - 20℃;	To a solution of compound 26 (2.7 g, 11.6 mmol) in dichloromethane (5 mL), was added triethylamine (3.2 mL, 23.2 mmol). The resulted mixture was cooled to 0C. To the mixture, tosyl chloride (2.33 g, 12.2 mmol) was added. The resulted mixture was allowed to warm to room temperature and stirred at room temperature overnight. To the mixture, water (10 mL) was added. The resulted mixture was extracted with dichloromethane (3 x 10 mL). The organic layer was washed with 6 N HC1 (15 mL), water (10 mL), sodium bicarbonate (5%, 10 mL) and brine (10 mL), dried over magnesium sulfate and concentrated in vacuum. The residue was submitted to purification with column chromatography using silica gel and solvent system from dichloromethane to 2/98 (v/v) methanol/dichloromethane, affording compound 27 as a colorless oil (3.83 g, 86%).
76%	With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;Inert atmosphere;	SI (0.8 g, 3.44 mmol) and triethylamine (1.440 ml, 10.33 mmol) were dissolved in CH2CI2 (6mL) and cooled down to 0C. A solution of tosyl chloride (0.788 g, 4.13 mmol) in CH2CI2 (3mL) was then added to the cooled solution. The reaction was then allowed to warm up to room temperature and stirred for l6h. The reaction was quenched with saturated aqueous NH4CI. The mixture was extracted with CH2CI2, washed with 1M HC1, water, and brine, respectively. The organic phase was then dried over anhydrous Na2S04, filtered and concentrated to dryness. The crude mixture was purified with silica gel column chromatography. The product was obtained as clear colorless viscous liquid (l.Olg, 76%).1H-NMR (400 MHz, Chloroform-ri) d 7.79 (d , J= 8.3 Hz, 2H), 7.33 (dt, J= 7.9, 0.7 Hz, 2H), 4.18 (d, J= 2.4 Hz, 2H), 4.16 - 4.12 (m, 2H), 3.71 - 3.60 (m, 10H), 3.57 (s, 4H), 2.44 (s, 3H), 2.42 (t, J= 2.4 Hz, 1H). HPLC-MS calcd for C18H27O7S [M+H]+ 387.15 found 387.37

32%

With pyridine; In dichloromethane; at 0 - 20℃;

Into a 100-mL 3-necked round-bottom flask, was placed a solution of 266a.0 (2 g, 8.19 mmol, 1.00 equiv, 95%) in dichloromethane (10 mL), pyridine (15 mL). This was followed by the addition of 4-methylbenzene-1-sulfonyl chloride (3.27 g, 17.21 mmol, 2.00 equiv), in portions at 0-10 C. The resulting solution was stirred overnight at room temperature. The resulting solution was diluted with 200 mL of ethyl acetate. The resulting mixture was washed with 1*30 mL of water and 2*30 mL of 10% hydrogen chloride. The resulting mixture was washed with 1*30 mL of sodium bicarbonate and 1*30 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). This resulted in 1.2 g (32%) of 2-(2-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate as light brown oil.

References: [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 4461 - 4468.
[2]Patent: WO2021/111185,2021,A1 .Location in patent: Page/Page column 48.
[3]Bioconjugate Chemistry,2012,vol. 23,p. 785 - 795.
[4]Chemical Communications,2022,vol. 58,p. 3338 - 3341.
[5]Chemical Communications,2022,vol. 58,p. 3945 - 3948.
[6]Dalton Transactions,2011,vol. 40,p. 12052 - 12055.
[7]Organic and Biomolecular Chemistry,2016,vol. 14,p. 3120 - 3129.
[8]Journal of Medicinal Chemistry,2018,vol. 61,p. 453 - 461.
[9]Patent: WO2021/141984,2021,A1 .Location in patent: Page/Page column 30-31; 44.
[10]Molecular Pharmaceutics,2015,vol. 12,p. 4414 - 4423.
[11]Angewandte Chemie - International Edition,2017,vol. 56,p. 8771 - 8775.
Angew. Chem.,2017,vol. 129,p. 8897 - 8901.
[12]Cell Chemical Biology,2019,vol. 26,p. 1229 - 9,1239.
[13]Patent: WO2020/76849,2020,A1 .Location in patent: Paragraph 00151-00152-00153.
[14]Chemistry - A European Journal,2018,vol. 24,p. 16085 - 16096.
[15]European Journal of Organic Chemistry,2021,vol. 2021,p. 1763 - 1767.
[16]Journal of labelled compounds and radiopharmaceuticals,2011,vol. 54,p. 693 - 701.
[17]Organic and Biomolecular Chemistry,2011,vol. 9,p. 8465 - 8474.
[18]Patent: US9301951,2016,B2 .Location in patent: Page/Page column 592.
[19]Organic Letters,2011,vol. 13,p. 438 - 441.
[20]Medicinal Chemistry,2011,vol. 7,p. 45 - 55.
[21]ChemBioChem,2018,vol. 19,p. 1969 - 1978.
[22]Molecules,2022,vol. 27.

6
[ 875770-32-4 ]
[ 1308299-11-7 ]