14464-29-0|2,5-Dioxopyrrolidin-1-yl acetate| Ambeed

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Quality Control of [ 14464-29-0 ] Purity: 98% SDS Specification

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Product Details of [ 14464-29-0 ]

CAS No. :	14464-29-0
Formula :	C₆H₇NO₄
M.W :	157.12
SMILES Code :	CC(=O)ON1C(=O)CCC1=O
MDL No. :	MFCD00037916
InChI Key :	SIFCHNIAAPMMKG-UHFFFAOYSA-N
Pubchem ID :	84460

Safety of [ 14464-29-0 ]

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

Application In Synthesis of [ 14464-29-0 ]

* 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.

Upstream synthesis route of [ 14464-29-0 ]
Downstream synthetic route of [ 14464-29-0 ]

[ 14464-29-0 ] Synthesis Path-Upstream 1~1

1
[ 14464-29-0 ]
[ 692-04-6 ]

References: [1] Patent: CN109265371, 2019, A, . Location in patent: Paragraph 0026-0028.

[ 14464-29-0 ] Synthesis Path-Downstream 1~35

1
[ 6066-82-6 ]
[ 64-19-7 ]
[ 14464-29-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With dicyclohexyl-carbodiimide; In 1,4-dioxane; at 5 - 20℃; for 20h;	2.2 ml (25 mmol) DCCD was added at 5C to a solution of 1.43 ml (25 mmol) acetic acid and 2.2 ml (0.25 mmol)N-hydroxysuccinimide in 50 ml dioxane. The reaction mixture was stirred at 20C for 20 h. The resulting precipitate wasfiltered off and washed with dry dioxane. The filtrates were combined and evaporated to yield 3.65 g (93%) of the productas white crystals. Rf 0.41 (C), Rf 0.75 (I); m.p. 103-105C. 1H NMR (DMSO-d6): 2.34 (3H, s, -CH3CO-), 2.80 (4H, m, -CH2CH2- OSu).
	With 1,2-dichloro-ethane; In dichloromethane; for 3h;	General procedure: To a stirred solution of appropriate acid 44a-f (1.96mmol) in CH2Cl2 (3mL) were added NHS (0.361g, 3.14mmol) and EDC (0.601g, 3.14mmol). After 3h, the mixture was diluted with CH2Cl2 (40mL). The organic layer was washed with brine (2×40mL), saturated aqueous NaHCO3 (40mL) and brine (2×40mL), dried over Na2SO4, filtered and concentrated to give NHS activated esters (80-100% yield) that were used immediately without further purification.
	With dicyclohexyl-carbodiimide; In ethyl acetate; at 20℃;Inert atmosphere;	The syntheses of GlcNAc and GlcNGc from glucosamine were based on the method described by Lapidot [31]. The procedure for the synthesis of GlcNAc was performed as follows: acetic acid (0.286 mL, 5 mmol) was added to a solution of N-hydroxysuccinimide (0.575 g, 5 mmol) in dry ethyl acetate (23 mL). A solution of dicyclohexylcarbodiimide (1.03 g, 5 mmol) in ethyl acetate (2 mL)was then added. The reaction mixture was stirred at room temperature overnight under a nitrogen atmosphere. Then, the precipitate of the reaction mixture was removed by centrifugation at 13,400 g for 10 min. The supernatant contained an NHS-ester of acetic acid was dried by rotary evaporation under reduced pressure and re-dissolved in dry 17 mL of methanol. D-Glucosamine hydrochloride(0.862 g, 4 mmol) and triethylamine (0.56 mL) were then added and dissolved by placing the sample ina heated sonication bath (50 C for 1 h). The reaction mixture was then stirred at room temperature for 16 h. The sample was again dried using rotary evaporation and washed three times with ethyl acetate(1 mL) to remove the unreacted starting material. After vacuum drying of the sample using centrifugal evaporation, the product was dissolved in 8 mL of 10% methanol in water (v/v). The supernatant was collected and concentrated using a rotary evaporator under reduced pressure. For the synthesisof GlcNGc, glycolic acid (0.3 mL, 5 mmol) was used instead of acetic acid. As judged by TLC analysis, the conversion of D-glucosamine to the reaction products 4a or 4b reached approximately 70%. These amidated reaction products were then used directly as starting material for the enzymatic sialylation reactions.

References: [1]Patent: EP2397488,2019,B1 .Location in patent: Paragraph 0181; 0182.
[2]Journal of the Chemical Society. Chemical communications,1985,p. 473.
[3]Journal of Medicinal Chemistry,2000,vol. 43,p. 2938 - 2945.
[4]Tetrahedron,1998,vol. 54,p. 3489 - 3494.
[5]Journal of Molecular Structure,1992,vol. 273,p. 215 - 226.
[6]European Journal of Medicinal Chemistry,2017,vol. 138,p. 13 - 25.
[7]Molecules,2019,vol. 24.

2
[ 6066-82-6 ]
[ 75-36-5 ]
[ 14464-29-0 ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 146 - 151.
[2]Tetrahedron,1997,vol. 53,p. 15225 - 15236.

3
[ 14464-29-0 ]
[ 2037-48-1 ]
[ 51587-80-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 2186 - 2208.

4
[ 14464-29-0 ]
[ 1078691-95-8 ]
N-acetylglucosamine-6-phosphate barium salt [ No CAS ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 146 - 151.

5
[ 14464-29-0 ]
C₁₈H₂₈N₄O₇S [ No CAS ]
[ 121903-84-2 ]
[ 129624-97-1 ]

References: [1]Tetrahedron,1990,vol. 46,p. 3813 - 3818.

6
[ 14464-29-0 ]
[ 121903-84-2 ]
(4-Acetylamino-butyl)-[2-(5-{2-[2-(2,4-bis-benzyloxy-phenyl)-acetylamino]-3-carbamoyl-propionylamino}-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester [ No CAS ]

References: [1]Tetrahedron,1990,vol. 46,p. 3813 - 3818.

7
[ 14464-29-0 ]
H-Gly-Pro-Leu-Gly-NHOBzl*HCl [ No CAS ]
[ 137022-70-9 ]

References: [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1489 - 1494.

8
[ 14464-29-0 ]
[ 81035-27-0 ]
[ 81035-48-5 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 373 - 381.

9
[ 14464-29-0 ]
[ 76494-20-7 ]
[ 76381-69-6 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 304 - 308.

10
[ 14464-29-0 ]
[ 96760-69-9 ]
[ 96760-70-2 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1341 - 1346.

11
[ 14464-29-0 ]
Val-Leu-Arg(Adoc)2 [ No CAS ]
[ 99029-53-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 529 - 536.

12
[ 14464-29-0 ]
[ 117823-00-4 ]
[ 114138-80-6 ]

References: [1]Tetrahedron,1988,vol. 44,p. 877 - 886.

13
[ 14464-29-0 ]
2'-O-(N-carbobenzoxy-L-phenylalanyl)-pCpA [ No CAS ]
2'-O-(N-acetyl-L-phenylalanyl)-pCpA [ No CAS ]

References: [1]Tetrahedron,1984,vol. 40,p. 87 - 94.

14
[ 14464-29-0 ]
[ 81035-06-5 ]
[ 81035-47-4 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 373 - 381.

15
[ 14464-29-0 ]
[ 137848-39-6 ]
[ 108320-87-2 ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 152 - 157.

16
[ 14464-29-0 ]
[ 144874-16-8 ]
[ 144874-18-0 ]

References: [1]Tetrahedron Letters,1992,vol. 33,p. 5791 - 5794.

17
[ 14464-29-0 ]
[ 144874-17-9 ]
[ 144874-19-1 ]

References: [1]Tetrahedron Letters,1992,vol. 33,p. 5791 - 5794.

18
[ 14464-29-0 ]
(3R,6S,9R,12S,15S)-15-Amino-12-((S)-sec-butyl)-6-isobutyl-9-methyl-5,8,11,14-tetraoxo-1-thia-4,7,10,13-tetraaza-cyclohexadecane-3-carboxylic acid methylamide [ No CAS ]
[ 120841-21-6 ]

References: [1]Journal of the American Chemical Society,1992,vol. 114,p. 5634 - 5642.

19
[ 14464-29-0 ]
(3R,6S,9S,12S,15S)-15-Amino-12-((S)-sec-butyl)-6-isobutyl-9-methyl-5,8,11,14-tetraoxo-1-thia-4,7,10,13-tetraaza-cyclohexadecane-3-carboxylic acid methylamide [ No CAS ]
[ 120841-20-5 ]

References: [1]Journal of the American Chemical Society,1992,vol. 114,p. 5634 - 5642.

20
[ 14464-29-0 ]
[ 96865-92-8 ]
[ 96896-78-5 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1334 - 1340.

21
[ 14464-29-0 ]
C₉H₁₈N₆O₅*ClH [ No CAS ]
[ 85917-93-7 ]