42558-50-9|(S)-Methyl 3-hydroxypentanoate| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 42558-50-9 ] Purity: 98% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 42558-50-9 ]

CAS No. :	42558-50-9
Formula :	C₆H₁₂O₃
M.W :	132.16
SMILES Code :	CC[C@H](O)CC(OC)=O
MDL No. :	MFCD00216722
InChI Key :	XHFXKKFVUDJSPJ-YFKPBYRVSA-N
Pubchem ID :	10290819

Safety of [ 42558-50-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 42558-50-9 ]

* 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 [ 42558-50-9 ]

[ 42558-50-9 ] Synthesis Path-Downstream 1~35

1
[ 2689-69-2 ]
[ 42558-50-9 ]
[ 42558-50-9 ]

References: [1]Tetrahedron Letters,1982,vol. 23,p. 3479 - 3482.

2
[ 30414-53-0 ]
methyl (3R)-3-hydroxypentanoate [ No CAS ]
[ 42558-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;dichloro[(R)-N-bis(3,5-dimethylphenyl)phosphino-N-methyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine](triphenylphosphine)ruthenium; In methanol; at 20℃; under 16274.9 Torr; for 6h;Conversion of starting material;	Complex 5A-g from Example 9 (2.8 mg; 0.0025 mmol; 0.005 equiv) was placed in a reaction vessel, which was pressurized with argon and vented five times. Argon-degassed methanol (2 mL) was added and the mixture was stirred for 15 minutes. Methyl propionylacetate (63 μL; 0.5 mmol) dissolved in 2 mL of argon-degassed methanol was added and was washed in with 1.0 mL of argon-degassed methanol. The reaction mixture was pressurized with argon and vented five times and then pressurized to 20.7 barg (300 psig) with hydrogen and stirred at ambient temperature for 6 hours. The vessel was vented, then pressurized with argon and vented five times, and the solution was assayed by chiral GC to indicate 100% conversion to methyl (R)-3-hydroxypentanoate with 79.3% ee.

References: [1]Tetrahedron Letters,1986,vol. 27,p. 2657 - 2660.
[2]Tetrahedron Letters,1989,vol. 30,p. 2245 - 2246.
[3]Chemistry Letters,1987,p. 679 - 682.
[4]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 875 - 879.
[5]Chemistry Letters,1987,p. 1267 - 1270.
[6]Chemistry Letters,1987,p. 679 - 682.
[7]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 2473 - 2477.
[8]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 1414 - 1419.
[9]Tetrahedron Letters,1997,vol. 38,p. 6603 - 6606.
[10]Tetrahedron Letters,1990,vol. 31,p. 267 - 270.
[11]Tetrahedron Letters,1989,vol. 30,p. 2245 - 2246.
[12]Chemistry Letters,1987,p. 1267 - 1270.
[13]Tetrahedron Letters,1997,vol. 38,p. 6603 - 6606.
[14]Chemistry Letters,1998,p. 1257 - 1258.
[15]Journal of Organic Chemistry,2000,vol. 65,p. 2586 - 2587.
[16]Journal of the American Chemical Society,2001,vol. 123,p. 1547 - 1555.
[17]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 355 - 363.
[18]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 355 - 363.
[19]Angewandte Chemie - International Edition,2004,vol. 43,p. 5066 - 5069.
[20]Advanced Synthesis and Catalysis,2005,vol. 347,p. 1978 - 1986.
[21]Advanced Synthesis and Catalysis,2006,vol. 348,p. 1157 - 1160.
[22]Tetrahedron Letters,2006,vol. 47,p. 4033 - 4035.
[23]Tetrahedron Letters,1985,vol. 26,p. 4213 - 4216.
[24]Advanced Synthesis and Catalysis,2003,vol. 345,p. 160 - 164.
[25]Patent: US6939981,2005,B1 .Location in patent: Page/Page column 16-17.
[26]Advanced Synthesis and Catalysis,2009,vol. 351,p. 725 - 732.
[27]Advanced Synthesis and Catalysis,2013,vol. 355,p. 209 - 219.
[28]Advanced Synthesis and Catalysis,2013,vol. 355,p. 209 - 219.
[29]European Journal of Inorganic Chemistry,2017,vol. 2017,p. 2762 - 2773.

3
[ 30414-53-0 ]
[ 42558-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;dichloro[(S)-N-diphenylphosphino-N-methyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine](triphenylphosphine)ruthenium; In methanol; at 20℃; under 16274.9 Torr; for 6h;Conversion of starting material;	Complex 5B-a from Example 1 (2.6 mg; 0.0025 mmol; 0.005 equiv) was placed in a reaction vessel, which was pressurized with argon and vented five times. Argon-degassed methanol (2 mL) was added and the mixture was stirred for 15 minutes. Methyl propionylacetate (63 μL; 0.5 mmol) dissolved in 2 mL of argon-degassed methanol was added and was washed in with 1.0 mL of argon-degassed methanol. The reaction mixture was pressurized with argon and vented five times and then pressurized to 20.7 barg (300 psig) with hydrogen and stirred at ambient temperature for 6 hours. The vessel was vented, then pressurized with argon and vented five times, and the solution was assayed by chiral GC to indicate 100% conversion to methyl (S)-3-hydroxypentanoate with 86.2% ee. Chiral GC [30 m×0.25 mm Cyclosil-B (J&W Scientific), 0.25 μm film thickness, 70 C. isothermal]: tR=9.72 min (methyl propionylacetate), tR=10.34 min [methyl (S)-3-hydroxypentanoate], tR=10.80 min [methyl (R)-3-hydroxypentanoate].
	With hydrogen;dichloro(benzene)ruthenium(II) dimer; (11bS,11'bS)-4,4'-(9,9-dimethyl-9H-xanthene-4,5-diyl)-bis-dinaphtha[2,1-d:1',2'-f][1,3,2]dioxaphosphepin; In ethanol; dichloromethane; at 60℃; under 45004.5 Torr; for 20h;Product distribution / selectivity;	[Ru(benzene)Cl2]2 (N) (16 mg, 0.032 mmol) and a diphosphonite (0.067 mmol) were introduced into a 25 ml Schlenk tube. The tube was purged three times with argon before dry dimethylformamide (DMF) (3 ml) was added. The resulting mixture was heated to 100 C. for 30 minutes and then cooled to 60 C. The solvent was removed under reduced pressure, and the catalyst was obtained as a pale green-yellow solid. This catalyst was dissolved in dry dichloromethane (8 ml) and distributed uniformly between 8 vials (in each case 1 ml), which had already been purged three times with argon. A ketone, such as a β-keto ester (III) (0.8 mmol), was introduced into each vessel, then in each case 3 ml of ethanol were added. These were then transferred to a high-pressure autoclave. Once it had been purged three times with H2, the autoclave was adjusted to a pressure 60 bar with H2, and the reactions were stirred magnetically at 60 C. over 20 h. The autoclave was subsequently cooled to room temperature and H2 was cautiously discharged. Samples were taken from each reaction solution and put through a small amount of silica gel before the GC analysis in order to determine the conversions and ee values. The absolute configuration was determined in comparison to known compounds described in the literature.
	With methanesulfonic acid; hydrogen;[RuCl(p-cymene)(VIIa)]Cl; In methanol; at 100℃; under 7500.75 Torr; for 24.3333h;Ultrasonic treatment;Product distribution / selectivity;	A solution of 3.8 ml of methanol and 3 g (23 mmol) of methyl 3-oxopentanoate was treated with [RuCl(p-cymene)(VIIa)]Cl in the manner described in Example 8. This gave 3.03 g of methyl (S)-3-hydroxypentanoate. 99.9% ee (GC); >99% chemical purity.

	With methanesulfonic acid; hydrogen;RuBr2(VIIa); In methanol; at 100℃; under 7500.75 Torr; for 24.3333h;Ultrasonic treatment;Product distribution / selectivity;	A solution of 3.8 ml of methanol and 3 g (23 mmol) of methyl 3-oxopentanoate was treated with 0.0115 mmol of [RuBr2(VIIa)] in the manner described in Example 8. This gave 2.88 g of methyl (S)-3-hydroxypentanoate. 99.5% ee (GC); 95% chemical purity.
	With methanesulfonic acid; hydrogen;[RuCl(benzene)(VIIa)]Cl; In methanol; at 100℃; under 7500.75 Torr; for 24.3333h;Ultrasonic treatment;Product distribution / selectivity;	A solution of 3.8 ml of methanol and 3 g (23 mmol) of methyl 3-oxopentanoate was treated with 0.0115 mmol of [RuCl(benzene)(VIIa)]Cl in the manner described in Example 8. This gave 3.03 g of methyl (S)-3-hydroxy-pentanoate. 99.6 % ee (GC); >99 % chemical purity.
	With dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II); hydrogen; In methanol; at 100℃; under 3800.26 Torr; for 48h;	Synthesis of 1-Azido-3-Pentanol (31) (Scheme 14) A solution of methyl-3-oxo-pentanoate (31) (20 g) noyori hydrogenation with RuCl2 [(S)-BINAP] (60 mg), in methanol was added. The flask was charged with hydrogen gas (5 atm) at 100 C. The resulting suspension was vigorously stirred for 48 hours. The reaction mixture was diluted with methanol and the combined organic layers were filtered through a Celite pad. The combined organic phases were evaporated in a rotary evaporator to yield the product (S) isomer of methyl-3-hydroxy-pentanoate (32). The methyl-3-hydroxy-pentanoate (secondary alcohol-32) was protected with TBDMSCl in the presence of imidazole in dichloro methane. The reaction mixture was stirred for 24 hours at room temperature. This reaction was quenched with aqueous saturated sodium bicarbonate and extracted with dichloro methane. The combined organic phases were dried over Na2SO4 and the combined organic phases were evaporated in a rotary evaporator to yield the TBS protected product (33). A stirred solution of ester was reduced with di-isobutyl aluminum hydride in dichloro methane at -78 C. for 5 hours. This reaction mixture was quenched with saturated aqueous sodium potassium tartarate. The combined organic and aqueous layers were filtered and organic layer was separated by separating funnel. The aqueous layer was extracted with dichloro methane. The combined organic phases were dried over Na2SO4 and the combined organic phases were evaporated in a rotary evaporator to yield the product primary alcohol (34) as a pale yellow liquid. The primary alcohol was protected with methane sulfonyl chloride in the presence of TEA in dichloromethane. The reaction mixture was stirred for 4 hours at 0 C. This reaction was quenched with aqueous saturated sodium bicarbonate and extracted with dichloro methane. The combined organic phases were dried over Na2SO4 and the combined organic phases were evaporated in a rotary evaporator to yield the methane sulfonyl protected product (35). The methane sulfonyl protected primary alcohol was stirred at 70 C. with NaN3 in DMF for 16 hours. A stirred solution of TBS protected secondary alcohol. This reaction was quenched with pre cooled ice water and extracted with diethyl ether. The combined organic phases were dried over Na2SO4. The combined organic phases were evaporated in a rotary evaporator to yield the azido product as a colorless liquid (36). This was deprotected with TBAF in tetrahydrofuran at room temperature. This reaction was quenched with saturated ammonium chloride solution and extracted with diethyl ether; the combined organic phases were dried over Na2SO4 and evaporated on rotary evaporator to yield the product 1-azido-3-pentanol (36A) as a colorless liquid.
> 99.5%Chromat.	With hydrogen; In isopropyl alcohol; at 50℃; under 30003 Torr; for 10h;Autoclave; Glovebox;	General procedure: As a typical run for asymmetric hydrogenation of β-keto esters, 0.026 g Ru/5-BINAPPOPs-1 catalyst, 0.20 g methyl acetoacetate, and 2 mL of isopropanol (ipro) were added to a 30-mL autoclave in a glove box. After the reactor was purged with H2 four times, its pressure was finally adjusted to the desired value, heated from room temperature to the reaction temperature of 50 C, and stirred for 10 h. The catalyst was separated by centrifugation, and the product was analysed using gas chromatography (GC; Agilent 7890B gas chromatograph equipped with a flame ionization detector and a Cyclosil-B capillary column).

References: [1]Tetrahedron Asymmetry,1991,vol. 2,p. 569 - 592.
[2]Tetrahedron Asymmetry,1994,vol. 5,p. 675 - 690.
[3]Journal of Organic Chemistry,2004,vol. 69,p. 7577 - 7581.
[4]Chemical Communications,2019,vol. 56,p. 157 - 160.
[5]European Journal of Organic Chemistry,2014,vol. 2014,p. 323 - 330.
[6]European Journal of Organic Chemistry,2014,vol. 2014,p. 323 - 330.
[7]Synlett,2011,p. 191 - 194.
[8]Journal of the American Chemical Society,1987,vol. 109,p. 5856 - 5858.
[9]Tetrahedron Letters,1995,vol. 36,p. 4801 - 4804.
[10]Journal of the American Chemical Society,1995,vol. 117,p. 4423 - 4424.
[11]Tetrahedron,2001,vol. 57,p. 2563 - 2568.
[12]Journal of the American Chemical Society,2001,vol. 123,p. 1547 - 1555.
[13]Patent: US6359165,2002,B1 .Location in patent: Page column 13.
[14]Patent: US6939981,2005,B1 .Location in patent: Page/Page column 14.
[15]Patent: US2008/255355,2008,A1 .Location in patent: Page/Page column 8-9.
[16]Patent: US2005/250951,2005,A1 .Location in patent: Page/Page column 12.
[17]Patent: US2005/250951,2005,A1 .Location in patent: Page/Page column 13.
[18]Patent: US2005/250951,2005,A1 .Location in patent: Page/Page column 12.
[19]Advanced Synthesis and Catalysis,2013,vol. 355,p. 209 - 219.
[20]Patent: US9250238,2016,B2 .Location in patent: Page/Page column 106; 107; 108.
[21]Cuihua Xuebao/Chinese Journal of Catalysis,2017,vol. 38,p. 890 - 897.

4
[ 42558-50-9 ]
[ 110397-88-1 ]
[ 110397-94-9 ]

References: [1]Tetrahedron,1986,vol. 42,p. 5539 - 5544.

5
[ 42558-50-9 ]
[ 79516-59-9 ]

References: [1]Chemical Communications,2019,vol. 56,p. 157 - 160.
[2]Tetrahedron Asymmetry,1991,vol. 2,p. 569 - 592.

6
[ 84231-00-5 ]
[ 42558-50-9 ]

References: [1]Chemische Berichte,1983,vol. 116,p. 1631 - 1642.

7
[ 42558-50-9 ]
[ 18162-48-6 ]
[ 109346-71-6 ]

Yield	Reaction Conditions	Operation in experiment
	With 1H-imidazole; In dichloromethane; at 20℃; for 24h;	A solution of methyl-3-oxo-pentanoate (31) (20 g) noyori hydrogenation with RuCl2 [(S)-BINAP] (60 mg), in methanol was added. The flask was charged with hydrogen gas (5 atm) at 100 C. The resulting suspension was vigorously stirred for 48 hours. The reaction mixture was diluted with methanol and the combined organic layers were filtered through a Celite pad. The combined organic phases were evaporated in a rotary evaporator to yield the product (S) isomer of methyl-3-hydroxy-pentanoate (32). The methyl-3-hydroxy-pentanoate (secondary alcohol-32) was protected with TBDMSCl in the presence of imidazole in dichloro methane. The reaction mixture was stirred for 24 hours at room temperature. This reaction was quenched with aqueous saturated sodium bicarbonate and extracted with dichloro methane. The combined organic phases were dried over Na2SO4 and the combined organic phases were evaporated in a rotary evaporator to yield the TBS protected product (33). A stirred solution of ester was reduced with di-isobutyl aluminum hydride in dichloro methane at -78 C. for 5 hours. This reaction mixture was quenched with saturated aqueous sodium potassium tartarate. The combined organic and aqueous layers were filtered and organic layer was separated by separating funnel. The aqueous layer was extracted with dichloro methane. The combined organic phases were dried over Na2SO4 and the combined organic phases were evaporated in a rotary evaporator to yield the product primary alcohol (34) as a pale yellow liquid. The primary alcohol was protected with methane sulfonyl chloride in the presence of TEA in dichloromethane. The reaction mixture was stirred for 4 hours at 0 C. This reaction was quenched with aqueous saturated sodium bicarbonate and extracted with dichloro methane. The combined organic phases were dried over Na2SO4 and the combined organic phases were evaporated in a rotary evaporator to yield the methane sulfonyl protected product (35). The methane sulfonyl protected primary alcohol was stirred at 70 C. with NaN3 in DMF for 16 hours. A stirred solution of TBS protected secondary alcohol. This reaction was quenched with pre cooled ice water and extracted with diethyl ether. The combined organic phases were dried over Na2SO4. The combined organic phases were evaporated in a rotary evaporator to yield the azido product as a colorless liquid (36). This was deprotected with TBAF in tetrahydrofuran at room temperature. This reaction was quenched with saturated ammonium chloride solution and extracted with diethyl ether; the combined organic phases were dried over Na2SO4 and evaporated on rotary evaporator to yield the product 1-azido-3-pentanol (36A) as a colorless liquid.

References: [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 323 - 330.
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 323 - 330.
[3]Tetrahedron,1986,vol. 42,p. 5281 - 5290.
[4]Patent: US9250238,2016,B2 .Location in patent: Page/Page column 106; 107; 108.

8
[ 96120-11-5 ]
methyl (3R)-3-hydroxypentanoate [ No CAS ]
[ 42558-50-9 ]

References: [1]Tetrahedron,1985,vol. 41,p. 919 - 926.

9
methyl (3S)-2-<(S)-p-chlorophenylsulfinyl>-3-hydroxypentanoate [ No CAS ]
[ 42558-50-9 ]

References: [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 1273 - 1280.

10
[ 42558-50-9 ]
[ 74-88-4 ]
[ 109715-81-3 ]

References: [1]Liebigs Annalen der Chemie,1989,p. 1263 - 1266.
[2]Tetrahedron,1990,vol. 46,p. 5563 - 5566.

11
[ 67-56-1 ]
[ 30608-62-9 ]
[ 201230-82-2 ]
[ 42558-50-9 ]

References: [1]Journal of Organic Chemistry,1999,vol. 64,p. 2164 - 2165.

12
[ 109462-42-2 ]
Me₂CuLi [ No CAS ]
[ 42558-50-9 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 2513 - 2516.
[2]Helvetica Chimica Acta,1987,vol. 70,p. 142 - 152.

13
[ 908094-01-9 ]
butyl 3-oxopentanoate [ No CAS ]
methyl (3R)-3-hydroxypentanoate [ No CAS ]
[ 42558-50-9 ]

References: [1]Tetrahedron,1999,vol. 55,p. 7519 - 7528.

14
[ 540-88-5 ]
[ 42558-50-9 ]
[ 350612-29-2 ]

References: [1]Synthesis,2001,p. 937 - 942.

15
[ 42558-50-9 ]
[ 790699-26-2 ]