[ CAS No. 93206-09-8 ]

Name: 93206-09-8|2-(2-(Benzyloxy)ethoxy)acetic acid|98%
Brand: Ambeed
SKU: A586572
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{[proInfo.proName]} (Synonyms:BnO-PEG1-CH2COOH) ,{[proInfo.pro_purity]}

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Product Details of [ 93206-09-8 ]

CAS No. :	93206-09-8	MDL No. :
Formula :	-	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WEBYLMXBPGYVLS-UHFFFAOYSA-N
M.W :	-	Pubchem ID :	21790136
Synonyms :	BnO-PEG1-CH2COOH

Safety of [ 93206-09-8 ]

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Application In Synthesis of [ 93206-09-8 ]

* 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 [ 93206-09-8 ]

[ 93206-09-8 ] Synthesis Path-Downstream 1~25

1
[ 2050-25-1 ]
[ 93206-09-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 697 - 699

2
[ 70481-88-8 ]
[ 93206-09-8 ]
[ 93206-10-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 697 - 699

3
[ 3476-50-4 ]
[ 93206-09-8 ]
2-(2-Benzyloxy-ethoxy)-N-((S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamide [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1996,vol. 79,p. 2346 - 2352

4
[ 93206-09-8 ]
[ 181725-44-0 ]

Reference： [1]Synthesis,1996,p. 930 - 940

5
[ 622-08-2 ]
[ 79-11-8 ]
[ 93206-09-8 ]

Yield	Reaction Conditions	Operation in experiment
		(1) Sixty % sodium hydride in oil (6.80 g) is suspended in N,N-dimethylacetamide (80 ml) and a solution of 2-(benzyloxy)ethanol (12.9 g) in N,N-dimethylacetamide (50 ml) is added dropwise to the mixture over 10 minutes under ice-cooling. After stirring at room temperature for 15 minutes, the reaction solution is cooled with ice, and thereto is added chloroacetic acid (8.13 g) in small portions. The mixture is then stirred at room temperature for 11 hours. The reaction solution is concentrated under reduced pressure, and to the resulting residue is added aqueous sodium hydrogen carbonate solution and the mixture is washed with diethyl ether. The aqueous layer is acidified with conc. hydrochloric acid, and then extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove solvent under reduced pressure to give [2-(benzyloxy)ethoxy]acetic acid (18.24 g). ESI-MS M/Z:209[M-H]-

Reference： [1]Synthesis,1996,p. 930 - 940
[2]Patent: EP1666455,2006,A1 .Location in patent: Page/Page column 43-44

6
[ 93206-09-8 ]
[ 181725-46-2 ]

Reference： [1]Synthesis,1996,p. 930 - 940

7
[ 93206-09-8 ]
[ 181725-48-4 ]

Reference： [1]Synthesis,1996,p. 930 - 940

8
[ 93206-09-8 ]
[ 93206-12-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 697 - 699

9
[ 2216-51-5 ]
[ 93206-09-8 ]
(1R,2S,5R)-3-menthyl 7-phenyl-3,6-dioxaheptanoate [ No CAS ]

Reference： [1]Patent: US6359168,2002,B1 .Location in patent: Page column 6

10
[ 1068-52-6 ]
sodium 2-benzyloxyethanolate [ No CAS ]
[ 93206-09-8 ]

Reference： [1]Patent: US6359168,2002,B1 .Location in patent: Page column 6

11
[ 79-11-8 ]
[ 93206-09-8 ]

Yield	Reaction Conditions	Operation in experiment
		Sixty % sodium hydride in oil (6.80 g) is suspended in N,N-dimethylacetamide (80 ml) and a solution of 2-benzyloxyethanol (12.9 g) in N,N-dimethylacetamide (50 ml) is added dropwise to the mixture over a period of 10 minutes under ice-cooling. After stirring at room temperature for 15 minutes, the reaction solution is cooled with ice, thereto is added chloroacetic acid (8.13 g) gradually and the mixture is stirred at room temperature for 11 hours. The reaction solution is concentrated under reduced pressure, to the resulting residue is added aqueous sodium hydrogen carbonate solution and the mixture is washed with diethyl ether. The aqueous layer is acidified with conc. hydrochloric acid, and then extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove solvent under reduced pressure to give (2-benzyloxyethoxy)acetic acid (18.24 g). ESI-MS M/Z:209[M-H]-.
		(1) Sixty % sodium hydride in oil (6.80 g) is suspended in N,N-dimethylacetamide (80 ml) and a solution of 2-(benzyloxy)ethanol (12.9 g) in N,N-dimethylacetamide (50 ml) is added dropwise to the mixture over 10 minutes under ice-cooling. After stirring at room temperature for 15 minutes, the reaction solution is cooled with ice, and thereto is added chloroacetic acid (8.13 g) in small portions. The mixture is then stirred at room temperature for 11 hours. The reaction solution is concentrated under reduced pressure, and to the resulting residue is added aqueous sodium hydrogen carbonate solution and the mixture is washed with diethyl ether. The aqueous layer is acidified with conc. hydrochloric acid, and then extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove solvent under reduced pressure to give [2-(benzyloxy)ethoxy]acetic acid (18.24 g). ESI-MS M/Z:209[M-H]-.

Reference： [1]Patent: EP1489078,2004,A1 .Location in patent: Page 191
[2]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 118-119

12
E-4-aminocyclohexylcarboxylic acid methyl ester hydrochloride [ No CAS ]
[ 93206-09-8 ]
methyl trans-4-([2-(2-benzyloxy)ethoxy]acetyl}amino)-cyclohexanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 72h;	(2-Benzyloxyethoxy)acetic acid (6.51 g) obtained in (1), methyl trans-4-aminocyclohexanecarboxylate hydrochloride (5.27 g) obtained in Reference Example 113(1) and 1-hydroxybenzotriazole (5.06 g) are dissolved in N,N-dimethylformamide (100 ml). To the mixture are added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (7.10 g) and triethylamine (4.50 ml) successively under ice-cooling, and the mixture is stirred at room temperature for 3 days. The reaction solution is concentrated under reduced pressure, to the resulting residue is added an aqueous sodium hydrogen carbonate solution and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 1:1 followed' by ethyl acetate) to give methyl trans-4-[2-(2-benzyloxyethoxy)acetylamino]cyclohexanecarboxylate (8.24 g). APCI-MS M/Z:350[M+H]+.
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 72h;	[(2-Benzyloxy)ethoxy]acetic acid (6.51 g) obtained in (1) above, methyl trans-4-aminocyclohexane-carboxylate hydrochloride (5.27 g) obtained in Reference Example 2(1) and 1-hydroxybenzotriazole (5.06 g) are dissolved in N,N-dimethylformamide (100 ml). To the mixture are added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (7.10 g) and triethylamine (4.50 ml) successively under ice-cooling, and the mixture is stirred at room temperature for 3 days. The reaction solution is concentrated under reduced pressure, and to the resulting residue is added an aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 1:1 followed by ethyl acetate) to give methyl trans-4-([2-(2-benzyloxy)ethoxy]acetyl}amino)-cyclohexanecarboxylate (8.24 g). APCI-MS M/Z:350[M+H]+

Reference： [1]Patent: EP1489078,2004,A1 .Location in patent: Page 191
[2]Patent: EP1666455,2006,A1 .Location in patent: Page/Page column 44

13
[ 61367-07-5 ]
[ 93206-09-8 ]
[ 609805-64-3 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 72h;	(2) [(2-Benzyloxy)ethoxy]acetic acid (6.51 g) obtained in (1) above, <strong>[61367-07-5]methyl trans-4-aminocyclohexanecarboxylate hydrochloride</strong> (5.27 g) obtained in Reference Example 2(1) and 1-hydroxybenzotriazole (5.06 g) are dissolved in N,N-dimethylformamide (100 ml). To the mixture are added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (7.10 g) and triethylamine (4.50 ml) successively under ice-cooling, and the mixture is stirred at room temperature for 3 days. The reaction solution is concentrated under reduced pressure, and to the resulting residue is added an aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 1:1 followed by ethyl acetate) to give methyl trans-4-([2-(2-benzyloxy)ethoxy]acetyl}amino)cyclohexanecarboxylate (8.24 g). APCI-MS M/Z:350[M+H]+.

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 119

14
[ 29840-56-0 ]
[ 93206-09-8 ]
[ 727736-40-5 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 48h;	(1) Methyl 5-aminovalerate hydrochloride (3.35 g) obtained in Reference Example 6(1), [2-(benzyloxy)ethoxy]acetic acid (4.63 g) obtained in Reference Example 4(1) and 1-hydroxybenzotriazole (3.78 g) are dissolved in N,N-dimethylformamide (80 ml). To the mixture are added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.37 g) and triethylamine (3.35 ml) successively under ice-cooling, and the mixture is stirred at room temperature for 2 days. The reaction solution is concentrated under reduced pressure, and the resulting residue is diluted with ice-water and extracted with ethyl acetate. The organic layer is washed with aqueous sodium hydrogen carbonate solution, water and saturated brine successively, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 1:1 followed by ethyl acetate) to give methyl 5-([2-(benzyloxy)ethoxy]acetyl}amino)pentanoate (5.56 g). APCI-MS M/Z:324[M+H]+.
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 48h;	(1) Methyl 5-aminovalerate hydrochloride (3.35 g) obtained in Reference Example 6(1), [2-(benzyloxy)-ethoxy]acetic acid (4.63 g) obtained in Reference Example 4(1) and 1-hydroxybenzotriazole (3.78 g) are dissolved in N,N-dimethylformamide (80 ml). To the mixture are added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.37 g) and triethylamine (3.35 ml) successively under ice-cooling, and the mixture is stirred at room temperature for 2 days. The reaction solution is concentrated under reduced pressure, and the resulting residue is diluted with ice-water and extracted with ethyl acetate. The organic layer is washed with aqueous sodium hydrogen carbonate solution, water and saturated brine successively, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 1:1 followed by ethyl acetate) to give methyl 5-([2-(benzyloxy)ethoxy]acetyl}amino)pentanoate (5.56 g). APCI-MS M/Z:324[M+H]+

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 121
[2]Patent: EP1666455,2006,A1 .Location in patent: Page/Page column 46

15
2-N-[1,4,7-tris-(carboxylatomethyl)-1,4,7,10-tetraazacyclododecane-10-N-(pentanoyl-3-aza-4-oxo-5-methyl-5-yl)]-L-lysine-[(1H,1H,2H,2H-perfluorodecyl)-methyl]-amide, Gd complex [ No CAS ]
[ 93206-09-8 ]
C₄₇H₆₀F₁₇N₈O₁₂^(3-)*Gd⁽³⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 19h;	2.84 g (13.75 mmol) of dicyclohexylcarbodiimide is added at 0 C. to a solution of 12.75 g (10.0 mmol) of the title compound of Example 16b and 2.31 g (11.0 mmol) of <strong>[93206-09-8](2-benzyloxyethoxy)-acetic acid</strong> (Mitchell et al., Heterocyclic Chem., 1984, 697-699) and 1.27 g (11.0 mmol) of N-hydroxysuccinimide in 100 ml of dimethylformamide, it is stirred for 3 hours at 0 C. and then for 16 hours at room temperature. Precipitated urea is filtered out, and the filtrate is evaporated to the dry state in a vacuum. The residue is dissolved in 100 ml of methanol, mixed with 2.0 g of palladium catalyst (10% Pd/C) and hydrogenated for 24 hours at room temperature. Catalyst is filtered out, and the filtrate is evaporated to the dry state in a vacuum. The residue is taken up in a little water, insoluble components are filtered out, and the filtrate is then purified by chromatography (PP-18; mobile solvent: gradient that consists of water/acetonitrile). Yield: 9.7 g (68% of theory) of a colorless solid Water content (Karl-Fischer): 7.1% Elementary Analysis (relative to the anhydrous substance): Cld.: C 36.42 H 4.13 N 8.49 F 24.48 Gd 11.92 End.: C 36.61 H 4.17 N 8.44 F 24.39 Gd 11.87

Reference： [1]Patent: US2007/20183,2007,A1 .Location in patent: Page/Page column 32

16
[ 1192068-55-5 ]
[ 93206-09-8 ]
[ 1192068-65-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3652 - 3656

17
[ 869310-52-1 ]
[ 93206-09-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3652 - 3656

18
[ 1207632-14-1 ]
[ 93206-09-8 ]
[ 1207634-88-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 18h;	100. i-te^S-Fluoro^-methoxybenzyO-i^^.y-tetrahydro-SH-indolo^.S-cltiyinaphthyridin-3-yl]-2-(2-hydroxyethoxy)ethanone; Step 1 : 3-[2-(Benzyloxy)ethoxy]acetyl}-6-(3-fluoro-4-methoxybenzyl)-2,3,4,7-tetrahydro-1 H- indolo[2,3-c][1 ,7]naphthyridine. 6-(3-Fluoro-4-methoxybenzyl)-2,3,4,7-tetrahydro-1 H-indolo[2,3- c][1 ,7]naphthyridine (example 20) (200 mg) is suspended in dichloromethane (6 ml) and [2-(benzyloxy)ethoxy]acetic acid (example A10) (231 mg), 1-hydroxybenzotriazole (111 mg), 1-ethyl- 3-(3-dimethylaminopropyl)carbodiimide hydrochloride (210 mg) and triethylamine (354 μl) are added. The mixture is stirred for 18 h at room temperature. After that, water (10 ml) and dichloromethane (15 ml) are added, the aqueous phase is extracted with dichloromethane (2 x 15 ml), the combined organic extracts are dried (MgSO4) and concentrated in vacuo. The crude product is purified by column chromatography (silica gel, eluting with ethyl acetate / petroleum ether / triethylamine 5:5:1 (v/v/v)) to yield 260 mg (87%) of 3-[2-(benzyloxy)ethoxy]acetyl}-6-(3-fluoro-4- methoxybenzyl)-2,3,4,7-tetrahydro-1 H-indolo[2,3-c][1 ,7]naphthyridine as a colorless oil. 1H-NMR (300 MHz, d6-DMSO); δ = 3.30-3.41 , 3.49-3.60 (2m, 2H [rotamers]), 3.57-3.70 (m, 4H), 3.75 (s, 3H), 3.80-3.94 (m, 2H), 4.27-4.38 (m, 4H), 4.43, 4.50 (2s, 2H [rotamers]), 4.72-4.81 (m, 2H), 6.97-7.14 (m, 2H), 7.16-7.37 (m, 7H), 7.54 (dd, J = 7.8 Hz, 8.0 Hz, 1 H), 7.62 (d, J = 8.2 Hz, 1 H), 8.03, 8.16 (2d, J = 8.0 Hz, 1 H [rotamers]), 11.63 (s, 1 H). MS (MH+ found) = 554.3

Reference： [1]Patent: WO2010/15588,2010,A1 .Location in patent: Page/Page column 136

19
[ 124251-97-4 ]
[ 93206-09-8 ]

Yield	Reaction Conditions	Operation in experiment
93%		A10. [2-(Benzyloxy)ethoxy]acetic acid; Methyl [2-(benzyloxy)ethoxy]acetate (example A9) (2.50 g) is dissolved in dioxane (50 ml) and water (28 ml), lithium hydroxide (2.7 g) is added and the mixture is stirred for 1 h at 8O0C. After cooling, the mixture is acidified by addition of 6M hydrochloric acid, diluted with water (25 ml) and extracted with dichloromethane (3 x 50 ml). The combined organic extracts are washed with water (1 x 100 ml) and saturated sodium chloride solution (1 x 100 ml), dried (MgSO4) and concentrated in vacuo to give rise to 2.18 g (93%) of the title compound as a yellow oil. 1H-NMR (300 MHz, CDCI3); δ = 3.63-3.70 (m, 2H), 3.74-3.80 (m, 2H), 4.17 (s, 2H), 4.60 (s, 2H), 7.26-7.40 (m, 5H). MS (M+ found) = 210.2

Reference： [1]Patent: WO2010/15588,2010,A1 .Location in patent: Page/Page column 98

20
[ 1207516-29-7 ]
[ 93206-09-8 ]
[ 1207516-52-6 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 - 25℃; for 18h;	20. 1-[10-Fluoro-6-(3-fluoro-4-methoxybenzyl)-1,2,4,7-tetrahydro-3H-indolo[2,3- c][1,7]naphthyridin-3-yl]-2-(2-hydroxyethoxy)ethanoneStep 1 : 2-[2-(Benzyloxy)ethoxy]-1-[10-fluoro-6-(3-fluoro-4-methoxybenzyl)-1 ,2,4,7-tetrahydro-3H- indolo[2,3-c][1 ,7]naphthyridin-3-yl]ethanone. 10-Fluoro-6-(3-fluoro-4-methoxybenzyl)-2,3,4,7- tetrahydro-1 H-indolo[2,3-c][1 ,7]naphthyridine (example 10) (304 mg) is suspended in dichloromethane (10 ml) and [2-(benzyloxy)ethoxy]acetic acid (example A14) (336 mg), 1-hydroxybenzotriazole (184 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (306 mg) and triethylamine (296 μl) are added. The mixture is stirred for 18 h at room temperature. After that, water (15 ml) and dichloromethane (20 ml) are added, the aqueous phase is extracted with dichloromethane (2 x 20 ml), the combined organic extracts are dried (MgSO4) and concentrated in vacuo. The crude product, 2-[2- (benzyloxy)ethoxy]-1-[10-fluoro-6-(3-fluoro-4-methoxybenzyl)-1 ,2,4,7-tetrahydro-3H-indolo[2,3- c][1 ,7]naphthyridin-3-yl]ethanone, is used in the next step without further purification

Reference： [1]Patent: WO2010/15589,2010,A1 .Location in patent: Page/Page column 120

21
[ 93206-15-6 ]
[ 93206-09-8 ]

Yield	Reaction Conditions	Operation in experiment
		A14. [2-(Benzyloxy)ethoxy]acetic acidMethyl [2-(benzyloxy)ethoxy]acetate (example A13) (2.50 g) is dissolved in dioxane (50 ml) and water (28 ml), lithium hydroxide (2.7 g) is added and the mixture is stirred for 1 h at 8O0C. After cooling, the mixture is acidified by addition of 6M hydrochloric acid, diluted with water (25 ml) and extracted with dichloromethane (3 x 50 ml). The combined organic extracts are washed with water (1 x 100 ml) and saturated sodium chloride solution (1 x 100 ml), dried (MgSO4) and concentrated in vacuo to give rise to 2.18 g (93%) of the title compound as a yellow oil.1H-NMR (300 MHz, CDCI3); δ = 3.63-3.70 (m, 2H), 3.74-3.80 (m, 2H), 4.17 (s, 2H), 4.60 (s, 2H), 7.26-7.40 (m, 5H).MS (M+ found) = 210.2

Reference： [1]Bioconjugate Chemistry,2010,vol. 21,p. 1545 - 1553
[2]Patent: WO2010/15589,2010,A1 .Location in patent: Page/Page column 111-112

22
[ 622-08-2 ]
[ 93206-09-8 ]

Reference： [1]Patent: EP2332929,2011,A1
[2]Patent: WO2011/64300,2011,A1
[3]Bioconjugate Chemistry,2010,vol. 21,p. 1545 - 1553

23
[ 1309451-05-5 ]
[ 93206-09-8 ]
(3,9-dioxo-1-phenyl-2,5,8,11-tetraoxatridecan-13-yl) 2-(2-(benzyloxy)ethoxy)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%		3,9-dioxo-1-phenyl-2,5,8,11-tetraoxatridecan-13-yl 2-(2-(benzyloxy)ethoxy)acetate 11. To a stirred solution of triphenylphosphine (1.175 g, 4.48 mmol) in toluene (18 ml) at 0C was added DEAD (820 μl, 4.48 mmol). Mixture was stirred at 0C 10 min then a toluene solution (500 μl) of acid 10 (235 mg, 1.12 mmol) was added dropwise, followed by a toluene (500 μl) solution of alcohol 6 (350 mg, 1.12 mmol). Mixture was stirred 30 min et 0C and concentrated. Careful flash chromatography on silica gel (EtOAc/pentane 1/) afforded trimer 11 as an oil (273 mg, 48%). 1H NMR (CDCl3, 400 MHz): δ 7.36-7.31 (m, 5H), 5.17 (s, 2H), 4.55 (s, 2H), 4.35-4.29 (m, 4H), 4.21 (s, 2H), 4.16-4.12 (m, 4H), 3.78-3.73 (m, 6H), 3.68-3.63 (m, 2H).
48%	With diethylazodicarboxylate;triphenylphosphine; In toluene; at 0℃; for 0.5h;	3,9-dioxo-1 -phenyl-2, 5,8,11 -tetraoxatridecan-13-yl 2-(2- (benzyloxy)ethoxy)acetate 11. To a stirred solution of triphenylphosphine (1.175 g, 4.48 mmol) in toluene (18 ml) at15 0C was added DEAD (820 μΙ, 4.48 mmol). Mixture was stirred at 0C 10 min then a toluene solution (500 μΙ) of acid 10 (235 mg, 1.12 mmol) was added dropwise, followed by a toluene (500 μΙ) solution of alcohol 6 (350 mg, 1.12 mmol). Mixture was stirred 30 min et 0C and concentrated. Careful flash chromatography on silica gel (EtOAc/pentane 1/) afforded trimer 11 as an oil (273 mg, 48%).

Reference： [1]Patent: EP2332929,2011,A1 .Location in patent: Page/Page column 23-26
[2]Patent: WO2011/64300,2011,A1 .Location in patent: Page/Page column 37

24
[ 1309451-06-6 ]
[ 93206-09-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With trifluoroacetic acid; In dichloromethane; at 20℃; for 2h;	[2-(benzyloxy)ethoxy]acetic acid 10. To a stirred solution of ester 9 (2.66 g, 10 mmol) in dichloromethane (91 ml) was added TFA (9 ml). reaction mixture was stirred at room temperature for 2 hrs and mixture was concentrated. Obtained residue was diluted in water and basified with a NaOH 1 N solution. This aqueous layer was extracted with ether then acidified and extracted twice with EtOAc. Combined organic layers were dried over MgSO4, filtered and concentrated to give acid 10 (2 g, 95%) as an oil, used for next step without further purification.
95%		Ο,Η [2-(benzyloxy)ethoxy]acetic acid 10. To a stirred solution of ester 9 (2.66 g, 10BnOmmol) in dichloromethane (91 ml) was added TFA (9 ml), reaction mixture was stirred at room temperature for 2 hrs and mixture was concentrated. Obtained residue was diluted in water and basified with a NaOH 1 N solution. This aqueous layer was extracted with ether then acidified and extracted twice with EtOAc. Combined organic layers were dried over MgS04, filtered and concentrated to give acid 10 (2 g, 95%) as an oil, used for next step without further purification.

Reference： [1]Patent: EP2332929,2011,A1 .Location in patent: Page/Page column 23-25
[2]Patent: WO2011/64300,2011,A1 .Location in patent: Page/Page column 37

25
[ 93206-09-8 ]
[ 109-76-2 ]
[ 1239890-95-9 ]

Reference： [1]Bioconjugate Chemistry,2010,vol. 21,p. 1545 - 1553

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Carboxylic Acids

[ 91842-53-4 ]

2-(2-(2-(Benzyloxy)ethoxy)ethoxy)acetic acid

Similarity: 1.00

[ 30379-55-6 ]

2-(Benzyloxy)acetic acid

Similarity: 1.00

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 93206-09-8 ]

Quality Control of [ 93206-09-8 ]

Related Doc. of [ 93206-09-8 ]

Product Details of [ 93206-09-8 ]

Safety of [ 93206-09-8 ]

Application In Synthesis of [ 93206-09-8 ]

[ 93206-09-8 ] Synthesis Path-Downstream 1~25

Related Functional Groups of [ 93206-09-8 ]

Aryls

Ethers

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 93206-09-8 ]