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Chemical Structure| 88496-70-2 Chemical Structure| 88496-70-2
Chemical Structure| 88496-70-2

*Storage: Inert atmosphere,Room Temperature.

(R)-Methyl 4-chloro-3-hydroxybutanoate

CAS No.: 88496-70-2

4.5 *For Research Use Only !

Cat. No.: A175863 Purity: 95%

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Product Details of [ 88496-70-2 ]

CAS No. :88496-70-2
Formula : C5H9ClO3
M.W : 152.58
SMILES Code : O=C(OC)C[C@@H](O)CCl
MDL No. :MFCD00273367
InChI Key :WMRINGSAVOPXTE-SCSAIBSYSA-N
Pubchem ID :10920707

Safety of [ 88496-70-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H318-H412
Precautionary Statements:P264-P270-P273-P280-P301+P312+P330-P305+P351+P338+P310-P501
Class:9
UN#:3082
Packing Group:

Application In Synthesis [ 88496-70-2 ]

* 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.

  • Upstream synthesis route of [ 88496-70-2 ]

[ 88496-70-2 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 32807-28-6 ]
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  • [ 86728-93-0 ]
References: [1] Tetrahedron Letters, 1986, vol. 27, # 23, p. 2657 - 2660.
[2] Angewandte Chemie, 1984, vol. 96, # 2, p. 155 - 156.
[3] Journal of the Chemical Society, Chemical Communications, 1988, # 4, p. 264 - 266.
[4] Journal of the American Chemical Society, 1995, vol. 117, # 15, p. 4423 - 4424.
[5] Journal of the Chemical Society, Chemical Communications, 1988, # 4, p. 264 - 266.
[6] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 3, p. 875 - 879.
[7] Tetrahedron Letters, 1985, vol. 26, # 35, p. 4213 - 4216.
[8] Tetrahedron Asymmetry, 2009, vol. 20, # 9, p. 1057 - 1061.
[9] Journal of Molecular Catalysis B: Enzymatic, 2010, vol. 65, # 1-4, p. 37 - 40.
[10] Biocatalysis and Biotransformation, 2011, vol. 29, # 6, p. 328 - 336.
  • 2
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YieldReaction ConditionsOperation in experiment
10.4 g With D-glucose In aq. phosphate buffer at 20℃; Green chemistry; Enzymatic reaction 12.5 g of methyl 4-chloroacetoacetate and 125 mL of 0.1 M PBS buffer, 15.0 g of glucose were added.ThepH was adjusted to 6.7by stirring at room temperature,and 0.15 g of the main enzyme, 0.01 g of the coenzyme and 0.5 g of the dehydrogenase were added to the reaction system in one portion, and the reaction was completed.0.8 g of diatomaceous earth and 150 ml of toluene were added, stirred, and filtered.After the filtrate was washed with a 10percent by weight aqueous solution of sodium chloride, the organic layer was concentratedto give 10.4 g of a brownish yellow liquid, that is, methyl (R)-(+)-4-chloro-3-hydroxybutanoate.The active enzyme was not detected by the WOOD method.
References: [1] Tetrahedron Asymmetry, 2010, vol. 21, # 5, p. 566 - 570.
[2] Chemosphere, 1999, vol. 38, # 10, p. 2243 - 2246.
[3] Organic Letters, 2006, vol. 8, # 19, p. 4227 - 4229.
[4] Patent: CN109053479, 2018, A, . Location in patent: Paragraph 0074; 0075.
  • 3
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YieldReaction ConditionsOperation in experiment
26% With N-chloro-succinimide; triphenylphosphine In dichloromethane at 5 - 20℃; for 18.3333 h; [00201] (R)-Methyl 4-chloro-3-hydroxybutanoate OH Q-o'To a solution of (R)-methyl 3,4-dihydroxybutanoate (125.1 g, 0.93 mol) in CH2Cl2 (1.8 L) was added PPh3 (244.5 g, 0.93 mol) and slowly added NCS (124.2g, 0.93 mol) under ice water cooling. The mixture was stirred at 5 0C for 20 min and then stirred for 18 h at room temperature. After evaporating the solvent, the residue was purified by column chromatography (P.E\\E.A 20:1-5:1, gradient) to give (R)-methyl 4-chloro-3-hydroxybutanoate (33 g, 26percent over 3 steps). 1H NMR (300MHz, CDCl3) ? 4.18-4.25 (m, 1 H), 3.68 (s, 3 H), 3.55-3.60 (m, 2 H), 3.32- 3.33 (d, J= 4.2 Hz, 1 H), 2.52-2.68 (m, 2 H).
References: [1] Patent: WO2007/21982, 2007, A2, . Location in patent: Page/Page column 67-68.
  • 4
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  • [ 143-33-9 ]
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References: [1] Organic Letters, 2006, vol. 8, # 19, p. 4227 - 4229.
  • 5
  • [ 4128-31-8 ]
  • [ 32807-28-6 ]
  • [ 5978-70-1 ]
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References: [1] Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1730 - 1732.
  • 6
  • [ 773837-37-9 ]
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References: [1] European Journal of Organic Chemistry, 2009, # 14, p. 2293 - 2298.
  • 7
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  • [ 58081-05-3 ]
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  • [ 5469-16-9 ]
References: [1] Advanced Synthesis and Catalysis, 2003, vol. 345, # 4, p. 437 - 455.
  • 8
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  • [ 109462-42-2 ]
References: [1] Tetrahedron Asymmetry, 2009, vol. 20, # 4, p. 483 - 488.
  • 9
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References: [1] Organic Letters, 2006, vol. 8, # 19, p. 4227 - 4229.
  • 10
  • [ 32807-28-6 ]
  • [ 67-63-0 ]
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  • [ 67-64-1 ]
References: [1] Chemistry - A European Journal, 2010, vol. 16, # 36, p. 11012 - 11019.
  • 11
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References: [1] Tetrahedron Letters, 1986, vol. 27, # 43, p. 5275 - 5276.
  • 12
  • [ 10488-68-3 ]
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References: [1] Tetrahedron Asymmetry, 1996, vol. 7, # 11, p. 3109 - 3112.
[2] Tetrahedron Asymmetry, 1996, vol. 7, # 11, p. 3109 - 3112.
 

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