93061-20-2|(2R,3R)-3-(Ethoxycarbonyl)oxirane-2-carboxylic acid| Ambeed

CAS No. :	93061-20-2
Formula :	C₆H₈O₅
M.W :	160.12
SMILES Code :	O=C([C@@H]1O[C@H]1C(O)=O)OCC
MDL No. :	MFCD18829017
InChI Key :	MWMZDXCRDIBPCO-QWWZWVQMSA-N
Pubchem ID :	13150798

Safety of [ 93061-20-2 ]

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 [ 93061-20-2 ]

* 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 [ 93061-20-2 ]

[ 93061-20-2 ] Synthesis Path-Downstream 1~54

1
[ 6066-82-6 ]
[ 93061-20-2 ]
[ 159517-12-1 ]

References: [1]Tetrahedron,1994,vol. 50,p. 8381 - 8392.

2
[ 100-02-7 ]
[ 93061-20-2 ]
[ 100569-81-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1987,vol. 35,p. 1098 - 1104.

3
[ 771-61-9 ]
[ 93061-20-2 ]
[ 1027190-58-4 ]

References: [1]Tetrahedron,1994,vol. 50,p. 8381 - 8392.

4
[ 74243-85-9 ]
[ 93061-20-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With ethanol; potassium hydroxide; at 0 - 20℃; for 19.0333h;	To an ice cooled solution of (2R ,3R)-diethyl 2,3 -epoxy succinate (250 mg, 1.33 mmol, Sigma-Aldrich Corporation) in ethanol (3 mL) was added dropwise a solution of potassium hydroxide (89 mg, 1.594 mmol, VWR International, LLC) in ethanol (2.0 mL) over 2 minutes. After this addition the reaction mixture was allowed to stir at 0 C for 3 h. The resulting reaction mixture became a gel-like mixture. The cooling bath was then removed and the reaction mixture was stirred for further 16 h at room temperature. Afterwards the ethanol was removed in vacuo leaving an off white solid. This salt was then taken up with 10 mL of water and washed three times with dichloride methane. The aqueous phase was acidified by addition of 2 M HC1 to pH 3 and extracted with ethyl acetate (10 mL x 3). The combined organic phase was dried over MgSCri, filtered, and concentrated in vacuo. After drying the pure product (2R,3R)-3- (ethoxycarbonyl)oxirane-2-carboxylic acid (170 mg, 1.06 mmol, 80 % yield) was obtained as a colorless oil. 1H NMR (400 MHz, CDC13) d 8.41-9.03 (brs, 1H), 4.29 (ttd, J= 3.6, 7.1, 10.7 Hz, 2H), 3.72-3.73 (m, 1H), 3.70-3.72 (m, 1H), 1.33 (t, J=1.2 Hz, 3H). [Ref: ACS Chemical Biology, 5(3), 279-285; 2010]

References: [1]Patent: WO2021/81212,2021,A1 .Location in patent: Paragraph 0317-0318.
[2]Helvetica Chimica Acta,2003,vol. 86,p. 222 - 232.
[3]Chemical and Pharmaceutical Bulletin,1987,vol. 35,p. 1098 - 1104.
[4]Tetrahedron,1994,vol. 50,p. 8381 - 8392.
[5]Journal of Medicinal Chemistry,2010,vol. 53,p. 2038 - 2050.
[6]Journal of Medicinal Chemistry,2013,vol. 56,p. 6054 - 6068.

5
[ 93061-20-2 ]
[ 110755-29-8 ]
D-trans-epoxysuccinyl-L-phenylalanylamido(3-methyl)butane ethylester [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1993,vol. 28,p. 917 - 926.

6
[ 93061-20-2 ]
[ 154415-69-7 ]
[ 154461-40-2 ]

References: [1]European Journal of Medicinal Chemistry,1993,vol. 28,p. 917 - 926.

7
[ 93061-20-2 ]
[ 154415-70-0 ]
[ 154461-41-3 ]

References: [1]European Journal of Medicinal Chemistry,1993,vol. 28,p. 917 - 926.

8
[ 93061-20-2 ]
[ 154415-74-4 ]
[ 154461-42-4 ]

References: [1]European Journal of Medicinal Chemistry,1993,vol. 28,p. 917 - 926.

9
ethyl (2R,3R)-trans-2,3-epoxysuccinate potassium salt [ No CAS ]
[ 93061-20-2 ]

References: [1]Tetrahedron,1994,vol. 50,p. 8381 - 8392.

10
[ 74509-15-2 ]
[ 93061-20-2 ]
[ 199452-12-5 ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 1789 - 1797.

11
[ 93061-20-2 ]
[ 117560-24-4 ]
(2S,3S)-3-[[[(1R)-3-phenyl-1-[(phenylmethoxy)carbonyl]propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

12
[ 93061-20-2 ]
[ 117560-24-4 ]
(2S,3S)-3-[[[(1S)-3-phenyl-1-[(phenylmethoxy)carbonyl]propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

13
[ 93061-20-2 ]
[ 325789-60-4 ]
(2S,3S)-3-[[[(1R)-1-[[(3-methylbutyl)amino]carbonyl]-3-(4-hydroxyphenyl)propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

14
[ 93061-20-2 ]
[ 500228-04-6 ]
[ 500228-07-9 ]

References: [1]Helvetica Chimica Acta,2003,vol. 86,p. 222 - 232.

15
[ 5241-58-7 ]
[ 93061-20-2 ]
(2R,3R)-3-((S)-1-Carbamoyl-2-phenyl-ethylcarbamoyl)-oxirane-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1553 - 1574.

16
[ 10466-61-2 ]
[ 93061-20-2 ]
(2R,3R)-3-((S)-1-Carbamoyl-3-methyl-butylcarbamoyl)-oxirane-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1553 - 1574.

17
[ 64-04-0 ]
[ 93061-20-2 ]
(2R,3R)-3-Phenethylcarbamoyl-oxirane-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1553 - 1574.

18
[ 93061-20-2 ]
L-alanine-benzylamide hydrochloride [ No CAS ]
(2R,3R)-3-((S)-1-Benzylcarbamoyl-ethylcarbamoyl)-oxirane-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1553 - 1574.

19
[ 93061-20-2 ]
[ 646532-77-6 ]
[ 646532-01-6 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1553 - 1574.

20
[ 93061-20-2 ]
[ 646532-80-1 ]
3-{N'-[2-(2-benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyrylamino)-3-methyl-butyryl]-N-tert-butoxycarbonylmethyl-hydrazinocarbonyl}-oxirane-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1553 - 1574.

21
[ 93061-20-2 ]
[ 646532-81-2 ]
[ 646531-04-6 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1553 - 1574.
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 4958 - 4960.

22
[ 93061-20-2 ]
[ 646532-82-3 ]
[ 646532-36-7 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1553 - 1574.

23
[ 93061-20-2 ]
[ 646532-79-8 ]
[ 646531-07-9 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1553 - 1574.
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 4958 - 4960.

24
[ 93061-20-2 ]
[ 100-46-9 ]
(2R,3R)-3-Benzylcarbamoyl-oxirane-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1553 - 1574.

25
[ 93061-20-2 ]
[ 7568-93-6 ]
(2R,3R)-3-(2-Hydroxy-2-phenyl-ethylcarbamoyl)-oxirane-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1553 - 1574.

26
[ 646532-83-4 ]
[ 93061-20-2 ]
(2R,3R)-3-(N²-(N-benzyloxycarbonylleucylleucyl)-N¹-isobutylhydrazinocarbonyl)oxirane-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4958 - 4960.

27
[ 93061-20-2 ]
[ 646532-76-5 ]
(2R,3R)-3-(N²-(N-benzyloxycarbonylalanylalanyl)-N¹-carbamoylmethylhydrazinocarbonyl)oxirane-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4958 - 4960.

28
[ 93061-20-2 ]
(2S,3S)-3-[[[(1S)-3-phenyl-1-(carboxyl)propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

29
[ 93061-20-2 ]
(2S,3S)-3-[[[(1R)-3-phenyl-1-(carboxyl)propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

30
[ 93061-20-2 ]
(2S,3S)-3-[[[(1R)-3-phenyl-1-[[phenylamino]carbonyl]propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

31
[ 93061-20-2 ]
(2S,3S)-3-[[[(1R)-3-phenyl-1-[[(phenylmethyl)amino]carbonyl]propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

32
[ 93061-20-2 ]
(2S,3S)-3-[[[(1R)-3-phenyl-1-[[(4-hydroxybutyl)amino]carbonyl]propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

33
[ 93061-20-2 ]
(2S,3S)-3-[[[(1S)-3-phenyl-1-[[(4-hydroxybutyl)amino]carbonyl]propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

34
[ 93061-20-2 ]
(2S,3S)-3-[[[(1R)-3-phenyl-1-[[(5-hydroxypentyl)amino]carbonyl]propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

35
[ 93061-20-2 ]
(2S,3S)-3-[[[(1R)-3-phenyl-1-[[(cyclohexylmethyl)amino]carbonyl]propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

36
[ 93061-20-2 ]
(2S,3S)-3-[[[(1R)-3-phenyl-1-[[(4-t-butyldimethylsilanyloxybutyl)amino]carbonyl]propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

37
[ 93061-20-2 ]
(2S,3S)-3-[[[(1S)-3-phenyl-1-[[(4-t-butyldimethylsilanyloxybutyl)amino]carbonyl]propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

38
[ 93061-20-2 ]
(2S,3S)-3-[[[(1R)-3-phenyl-1-[[(5-t-butyldimethylsilanyloxypentyl)amino]carbonyl]propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9747 - 9762.

39
[ 93061-20-2 ]
[ 159517-32-5 ]

References: [1]Tetrahedron,1994,vol. 50,p. 8381 - 8392.

40
[ 93061-20-2 ]
[ 159517-33-6 ]

References: [1]Tetrahedron,1994,vol. 50,p. 8381 - 8392.

41
[ 93061-20-2 ]
[ 159415-39-1 ]

References: [1]Tetrahedron,1994,vol. 50,p. 8381 - 8392.

42
[ 93061-20-2 ]
N-<<(2R,3R)-3-trans-(ethoxycarbonyl)oxiran-2-yl>carbonyl>-leucyl-agmatine*1/2H2SO4 [ No CAS ]

References: [1]Tetrahedron,1994,vol. 50,p. 8381 - 8392.

43
[ 93061-20-2 ]
[ 111612-35-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,1987,vol. 35,p. 1098 - 1104.

44
[ 93061-20-2 ]
[ 111612-34-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1987,vol. 35,p. 1098 - 1104.

Yield	Reaction Conditions	Operation in experiment
4.76 g (42.7%)		Reference Example 5 In 50 ml of ethanol is dissolved 13.1 g (69.7 mmole), of diethyl (2R,3R)-epoxysuccinate, and a solution of 3.94 g of potassium hydroxide in 120 ml of ethanol is added dropwise to the solution under ice-cooling with stirring. After the stirring under ice-cooling for 3 hours, the ethanol is distilled off under reduced pressure. 50 ml of water and 100 ml of ether are added to the residue to a solution, and the aqueous layer is separated. The ether layer is extracted three times with dilute aqueous sodium chloride solution, and the aqueous layers are combined and acidified with 3N hydrochloric acid. The solution, after being saturated with sodium chloride, is extracted four times with ethyl acetate, and the extract is washed with aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure, and the residue is distilled under reduced pressure to give 4.76 g (42.7%) of (2R,3R)-epoxysuccinic acid monoethyl ester as a colorless oil having a boiling point of 121-122 C. (0.85 mmHg). The product, upon standing, crystallizes, and the crystals are recrystallized from isopropyl ether-petroleum ether (1:2) to give colorless crystals. Melting point, 55-56 C. IR (KBr) cm-1: 3,420(br.), 1,740(br.), 1,380, 1,310, 1,210. NMR CDCl3)δ: 1.33(3H,t,J=7 Hz,CH3), 3.72(2H,s,2xCH), 4.28 (2H,q,J=7 Hz,CH2), 10.63(1H,s,COOH).

46
[ 93061-20-2 ]
N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-5-Acetylamino-6-amino-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide [ No CAS ]
C₅₀H₅₇N₃O₁₄ [ No CAS ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 605 - 616.

47
[ 93061-20-2 ]
[ 91-59-8 ]
[ 169205-78-1 ]
[ 1207983-16-1 ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2038 - 2050.

48
[ 93061-20-2 ]
[ 169205-78-1 ]
[ 1207983-05-8 ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2038 - 2050.

49
[ 1308595-36-9 ]
[ 93061-20-2 ]
[ 1448429-32-0 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6054 - 6068.

50
C₁₅H₁₈FN₃OS [ No CAS ]
[ 93061-20-2 ]
[ 1448429-34-2 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6054 - 6068.

51
C₁₅H₁₄FN₅OS [ No CAS ]
[ 93061-20-2 ]
[ 1448429-41-1 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6054 - 6068.

52
C₁₃H₁₂FN₅OS [ No CAS ]
[ 93061-20-2 ]
[ 1448429-43-3 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6054 - 6068.

53
[ 87-91-2 ]
[ 93061-20-2 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6054 - 6068.

54
[ 80640-14-8 ]
[ 93061-20-2 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6054 - 6068.

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Epoxidation • Ester Cleavage • Reactions of Epoxides • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

Related Parent Nucleus of
[ 93061-20-2 ]

Epoxides

A865265 [89886-73-7]

(2S,3S)-3-(Ethoxycarbonyl)oxirane-2-carboxylic acid

Similarity: 1.00

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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

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CAS No.: 93061-20-2

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