[ CAS No. 121-39-1 ] {[proInfo.proName]}

Name: 121-39-1|Ethyl 3-phenylglycidate|90%
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SKU: A406238
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3d Animation Molecule Structure of 121-39-1

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Quality Control of [ 121-39-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 121-39-1 ]

SDS Specification

Alternatived Products of [ 121-39-1 ]

Product Details of [ 121-39-1 ]

CAS No. :	121-39-1	MDL No. :	MFCD00005123
Formula :	C₁₁H₁₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GOMAKLPNAAZVCJ-UHFFFAOYSA-N
M.W :	192.21	Pubchem ID :	8469
Synonyms :

Calculated chemistry of [ 121-39-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.89
TPSA :	38.83 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.05
Log Po/w (XLOGP3) :	1.7
Log Po/w (WLOGP) :	1.37
Log Po/w (MLOGP) :	1.3
Log Po/w (SILICOS-IT) :	2.33
Consensus Log Po/w :	1.75

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.16
Solubility :	1.34 mg/ml ; 0.00698 mol/l
Class :	Soluble
Log S (Ali) :	-2.13
Solubility :	1.42 mg/ml ; 0.0074 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.71
Solubility :	0.373 mg/ml ; 0.00194 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.71

Safety of [ 121-39-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 121-39-1 ]

* 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 [ 121-39-1 ]

[ 121-39-1 ] Synthesis Path-Downstream 1~108

1
[ 121-39-1 ]
[ 141-97-9 ]
4-acetyl-5-oxo-2-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Zhurnal Obshchei Khimii,1937,vol. 7,p. 2373
Chemisches Zentralblatt,1938,vol. 109,p. 845

2
[ 121-39-1 ]
[ 124-40-3 ]
[ 717107-08-9 ]

Reference： [1]Bulletin de la Societe Chimique de France,1907,vol. <4> 1,p. 553,556

3
[ 121-39-1 ]
[ 137-07-5 ]
2-(α-hydroxy-benzyl)-4<i>H</i>-benzo[1,4]thiazin-3-one [ No CAS ]

Reference： [1]Journal of the Chemical Society,1949,p. 278,281

4
[ 121-39-1 ]
[ 137-07-5 ]
[ 27068-83-3 ]

Reference： [1]Chemical and pharmaceutical bulletin,1970,vol. 18,p. 2028 - 2037

5
[ 121-39-1 ]
[ 603-35-0 ]
[ 4192-77-2 ]

Reference： [1]Chemische Berichte,1955,vol. 88,p. 1654,1663

6
[ 121-39-1 ]
[ 105-53-3 ]
[ 20375-19-3 ]

Reference： [1]Zhurnal Obshchei Khimii,1937,vol. 7,p. 2373
Chemisches Zentralblatt,1938,vol. 109,p. 845

7
[ 121-39-1 ]
[ 4850-49-1 ]

Reference： [1]Helvetica Chimica Acta,1932,vol. 15,p. 1250,1265

8
[ 121-39-1 ]
[ 828-01-3 ]

Reference： [1]Chemische Berichte,1956,vol. 89,p. 671,675

9
[ 64-17-5 ]
[ 6286-30-2 ]
[ 121-39-1 ]
[ 588-73-8 ]
[ 588-72-7 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 2639,2640

10
[ 100-52-7 ]
[ 105-39-5 ]
[ 121-39-1 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2004,vol. 43,p. 957 - 963
[2]Synthetic Communications,1982,vol. 12,p. 355 - 360
[3]Tetrahedron,1990,vol. 46,p. 2611 - 2622
[4]Tetrahedron Letters,2007,vol. 48,p. 4489 - 4493
[5]Justus Liebigs Annalen der Chemie,1892,vol. 271,p. 161
[6]Canadian Journal of Chemistry,1982,vol. 60,p. 2707 - 2710
[7]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2178 - 2184
[8]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2010,vol. 49,p. 978 - 984

11
[ 121-39-1 ]
[ 113-00-8 ]
[ 90840-42-9 ]

Reference： [1]Journal of the Chemical Society,1963,p. 2747 - 2756

12
[ 121-39-1 ]
[ 113-00-8 ]
[ 96418-64-3 ]

Reference： [1]Journal of the Chemical Society,1963,p. 2747 - 2756

13
[ 121-39-1 ]
[ 62-53-3 ]
[ 18366-43-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With iron oxide; In neat (no solvent); at 20℃; for 20h;Green chemistry;	General procedure: Epoxide (1.5-2 mmol), amine(1.0 mmol) and nano Fe3O4 (10 mol%, 23 mg, particle size= <50 nm) were stirred at r.t. open to the atmosphere for20 h. EtOAc (1-2 mL) was then added and the mixture wasstirred for 1-2 min. A magnet was then externally applied tothe flask and the catalyst was allowed to accumulate at thewalls of the flask; the resulting clear solution was transferredto a fresh flask by using a pipette. This step was repeatedtwice more, and the combined organic layers were dried overanhydrous Na2SO4, filtered, and the solvent evaporated.Purification by column chromatography on silica gel(EtOAc-hexanes, 20:80) gave the pure products. (c) All thereactions were carried out at r.t (range 28-32 C) unlessotherwise mentioned. (d) When one of the substrates(epoxide or amine) was a solid, to facilitate homogeneousstirring, the reaction was carried out by using 1 mmol of thesolid sample and the other corresponding liquid sample inexcess (2 mmol) and the yield was calculated based on thelimiting reagent.

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 8768 - 8780
[2]Journal of Organic Chemistry,2007,vol. 72,p. 3713 - 3722
[3]Synlett,2014,vol. 25,p. 835 - 842
[4]Journal of Organic Chemistry,1969,vol. 34,p. 175 - 179

14
[ 103-36-6 ]
[ 121-39-1 ]

Reference： [1]Organic Syntheses,1997,vol. 74,p. 91 - 91
[2]European Journal of Inorganic Chemistry,2014,vol. 2014,p. 5777 - 5782
[3]Angewandte Chemie,1986,vol. 98,p. 565
[4]Advanced Synthesis and Catalysis,2017,vol. 359,p. 476 - 484
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2006,vol. 45,p. 943 - 950
[6]Molecular Crystals and Liquid Crystals,2010,vol. 522,p. 105 - 111
[7]Organic Letters,2008,vol. 10,p. 2095 - 2098
[8]Green Chemistry,2009,vol. 11,p. 1589 - 1594
[9]Chemical Communications,2012,vol. 48,p. 6541 - 6543
[10]Inorganic Chemistry,2013,vol. 52,p. 3620 - 3626
[11]Journal of Materials Chemistry A,2013,vol. 1,p. 9037 - 9045

15
[ 121-39-1 ]
[ 2627-86-3 ]
[ 79898-20-7 ]
(S)-1-phenylethylammonium (2S,3R)-2,3-epoxy-3-phenylpropionate [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1984,vol. 57,p. 1920 - 1928

16
[ 121-39-1 ]
[ 3886-69-9 ]
[ 79898-18-3 ]
(R)-1-phenylethylammonium (2R,3S)-2,3-epoxy-3-phenylpropionate [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1984,vol. 57,p. 1920 - 1928

17
[ 121-39-1 ]
[ 10541-78-3 ]
[ 93886-49-8 ]

Reference： [1]European Journal of Medicinal Chemistry,1984,vol. 19,p. 235 - 242

18
[ 121-39-1 ]
[ 18039-42-4 ]
[ 93742-50-8 ]
[ 93742-49-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 1933 - 1941

19
[ 121-39-1 ]
[ 103-36-6 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 22 - 25
[2]Tetrahedron Letters,2010,vol. 51,p. 5466 - 5468
[3]Journal of Organic Chemistry,2009,vol. 74,p. 3913 - 3918
[4]Molecular catalysis,2017,vol. 443,p. 175 - 178
[5]Synthetic Communications,1989,vol. 19,p. 491 - 500

20
[ 121-39-1 ]
[ 25957-39-5 ]
[ 129939-42-0 ]
[ 129939-41-9 ]

Reference： [1]Tetrahedron,1990,vol. 46,p. 2611 - 2622

21
[ 121-39-1 ]
[ 60727-93-7 ]

Reference： [1]Journal of Fluorine Chemistry,1995,vol. 70,p. 1 - 4
[2]Canadian Journal of Chemistry,1982,vol. 60,p. 2707 - 2710

22
[ 121-39-1 ]
3-Fluoro-2-hydroxy-3-phenyl-propionic acid ethyl ester [ No CAS ]
3-Fluoro-2-hydroxy-3-phenyl-propionic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,1981,vol. 17,p. 565 - 580

23
[ 88624-60-6 ]
[ 121-39-1 ]

Reference： [1]Chemistry Letters,1981,p. 1129 - 1132

24
[ 25709-55-1 ]
[ 100-52-7 ]
[ 121-39-1 ]

Reference： [1]Synthetic Communications,1987,vol. 17,p. 1593 - 1602
[2]Journal of Organic Chemistry,1990,vol. 55,p. 501 - 504

25
[ 100-52-7 ]
[ 105-36-2 ]
[ 121-39-1 ]

Reference： [1]Journal of Fluorine Chemistry,1981,vol. 17,p. 565 - 580

26
[ 74087-85-7 ]
[ 4192-77-2 ]
[ 121-39-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1990,p. 349 - 352

27
[ 4192-77-2 ]
[ 121-39-1 ]

Yield	Reaction Conditions	Operation in experiment
85%Chromat.	With acetonitrile complex of hypofluorous acid; at 60℃;Product distribution / selectivity;	This reaction is effected in seconds whereas the prior art specifies long reaction times and 3 equivalents of HOF to achieve an 85% yield. In the case of this substrate, the reaction products were identified by their 1H NMR and 13C{1H} NMR spectra, and were not isolated.

Reference： [1]Journal of Organic Chemistry,1985,vol. 50,p. 2847 - 2853
[2]Tetrahedron,1997,vol. 53,p. 7649 - 7670
[3]Tetrahedron Letters,1996,vol. 37,p. 3769 - 3772
[4]Journal of the Indian Chemical Society,1983,vol. 60,p. 300 - 302
[5]Chemistry Letters,2007,vol. 36,p. 848 - 849
[6]Patent: US2011/40092,2011,A1 .Location in patent: Page/Page column 7

28
[ 62355-67-3 ]
[ 121-39-1 ]

Reference： [1]Journal of Organometallic Chemistry,1987,vol. 336,p. C33 - C36

29
[ 121-39-1 ]
[ 4192-77-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With bis(acetylacetonate)nickel(II); diethylzinc; In tetrahydrofuran; hexane; at 50℃;Inert atmosphere;Catalytic behavior;	Ethyl cinnamate (2a)2: To a solution of Ni(acac)2 (25.7 mg, 0.1 mmol) in dry THF (3 mL) were successively added <strong>[121-39-1]ethyl 3-phenylglycidate</strong> (192 mg, 1 mmol) and diethylzinc (2.4 mmol, 1.0 M hexane solution) via syringe under argon atmosphere. The mixture was stirred at ambient temperature for 48 h. The mixture was diluted with 30 mL of CH2Cl2 and washed with sat. NH4Cl aq. and then brine. The organic layer was dried over MgSO4 and concentrated in vacuo and the residual oil was subjected to column chromatography over silica gel (hexane/EtOAc = 4/1 v/v) to give 2a (164 mg, 93%, Rf = 0.3; hexane/ethyl acetate = 20/1 v/v). E-isomer; 1H NMR (400 MHz,CDCl3) delta 1.32 (t, J = 7.4 Hz, 3H), 4.25 (q, J = 7.4 Hz, 2H), 6.43 (d, J = 16.0 Hz, 1H), 7.34-7.37 (m,3H), 7.49-7.52 (m, 2H), 7.68 (d, J = 16.0 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 14.2, 60.3, 118.1,127.9, 128.1, 128.7, 130.1, 134.3, 144.4, 166.8; MS (EI) m/z (relative intensity): 176 (M+, 25), 148(13), 131 (100), 103 (32), 77 (30), 51 (20).
79%	With [ReOCl3(PPh3)2]; In toluene; for 1h;Reflux;	In a typical experiment, to a solution of oxo-rhenium complex (10.0 mol %) in toluene (3 mL) was added the epoxide (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the refPreviewPlaceHolderTable 1, refPreviewPlaceHolderTable 2 and refPreviewPlaceHolderTable 3) and the progress of the reaction was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford the alkenes.

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 4118 - 4123
[2]Tetrahedron Letters,2020,vol. 61
[3]Tetrahedron Letters,2003,vol. 44,p. 2355 - 2357
[4]Tetrahedron Letters,2011,vol. 52,p. 6960 - 6962
[5]Journal of the American Chemical Society,1995,vol. 117,p. 4468 - 4475

30
[ 121-39-1 ]
[ 1004-00-8 ]
[ 30302-01-3 ]

Reference： [1]Chemical and pharmaceutical bulletin,1970,vol. 18,p. 2028 - 2037

31
[ 617-33-4 ]
[ 100-52-7 ]
[ 121-39-1 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 2803 - 2816

32
[ 5348-42-5 ]
[ 121-39-1 ]
(3R,4R)-7,8-Dichloro-3-hydroxy-4-phenyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one [ No CAS ]
(3S,4R)-7,8-Dichloro-3-hydroxy-4-phenyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one [ No CAS ]

Reference： [1]Bulletin des Societes Chimiques Belges,1996,vol. 105,p. 785 - 786

33
[ 121-39-1 ]
[ 3171-45-7 ]
(3R,4R)-3-Hydroxy-7,8-dimethyl-4-phenyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one [ No CAS ]
(3S,4R)-3-Hydroxy-7,8-dimethyl-4-phenyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one [ No CAS ]

Reference： [1]Bulletin des Societes Chimiques Belges,1996,vol. 105,p. 785 - 786

34
[ 121-39-1 ]
[ 95-54-5 ]
(3R,4R)-3-Hydroxy-4-phenyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one [ No CAS ]
(3S,4R)-3-Hydroxy-4-phenyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one [ No CAS ]

Reference： [1]Bulletin des Societes Chimiques Belges,1996,vol. 105,p. 785 - 786

35
[ 121-39-1 ]
[ 84024-60-2 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 14772 - 14773
[2]Angewandte Chemie - International Edition,2008,vol. 47,p. 4188 - 4191
[3]Tetrahedron,1997,vol. 53,p. 8887 - 8912

36
[ 121-39-1 ]
[ 15399-27-6 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 3417 - 3419
[2]Organic Letters,2003,vol. 5,p. 4665 - 4668
[3]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2178 - 2184
[4]ACH - Models in Chemistry,1998,vol. 135,p. 625 - 640
[5]Chemical and pharmaceutical bulletin,1970,vol. 18,p. 2028 - 2037

37
[ 121-39-1 ]
[ 2021-28-5 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1997,vol. 70,p. 1101 - 1107

Yield	Reaction Conditions	Operation in experiment
53%		EXAMPLE 43 Ethyl 2,3-epoxy-3-phenyl propionate Using the method of Example 36 with ethyl glyoxylate but using 1 mmol of dimethyl sulfide gave the title compound in 53% yield as a clear oil. deltaH (CDCl3, 250 MHz): 7.4-7.2(5H,m), 4.36-4.20 (2H,m), 4.10 (1H,d,J=2.0 Hz), 3.51 (1H,d,J=2.0 Hz), 1.50(3H,t,J=8 Hz)ppm.
		In the same manner as in Example 1, ethyl 3-phenylpyruvate was obtained from ethyl 3-phenylglycidate. The results are shown in the following tables.
		Examples of suitable phenylglycidates include: n-butyl 3-methyl-3-phenylglycidate (93963-69-0); ethyl 3-(4-methoxyphenyl)glycidate (16546-01-3); ethyl 3-(4-methylphenyl)glycidate (52788-71-3); ethyl 3-phenylglycidate (121-39-1); ethyl 3-methyl-3-phenylglycidate (77-83-8) methyl 3-methyl-3-phenylglycidate (99334-18-6).

	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃;	General procedure: To a solution of Compound 84A (10 mmol) in dichloromethane (50 mL) was added m-CPBA (1.72 g, 10 mmol). The mixture was stirred at room temperature overnight and concentrated under reduced pressure. The crude product was purified with flash column chromatography on silica gel (ethyl acetate in petroleum, 20% v/v) to furnish Compound 84B.1H-NMR (CDCl3, 400 MHz): delta (ppm) 1.40 (d, J = 4.8 Hz, 3H), 3.20 (d, J = 2.0 Hz, 1H), 3.23-3.25 (m, 1H), 3.78 (s, 3H).
	With sodium hexamethyldisilazane; In tetrahydrofuran; at -78℃; for 0.5h;Inert atmosphere;	General procedure: The title compound was prepared according to the General procedure C using 3-pyridinecarboxaldehyde as starting material. Y = 41 %. MS ES+: 194.1. NMR (300 MHz, Chloroform-) delta 8.67 - 8.59 (m, 2H), 7.63 - 7.54 (m, 1H), 7.39 - 7.28 (m, 1H), 4.44 - 4.24 (m, 2H), 4.16 (d, J= 2 Hz, 1H), 3.55 (d, J= 2 Hz, 1H), 1.36 (t, J= 7 Hz, 3H).

40
[ 75-03-6 ]
silver salt of/the/ β-phenyl-glycidic acid [ No CAS ]
[ 121-39-1 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1868,vol. 147,p. 84
Justus Liebigs Annalen der Chemie,1870,vol. 154,p. 168

41
[ 121-39-1 ]
sodium amalgam [ No CAS ]
[ 515-30-0 ]

Reference： [1]Chemische Berichte,1883,vol. 16,p. 2815

42
[ 121-39-1 ]
ammonium hydroxide [ No CAS ]
[ 151310-06-4 ]

Reference： [1],vol. 19,p. 1238
Chemisches Zentralblatt,1929,vol. 100,p. 1398

43
[ 110-91-8 ]
[ 121-39-1 ]
(2R*,3R*)-ethyl 2-hydroxy-3-morpholino-3-phenylpropionate [ No CAS ]
(2S,3S)-3-Hydroxy-2-morpholin-4-yl-3-phenyl-propionic acid ethyl ester [ No CAS ]

Reference： [1]Organic Letters,2000,vol. 2,p. 3555 - 3557
[2]Organic Letters,2000,vol. 2,p. 3555 - 3557

44
[ 92-54-6 ]
[ 121-39-1 ]
(2R*,3R*)-ethyl 2-hydroxy-3-(4-phenylpiperazino)-3-phenylpropionate [ No CAS ]
(2S,3S)-3-Hydroxy-3-phenyl-2-(4-phenyl-piperazin-1-yl)-propionic acid ethyl ester [ No CAS ]

Reference： [1]Organic Letters,2000,vol. 2,p. 3555 - 3557
[2]Organic Letters,2000,vol. 2,p. 3555 - 3557

45
[ 121-39-1 ]
[ 124-02-7 ]
(2S,3S)-2-Diallylamino-3-hydroxy-3-phenyl-propionic acid ethyl ester [ No CAS ]
(2R*,3R*)-ethyl 3-diallylamino-2-hydroxy-3-phenylpropionate [ No CAS ]

Reference： [1]Organic Letters,2000,vol. 2,p. 3555 - 3557
[2]Organic Letters,2000,vol. 2,p. 3555 - 3557

46
[ 121-39-1 ]
[ 103-49-1 ]
[ 134936-19-9 ]
(2R*,3R*)-ethyl 3-dibenzylamino-2-hydroxy-3-phenylpropionate [ No CAS ]

Reference： [1]Organic Letters,2000,vol. 2,p. 3555 - 3557
[2]Organic Letters,2000,vol. 2,p. 3555 - 3557

47
[ 121-39-1 ]
[ 98-59-9 ]
[ 50468-24-1 ]

Reference： [1]Chemistry Letters,2003,vol. 32,p. 82 - 83

48
[ 121-39-1 ]
(2,3-trans)-3-phenyloxirane-2-carboxylate [ No CAS ]
cis-ethyl-phenyl-glycidate [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4775 - 4777

49
[ 4192-77-2 ]
[ 121-39-1 ]
[ 4610-69-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 2025 - 2029

50
[ 121-39-1 ]
ethyl (+/-)-(αRS,βRS)-β-chloro-α-hydroxybenzenepropanoate [ No CAS ]
ethyl (+/-)-(αRS,βSR)-β-chloro-α-hydroxybenzenepropanoate [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2003,vol. 86,p. 2028 - 2057

51
[ 75-77-4 ]
[ 121-39-1 ]
[ 35153-45-8 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2003,vol. 178,p. 2545 - 2550

52
[ 121-39-1 ]
[ 74-85-1 ]
[ 124-38-9 ]
[ 122-78-1 ]

Reference： [1]Journal of Physical Organic Chemistry,2004,vol. 17,p. 694 - 698

53
[ 121-39-1 ]
[ 129867-27-2 ]

54
[ 121-39-1 ]
[ 67-64-1 ]
2,2-dimethyl-5-phenyl-[1,3]dioxolane-4-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Synlett,2005,p. 854 - 856

55
[ 121-39-1 ]
[ 64-17-5 ]
ethyl 3-phenyl-3-ethoxy-2-hydroxy propionate [ No CAS ]
[ 4192-77-2 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 4118 - 4123

56
[ 109-83-1 ]
[ 121-39-1 ]
N-(2-hydroxyethyl)-N-methyl-(2,3-trans)-3-phenyloxirane-2-carboxamide [ No CAS ]

Reference： [1]Synthesis,2005,p. 2549 - 2561

57
[ 68579-60-2 ]
[ 121-39-1 ]
N-(2-hydroxy-2-phenylethyl)-N-methyl-(2,3-trans)-3-phenyloxirane-2-carboxamide [ No CAS ]

Reference： [1]Synthesis,2005,p. 2549 - 2561

58
[ 121-39-1 ]
[ 21651-83-2 ]
(2,3-trans)-N-[(1R,2R)-2-hydroxycyclohexyl]-N-methyl-3-phenyloxirane-2-carboxamide [ No CAS ]

Reference： [1]Synthesis,2005,p. 2549 - 2561

59
[ 121-39-1 ]
[ 21651-84-3 ]
[ 680231-06-5 ]

Reference： [1]Synthesis,2005,p. 2549 - 2561

60
[ 121-39-1 ]
[ 84773-28-4 ]
[ 680230-90-4 ]

Reference： [1]Synthesis,2005,p. 2549 - 2561

61
[ 121-39-1 ]
[ 141-43-5 ]
N-(2-hydroxyethyl)-(2,3-trans)-3-phenyloxirane-2-carboxamide [ No CAS ]

Reference： [1]Synthesis,2005,p. 2549 - 2561

62
[ 121-39-1 ]
[ 7568-93-6 ]
N-(2-hydroxy-2-phenylethyl)-(2,3-trans)-3-phenyloxirane-2-carboxamide [ No CAS ]

Reference： [1]Synthesis,2005,p. 2549 - 2561

63
[ 121-39-1 ]
[ 882-33-7 ]
2-hydroxy-3-phenyl-3-phenylsulfanyl propionic acid ethyl ester [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,2006,vol. 84,p. 762 - 770

64
[ 121-39-1 ]
[ 89-64-5 ]
erythro ethyl 2-hydroxy-3-(4-chloro-2-nitrophenoxy)-3-phenylpropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With sodium hydride; In ethanol; for 3h;Heating / reflux;	a. erythro Ethyl 2-hydroxy-3-(4-chIoro-2-nitrophenoxy)-3-phenvIpropanoate (56a)To a stirred mixture of 4-chloro-2-nitrophenol (11.68g, 67.32 mmol), ethyl 3- phenyloxirane-2-carboxylate (9.61g, 50.00 mmol) in ethanol (200 mL) was added portionwise 60% sodium hydride (738 mg, 20.00 mmol) and the red mixture stirred at reflux for 3 d. The solvent was removed in vacuo. The residue was dissolved in CHCl3 and extracted three times with 10% aqueous potassium carbonate. The organic layer was washed with water and brine, dried, filtered and evaporated to afford a brown residue. The residue was dissolved in a minimal volume of CHCl3 and precipitated by adding diethyl ether to afford the title compound (5.970 g, 33%) as an off-white solid. 1K NMR (300 MHz, DMSO-d6) 61.16 (t, 3H, J= 7.0 Hz), 4.09 (q, 2H, J= 7.0 Hz), 4.29 (t, IH, J= 7.0 Hz), 5.63 (d, IH, J= 7.0 Hz), 6.09 (d, IH, J= 7.0 Hz), 7.19- 7.60 (m, 7H), 7.97 (d, IH, J= 2.6 Hz). MS APCI, m/z =388 (M+Na). LC/MS: 2.78 min.

Reference： [1]Patent: WO2007/104933,2007,A1 .Location in patent: Page/Page column 118

65
[ 121-39-1 ]
[ 1568-70-3 ]
erythro ethyl 2-hydroxy-3-(4-methoxy-2-nitrophenoxy)-3-phenylpropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With sodium hydride; In ethanol; for 216h;Heating / reflux;	a. erythro Ethyl 2-hydroxy-3-(4-methoxy-2-nitrophenoxy)-3-phenylpropanoate (68a)To a stirred mixture of 4-methoxy-2-nitrophenol (11.87 g, 70 mmol), ethyl 3- phenyloxirane-2-carboxylate (10.39 g, 54 mmol) and ethanol (175 niL) was added portionwise 60% sodium hydride (0.65 g, 16 mmol) and the red mixture stirred at reflux for 9 d. The solvent was removed in vacuo, the residue dissolved in EtOAc and extracted with 10% aqueous potassium carbonate. The organic layer was washed with water and brine, dried (MgSO4), filtered and the solvent stripped in-vacuo to yield an oil. Column chromatography (DCM then 5% methanol~DCM) afforded (9.5 g, 49%) of slightly impure title compound that was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) ?l.21 (t, 3H) 3.25 (d, IH, J=7.5 Hz) 3.77 (s, 3H), 4.20 (q, 2H) 4.67 (q, IH, J= 3.5, 7.5 Hz), 5.51 (d, IH, J=3.5 Hz), 6.82 (d, IH, J=9.2 Hz), 6.92 (dd, IH, J= 9.2, 3.0 Hz), 7.3-7.4 (m, 6H). HPLC (Method A): 3.24 min. b. erythro Ethyl 2-hvdroxy-3-(4-methoxy-2-nitrophenoxy)-3-phenyIpropanoate

Reference： [1]Patent: WO2007/104933,2007,A1 .Location in patent: Page/Page column 136

66
[ 121-39-1 ]
[ 6638-79-5 ]
(+/-)-N-methoxy-N-methyl-3-phenyloxirane-2-carboxamide [ No CAS ]