[ CAS No. 4344-84-7 ] {[proInfo.proName]}

Name: 4344-84-7|5-Oxotetrahydrofuran-2-carboxylic acid|95%
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SKU: A156433
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Quality Control of [ 4344-84-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 4344-84-7 ]

Product Details of [ 4344-84-7 ]

CAS No. :	4344-84-7	MDL No. :	MFCD00066678
Formula :	C₅H₆O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	130.10	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 4344-84-7 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.6
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	27.09
TPSA :	63.6 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.41
Log Po/w (XLOGP3) :	-0.19
Log Po/w (WLOGP) :	-0.22
Log Po/w (MLOGP) :	-0.52
Log Po/w (SILICOS-IT) :	0.24
Consensus Log Po/w :	-0.06

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-0.46
Solubility :	45.0 mg/ml ; 0.346 mol/l
Class :	Very soluble
Log S (Ali) :	-0.69
Solubility :	26.6 mg/ml ; 0.204 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.28
Solubility :	246.0 mg/ml ; 1.89 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.16

Safety of [ 4344-84-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4344-84-7 ]

* 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 [ 4344-84-7 ]
Downstream synthetic route of [ 4344-84-7 ]

[ 4344-84-7 ] Synthesis Path-Upstream 1~18

1
[ 4344-84-7 ]
[ 7664-41-7 ]
[ 5626-52-8 ]

Reference： [1] Nippon Kagaku Zasshi, 1959, vol. 80, p. 1317,1320[2] Chem.Abstr., 1961, p. 4358

2
[ 4344-84-7 ]
[ 19365-07-2 ]

Reference： [1] Patent: CN106748972, 2017, A,

3
[ 617-65-2 ]
[ 4344-84-7 ]

Yield	Reaction Conditions	Operation in experiment
104 g	With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 0.25 h; Inert atmosphere	(1) at room temperature and under N2 protection,140 ml of concentrated hydrochloric acid was added to a solution of 270 mL of H2O as a solvent in Compound 1 (2-aminoglutaric acid)There is an exothermic phenomenon,After the system becomes clear, the system cools down to 0 ° C.At 0 ° C,To the system was slowly added 70.3 g of NaNO2 H2O solution (200 mL)There is temperature,The system becomes green and turbid.15min after the drop is completed, T = 2 ,Maintain 0 ° C reaction.Solution system directly at 50 under the oil pump concentrated dry,The concentrated dry system was beaten with 400 mL of ethyl acetate,Filtration, filter cake continued with 400mL ethyl acetate beating once,The filter cake was rinsed with 200 mL of ethyl acetate, the filtrates were combined,45 ° C pump to dry to obtain 104 g of a yellow oily liquid (compound 2).

Reference： [1] Chemische Berichte, 1961, vol. 94, p. 2106 - 2114
[2] Chemistry and Industry (London, United Kingdom), 1959, p. 1413
[3] Justus Liebigs Annalen der Chemie, 1890, vol. 260, p. 128
[4] Patent: CN106748972, 2017, A, . Location in patent: Paragraph 0022; 0023; 0024; 0030

4
[ 105-53-3 ]
[ 503-11-7 ]
[ 4344-84-7 ]

Yield	Reaction Conditions	Operation in experiment
11 g	Stage #1: With sodium ethanolate In ethanol for 2 h; Reflux; Inert atmosphere Stage #2: With sodium hydroxide In ethanol; water at 50℃; for 1 h; Stage #3: With hydrogenchloride In ethanol; water	In a 500 mL reaction flask equipped with a stirrer, 8.8 g of carboxycyclopropyl ether and 16.6 mg of diethyl malonate were added, 6.8 g (0.1 mol) of sodium ethoxide and 100 mL of ethanol were added, and the mixture was heated to reflux under a nitrogen atmosphere. 2h after the reaction was cooled to room temperature, slowly added sodium hydroxide dissolved in 2g of 20mL aqueous solution, warmed to 50 ° C for 1h; The solution was slowly cooled to 0 ° C and the diluted hydrochloric acid solution was slowly added dropwise to adjust the pH of the reaction solution to 5. The reaction solution was extracted with 200 mL of ethyl acetate for three times. The combined organic phases were concentrated to give 11 g of β-carboxy-γ-butyrolactone.

Reference： [1] Patent: CN106589027, 2017, A, . Location in patent: Paragraph 0030; 0033; 0034; 0035; 0036; 0037; 0038

5
[ 328-50-7 ]
[ 110-94-1 ]
[ 4344-84-7 ]
[ 2889-31-8 ]

Reference： [1] Green Chemistry, 2017, vol. 19, # 8, p. 1866 - 1876

6
[ 328-50-7 ]
[ 4344-84-7 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986, p. 1565 - 1580

7
[ 56-86-0 ]
[ 4344-84-7 ]
[ 2889-31-8 ]

Reference： [1] Phytochemical Analysis, 2012, vol. 23, # 1, p. 60 - 71

8
[ 56-85-9 ]
[ 4344-84-7 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1989, # 1, p. 88 - 94

9
[ 56-86-0 ]
[ 4344-84-7 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1989, # 1, p. 88 - 94

10
[ 27025-41-8 ]
[ 4344-84-7 ]
[ 7729-20-6 ]
[ 125347-31-1 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1989, # 1, p. 88 - 94

11
[ 2889-31-8 ]
[ 4344-84-7 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1890, vol. 260, p. 128
[2] Helvetica Chimica Acta, 1919, vol. 2, p. 449

12
[ 56-85-9 ]
[ 4344-84-7 ]

Reference： [1] Chemische Berichte, 1961, vol. 94, p. 2106 - 2114
[2] Chemistry and Industry (London, United Kingdom), 1959, p. 1413

13
[ 117889-07-3 ]
[ 4344-84-7 ]

Reference： [1] Nippon Kagaku Zasshi, 1959, vol. 80, p. 647,648[2] Chem.Abstr., 1961, p. 3426

14
[ 117889-07-3 ]
[ 4344-84-7 ]
[ 27620-83-3 ]

Reference： [1] Nippon Kagaku Zasshi, 1959, vol. 80, p. 1317,1320[2] Chem.Abstr., 1961, p. 4358

15
[ 4189-03-1 ]
[ 7664-41-7 ]
[ 4344-84-7 ]

Reference： [1] Nippon Kagaku Zasshi, 1959, vol. 80, p. 1317,1320[2] Chem.Abstr., 1961, p. 4358

16
[ 7209-05-4 ]
[ 7664-41-7 ]
[ 4344-84-7 ]
[ 617-65-2 ]

Reference： [1] Nippon Kagaku Zasshi, 1959, vol. 80, p. 1317,1320[2] Chem.Abstr., 1961, p. 4358

17
[ 4344-84-7 ]
[ 52065-78-8 ]

Reference： [1] Patent: CN106748972, 2017, A,

18
[ 67-56-1 ]
[ 4344-84-7 ]
[ 3885-29-8 ]
[ 81077-10-3 ]
[ 1119-40-0 ]

Reference： [1] Green Chemistry, 2017, vol. 19, # 8, p. 1866 - 1876

[ 4344-84-7 ] Synthesis Path-Downstream 1~88

1
[ 117889-07-3 ]
[ 4344-84-7 ]

Reference： [1]Nippon Kagaku Zasshi,1959,vol. 80,p. 647,648
Chem.Abstr.,1961,p. 3426

2
[ 117889-07-3 ]
[ 4344-84-7 ]
[ 27620-83-3 ]

Reference： [1]Nippon Kagaku Zasshi,1959,vol. 80,p. 1317,1320
Chem.Abstr.,1961,p. 4358

4
[ 4344-84-7 ]
[ 617-65-2 ]

Reference： [1]Nippon Kagaku Zasshi,1959,vol. 80,p. 1317,1320
Chem.Abstr.,1961,p. 4358
[2]Nippon Kagaku Zasshi,1956,vol. 77,p. 401
Chem.Abstr.,1958,p. 257

6
[ 617-65-2 ]
[ 4344-84-7 ]

Yield	Reaction Conditions	Operation in experiment
104 g	With hydrogenchloride; sodium nitrite; In water; at 0 - 20℃; for 0.25h;Inert atmosphere;	(1) at room temperature and under N2 protection,140 ml of concentrated hydrochloric acid was added to a solution of 270 mL of H2O as a solvent in Compound 1 (2-aminoglutaric acid)There is an exothermic phenomenon,After the system becomes clear, the system cools down to 0 ° C.At 0 ° C,To the system was slowly added 70.3 g of NaNO2 H2O solution (200 mL)There is temperature,The system becomes green and turbid.15min after the drop is completed, T = 2 ,Maintain 0 ° C reaction.Solution system directly at 50 under the oil pump concentrated dry,The concentrated dry system was beaten with 400 mL of ethyl acetate,Filtration, filter cake continued with 400mL ethyl acetate beating once,The filter cake was rinsed with 200 mL of ethyl acetate, the filtrates were combined,45 ° C pump to dry to obtain 104 g of a yellow oily liquid (compound 2).

Reference： [1]Chemische Berichte,1961,vol. 94,p. 2106 - 2114
[2]Justus Liebigs Annalen der Chemie,1890,vol. 260,p. 128
[3]Patent: CN106748972,2017,A .Location in patent: Paragraph 0022; 0023; 0024; 0030

7
[ 2889-31-8 ]
[ 4344-84-7 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1890,vol. 260,p. 128
[2]Helvetica Chimica Acta,1919,vol. 2,p. 449

8
1-bromo-propane-1,1,3-tricarboxylic acid [ No CAS ]
[ 4344-84-7 ]

Reference： [1]Journal of Organic Chemistry,1938,vol. 3,p. 200

9
[ 4344-84-7 ]
[ 106-41-2 ]
[ 111075-15-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1986,p. 1565 - 1580

10
[ 4344-84-7 ]
[ 75-05-8 ]
[ 65758-34-1 ]
[ 497-23-4 ]

Reference： [1]Chemische Berichte,1983,vol. 116,p. 375 - 388

11
[ 4344-84-7 ]
[ 75-05-8 ]
[ 65758-34-1 ]
[ 497-23-4 ]
1-acetyl-2H,3H-pyrrol-2-one [ No CAS ]

Reference： [1]Chemische Berichte,1983,vol. 116,p. 375 - 388

12
[ 4344-84-7 ]
[ 106-40-1 ]
[ 111075-16-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1986,p. 1565 - 1580

13
[ 4344-84-7 ]
[ 20825-71-2 ]
[ 65758-34-1 ]
[ 497-23-4 ]

Reference： [1]Chemische Berichte,1983,vol. 116,p. 375 - 388

14
[ 328-50-7 ]
[ 4344-84-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1986,p. 1565 - 1580

15
[ 56-85-9 ]
[ 4344-84-7 ]

Reference： [1]Bulletin de la Societe Chimique de France,1989,p. 88 - 94

16
[ 56-86-0 ]
[ 4344-84-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium nitrite; In water; at -5 - 15℃; for 12h;	To a solution of 2-aminopentanedioic acid (210 g, 1.43 mol, CAS617-65-2) in H2O (800 mL) and HCl (12 M, 210 mL) was added a solution of NaNO2 (147 g, 2.13 mol) in H2O (400 mL) at -5 C. The mixture was stirred at 15 C. for 12 hrs. On completion, the mixture was concentrated and then dissolved in EA (500 mL) and filtered and washed with EA (3×100 mL). The filtrate and washed solution were dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (200 g, crude) as yellow oil. 1H NMR (400 MHz, CDCl3) delta 6.43 (s, 1H), 5.02-4.95 (m, 1H), 2.67-2.38 (m, 4H)

Reference： [1]Bulletin de la Societe Chimique de France,1989,p. 88 - 94
[2]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 2977; 2978

17
[ 4344-84-7 ]
[ 65057-35-4 ]
[ 65057-44-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 1667 - 1672
[2]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 1667 - 1672

18
[ 4344-84-7 ]
[ 104159-76-4 ]
Blc-3-Me-His-Pro-NH₂ [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 1667 - 1672
[2]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 1667 - 1672

19
[ 4344-84-7 ]
[ 95729-81-0 ]
[ 65057-45-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 1667 - 1672
[2]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 1667 - 1672

20
[ 4344-84-7 ]
H-His-ProNHPhEt [ No CAS ]
[ 65057-46-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 1667 - 1672
[2]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 1667 - 1672

21
[ 4344-84-7 ]
[ 33605-69-5 ]
[ 63836-94-2 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 1667 - 1672
[2]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 1667 - 1672

22
[ 4344-84-7 ]
[ 82977-45-5 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃;	Step 2: 5-Oxo-tetrahydro-furan-2-carboxylic acid (5-methyl-pyridin-2-yl)-amide; Oxalyl chloride (0.252 g, 1.63 mmol) in DCM (5 mL) was added slowly to a stirred solution of 5-oxotetrahydrofuran-2-carboxylic acid (Step 1) (0.215 g, 1.65 mmol) in DCM (10 ml) and DMF (50 mul) at 0° C. After 3 hrs at ambient temperature, gas evolution had subsided. DIPEA (0.64, 4.95 mmol) was added followed by the addition of 2-amino-5-picoline (0.357 g, 3.3 mmol) in DCM (5 mL). The reaction mixture was kept at ambient temperature for 3 hrs. Water (0.5 mL) was added and the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluting with a gradient consisting of 0-40percent MeOH in DCM) to give the title compound as a colorless oil (0.138 g). 1H NMR (500 MHz, CDCl3) delta 8.74 (br s, 1H), 8.13 (d, 1H), 8.08 (d, 1H), 7.54 (dd, 1H), 4.99 (t, 1H), 2.71 (m, 1H), 2.63 (m, 2H), 2.48 (m, 1H), 2.31 (s, 3H).
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; for 2h;Cooling with ice;	5-Oxo-2-tetrahydrofuran carboxylic acid (1.77 g, 13.6 mmol) was dissolved in CH2C12 (8 mL). DMF (30 uL) was added, and the solution cooled in an ice bath.Oxalyl chloride (2.97 mL, 34 mmol) was added dropwise over 20 min. The ice bath was then removed, and the reaction mixture was stirred for 2 h. The solvent was removed, and the residue crude 5-oxo-2-tetrahydrofuran carbonyl chloride was used in step 2.

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 2111 - 2122
[2]Patent: US2010/93757,2010,A1 .Location in patent: Page/Page column 121
[3]Patent: WO2012/135084,2012,A1 .Location in patent: Page/Page column 21

23
[ 4344-84-7 ]
[ 51268-87-2 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

24
[ 4344-84-7 ]
[ 171335-60-7 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

25
[ 4344-84-7 ]
[ 158010-31-2 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

26
[ 4344-84-7 ]
[ 158110-04-4 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

27
[ 4344-84-7 ]
[ 404936-42-1 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

28
[ 4344-84-7 ]
[ 404936-43-2 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

29
[ 4344-84-7 ]
[ 404936-44-3 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

30
[ 4344-84-7 ]
[ 404936-46-5 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

31
[ 4344-84-7 ]
[ 404936-47-6 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

32
[ 4344-84-7 ]
[ 404936-45-4 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

33
[ 4344-84-7 ]
[ 404936-52-3 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

34
[ 4344-84-7 ]
(1S,11S,13R)-11-(3-Benzyloxy-propyl)-7-methoxy-10,17-dioxa-tricyclo[11.3.1.0^3,8]heptadeca-3,5,7-trien-9-one [ No CAS ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

35
[ 4344-84-7 ]
[ 404936-41-0 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

36
[ 4344-84-7 ]
[ 404936-50-1 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

37
[ 4344-84-7 ]
[ 404936-49-8 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

38
[ 4344-84-7 ]
[ 404936-51-2 ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

39
[ 4344-84-7 ]
(1S,2S,11S,13R)-11-(3-Benzyloxy-propyl)-7-methoxy-2-phenylselanyl-10,17-dioxa-tricyclo[11.3.1.0^3,8]heptadeca-3,5,7-trien-9-one [ No CAS ]

Reference： [1]Organic letters,2002,vol. 4,p. 643 - 646

40
[ 4344-84-7 ]
3-[4-Methoxycarbonylmethyl-5-methyl-1-(5-oxo-tetrahydro-furan-2-carbonyl)-1H-pyrrol-3-yl]-propionic acid methyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 2111 - 2122

41
[ 4344-84-7 ]
[ 194421-66-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 2111 - 2122

42
[ 4344-84-7 ]
[ 194421-78-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 2111 - 2122

43
[ 4344-84-7 ]
4-(2-Methoxycarbonylethyl)-3-methoxycarbonylmethyl-5-(5-oxotetrahydrofuran-2-yl)formylpyrrole-2-carboxylic acid [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 2111 - 2122

44
[ 4344-84-7 ]
5-Acetoxymethyl-3-(2-methoxycarbonylethyl)-4-methoxycarbonylmethyl-2-(5-oxotetrahydrofuran-2-yl)formylpyrrole [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 2111 - 2122

45
[ 4344-84-7 ]
N-((5S)-3-(4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide, trifluoroacetic salt [ No CAS ]
C₂₃H₂₇N₃O₅ [ No CAS ]

Reference： [1]Patent: US6365751,2002,B1 .Location in patent: Example 87

46
[ 4344-84-7 ]
[ 55714-67-5 ]
[ 108050-21-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; sodium hydrogencarbonate; In dichloromethane;	REFERENCE EXAMPLE 8 Production of 1-t-butyl 2-oxoglutarate [Compound (8)] To a solution of 5.0 g of 5-oxo-2-tetrahydrofurancarboxylic acid in 100 ml of dichloromethane was added 0.3 ml of concentrated sulfuric acid, to which was further added an excess volume (ca. 50 ml) of isobutene. The reaction mixture was left standing overnight at room temperature under tight sealing, which was poured into a cooled saturated aqueous solution of sodium hydrogencarbonate. The dichloromethane layer was separated, washed with water, dried (Na2 SO4) and concentrated to give t-butyl 5-oxo-2-tetrahydrofurancarboxylate as a colorless oily substance. IRnumaxNeat cm-1: 1760. NMR (60 MHz, CDCl3)delta: 1.50(9H, s), 2.4(4H, m), 4.8(1H, m).

Reference： [1]Patent: US4891427,1990,A

47
[ 4344-84-7 ]
[ 55714-67-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium bicarbonate; sulfuric acid; In dichloromethane;	EXAMPLE 41 Production of 1-t-butyl 2-oxoglutarate [Compound (41)]: In 100 ml of dichloromethane was dissolved 5.0 g of 5-oxo-2-tetrahydrofurancarboxylic acid. To the solution was added 0.3 ml of concentrated sulfuric acid at -60° C., to which was added an excess volume of isobutene (about 50 ml). The reaction mixture was allowed to stand at room temperature overnight in a sealed vessel, which was then poured into a cooled aqueous solution of sodium hydrogen carbonate. The dichloromethane layer was taken, washed with water and dried (Na2 SO4), followed by concentration to give t-butyl 5-oxo-2-tetrahydrofurancarboxylate as colorless oil. IRnumaxNeat cm-1: 1760NMR(60 MHz, CDCl3)delta: 1.50(9H,s),2.4(4H,m),4.8(1H,m)

Reference： [1]Patent: US4851422,1989,A

48
[ 4344-84-7 ]
[ 2835-77-0 ]
2-(5-oxotetrahydrofuran-2-carbonyl)aminobenzophenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; sodium hydrogencarbonate; In ethyl acetate;	(1) 2-(5-Oxotetrahydrofuran-2-carbonyl)aminobenzophenone A mixture of 4.9 g of 5-oxotetrahydrofuran-2-carboxylic acid and 5.5 ml of thionyl chloride was subjected to reflux for 2 hours. Thionyl chloride was then distilled off under reduced pressure to leave 5-oxotetrahydrofuran-2-carbonyl chloride. This product was mixed with 5.0 g of 2-aminobenzophenone, 200 ml of ethyl acetate and 200 ml of a saturated aqueous solution of sodium hydrogencarbonate, which was stirred for one hour at room temperature. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to give 2-(5-oxotetrahydrofuran-2-carbonyl)aminobenzophenone (6.5 g) as needles, m.p. 100° C.-102° C. IRnumaxKBr cm-1: 3300(NH) 1790, 1690, 1640(C=O) Elemental Analysis for C18 H15 NO4: Calcd.: C 69.89; H 4.88; N 4.53 Found: C 69.98; H 5.01; N 4.41

Reference： [1]Patent: US5726306,1998,A

49
[ 4344-84-7 ]
[ 14243-64-2 ]
[ 916737-26-3 ]

Reference： [1]Inorganic Chemistry Communications,2006,vol. 9,p. 355 - 359

50
α-hydroxyglutaric acid zinc salt [ No CAS ]
[ 4344-84-7 ]

Yield	Reaction Conditions	Operation in experiment
	With Amberlite(R) IR-120; In tetrahydrofuran; at 20℃; for 16h;	Step 1: 5-oxotetrahydrofuran-2-carboxylic acid; Amberlite(R) IR-120 (3.0 g, washed with 4.x.20 ml THF) was added to a stirred suspension of alpha-hydroxyglutaric acid zinc salt (0.40 g, 1.90 mmol) in THF (15 mL). The reaction mixture was kept at ambient temperature for 16 hrs. The reaction mixture was filtered and the resin was washed three times with THF. The combined extracts was concentrated in vacuo and the residue was purified by column chromatography (silica gel, eluting with a gradient consisting of 5-50percent MeOH in DCM) to give the title compound as a colorless oil (0.215 g). 1H NMR (500 MHz, D2O) delta 5.00 (t, 1H), 2.53 (m, 3H), 2.20 (m, 1H).

Reference： [1]Patent: US2010/93757,2010,A1 .Location in patent: Page/Page column 121

51
[ 56-86-0 ]
[ 4344-84-7 ]
[ 2889-31-8 ]

Reference： [1]Phytochemical Analysis,2012,vol. 23,p. 60 - 71

52
[ 4344-84-7 ]
[ 1402054-40-3 ]

Reference： [1]Patent: WO2012/135084,2012,A1

53
[ 67-56-1 ]
[ 4344-84-7 ]
[ 3885-29-8 ]
[ 81077-10-3 ]
[ 1119-40-0 ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 1866 - 1876

54
[ 328-50-7 ]
[ 110-94-1 ]
[ 4344-84-7 ]
[ 2889-31-8 ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 1866 - 1876

55
[ 4344-84-7 ]
(5-oxotetrahydrofuran-2-yl)methyl methanesulfonate [ No CAS ]

Reference： [1]Patent: CN106748972,2017,A

56
[ 4344-84-7 ]
[ 179532-81-1 ]

Reference： [1]Patent: CN106748972,2017,A

57
[ 4344-84-7 ]
[ 19365-07-2 ]

Reference： [1]Patent: CN106748972,2017,A

58
[ 4344-84-7 ]
[ 110-94-1 ]

Yield	Reaction Conditions	Operation in experiment
40%	With palladium 10% on activated carbon; W(OTf)6; hydrogen; acetic acid; at 150℃; under 15001.5 Torr; for 12h;	General procedure: Specific methods are as follows: propiolactone was added (0.36g, 5mmol), palladium on carbon (10percent, 26.5mg, 0.025mmol, 0.5molpercent) in the reactor and W (OTf)6(107.8mg, 0.1mmol, 2molpercent). A hydrogen balloon connected to the top of the reactor, and the reactor was purged with hydrogen gas atmosphere. Hydrogen atmosphere at normal pressure, the reaction was stirred at 135 deg.] C after 12h, detected by gas, gamma- valerolactone complete conversion of starting material, and only n-valeric acid. The method carried out as follows completion of the hydrogenation reaction of the ring-opening reaction system separation, to obtain the desired product n-valeric acid: The reaction was completed reaction mixture was dissolved with methylene chloride, filtered to remove the palladium on carbon catalyst and W (OTf)699percent yield measured propionic acid, purity of the product was 99percent. NMR data for the product using the embodiment of the present invention is the NMR identified the product as follows:The specific reaction procedure and operation method were the same as in Example 27 except that the substrate used was 2 mmol, And add lmL of acetic acid as solvent, the reaction temperature is 150 ° C, the hydrogen pressure is 2MPa, the yield is 40percent The purity of the product is 99percent. The product was subjected to nuclear magnetic identification using the manner described in the present invention, The NMR data for the product are as follows:

Reference： [1]Patent: CN106831389,2017,A .Location in patent: Paragraph 0113; 0231-0233
[2]ACS Catalysis,2017,vol. 7,p. 7520 - 7528

59
[ 105-53-3 ]
[ 503-11-7 ]
[ 4344-84-7 ]

Yield	Reaction Conditions	Operation in experiment
11 g		In a 500 mL reaction flask equipped with a stirrer, 8.8 g of carboxycyclopropyl ether and 16.6 mg of diethyl malonate were added, 6.8 g (0.1 mol) of sodium ethoxide and 100 mL of ethanol were added, and the mixture was heated to reflux under a nitrogen atmosphere. 2h after the reaction was cooled to room temperature, slowly added sodium hydroxide dissolved in 2g of 20mL aqueous solution, warmed to 50 ° C for 1h; The solution was slowly cooled to 0 ° C and the diluted hydrochloric acid solution was slowly added dropwise to adjust the pH of the reaction solution to 5. The reaction solution was extracted with 200 mL of ethyl acetate for three times. The combined organic phases were concentrated to give 11 g of beta-carboxy-gamma-butyrolactone.

Reference： [1]Patent: CN106589027,2017,A .Location in patent: Paragraph 0030; 0033; 0034; 0035; 0036; 0037; 0038

60
[ 4344-84-7 ]
3-chloro-5-(hydroxymethyl)tetrahydrofuran-2(3H)-one [ No CAS ]

Reference： [1]Patent: CN106589027,2017,A

61
[ 4344-84-7 ]
[ 10374-60-4 ]

Reference： [1]Patent: CN106589027,2017,A

62
[ 4344-84-7 ]
4-azido-5-(hydroxymethyl)-2,5-dihydrofuran-2(3H)-one [ No CAS ]

Reference： [1]Patent: CN106589027,2017,A

63
[ 4344-84-7 ]
4-azido-5-(methoxymethyl)-2,5-dihydrofuran-2(3H)-one [ No CAS ]

Reference： [1]Patent: CN106589027,2017,A

64
[ 4344-84-7 ]
4-azido-5-(dimethylether)dihydrofuran-2(3H)-acetic acid ester [ No CAS ]

Reference： [1]Patent: CN106589027,2017,A

65
[ 4344-84-7 ]
C₁₁H₁₅N₅O₄ [ No CAS ]

Reference： [1]Patent: CN106589027,2017,A

66
[ 4344-84-7 ]
3'-azido-3'-deoxythymidine [ No CAS ]

Reference： [1]Patent: CN106589027,2017,A

67
[ 4344-84-7 ]
C₂₀H₂₁F₃N₆O₄ [ No CAS ]

Reference： [1]Patent: CN106589027,2017,A

68
[ 4344-84-7 ]
tert-butyl (2-(2-(2-(3-(1-(4-methoxybenzyl)-2,6-dioxopiperidin-3-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethoxy)ethoxy)ethyl)carbamate [ No CAS ]