[ CAS No. 17857-14-6 ] {[proInfo.proName]}

Name: 17857-14-6|3-Carboxypropyltriphenylphosphonium bromide|97%
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Quality Control of [ 17857-14-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 17857-14-6 ]

Product Details of [ 17857-14-6 ]

CAS No. :	17857-14-6	MDL No. :	MFCD00274196
Formula :	C₂₂H₂₂BrO₂P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NKVJKVMGJABKHV-UHFFFAOYSA-N
M.W :	429.29	Pubchem ID :	10717451
Synonyms :

Calculated chemistry of [ 17857-14-6 ]

Physicochemical Properties

Num. heavy atoms :	26
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.14
Num. rotatable bonds :	7
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	116.13
TPSA :	50.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-1.59
Log Po/w (XLOGP3) :	5.45
Log Po/w (WLOGP) :	0.85
Log Po/w (MLOGP) :	5.13
Log Po/w (SILICOS-IT) :	4.77
Consensus Log Po/w :	2.92

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.99
Solubility :	0.000444 mg/ml ; 0.00000103 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.28
Solubility :	0.000228 mg/ml ; 0.00000053 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-8.09
Solubility :	0.00000346 mg/ml ; 0.0000000081 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	4.48

Safety of [ 17857-14-6 ]

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

Application In Synthesis of [ 17857-14-6 ]

* 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 [ 17857-14-6 ]
Downstream synthetic route of [ 17857-14-6 ]

[ 17857-14-6 ] Synthesis Path-Upstream 1~2

1
[ 2623-87-2 ]
[ 603-35-0 ]
[ 17857-14-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	for 48 h; Inert atmosphere; Reflux	General procedure: A mixture of ω-bromocarboxylic acid (1 equiv) and triphenylphosphine (1 equiv) in 300 mL of toluene was refluxed for 48 h under argon. The mixture was allowed to cool at room temperature and concentrated in vacuum. The residue was crystallized from various solvents to give the corresponding phosphonium salt.
89%	at 120℃; for 16 h; Inert atmosphere	General procedure: Triphenylphosphine (3.76g, 14.34mmol) and ethyl 4-bromobutyrate (2.0g, 10.25mmol) were added to a dried round bottom flask under argon. The reaction mixture was heated to 120°C under condenser for 16h after which the reaction was allowed to come to room temperature. CH₂Cl₂ (10mL) was added, followed by diethyl ether until no further precipitation of product was observed. The precipitate was further washed with ether (100mL) and dried in vacuo to give pure compound 2 as a white solid (4.64g) in quantitative yield.
74%	for 15 h; Reflux; Inert atmosphere	Compound 14 was synthesized according to the method of Yeung.¹ To a flame-dried 50 mL flask under argon equipped with a magnetic stirring bar was added a solution of γ-bromoacid 13 (2.50 g, 14.9 mmol, 1.00 eq.) in 20 mL of anhydrous acetonitrile. Solid triphenylphosphine (3.94 g, 14.9 mmol, 1.00 eq.) was added, the flask was equipped with a water-cooled condenser, and the reaction mixture was heated to reflux. Upon heating, all of the triphenylphosphine gradually dissolved to give an almost colorless solution; after 20 minutes, a white precipitate of the phosphonium started to form. After heating at reflux for 15 hours, the reaction mixture was allowed to cool slowly to room temperature. The precipitate was collected by vacuum filtration, washed with two 5 mL portions of cold acetonitrile, and dried under high vacuum to give pure phosphonium salt 14 (3.03 g, 47percent) as a fine white solid [mp 245–247.5 °C]. Evaporation of the filtrate afforded a yellow/orange solid that was triturated with a minimum amount of cold acetonitrile to give an additional 1.72 g (27percent) of 14 as a pale yellow powder.

64.2%

at 105℃; for 48 h;

Experimental procedure: Take a 250mL single-mouth round bottom flask,4-bromobutyric acid 1 (15.0 g, 1.0 eq) was added in succession.MeCN (120.0 mL) and triphenylphosphine (23.6 g, 1.0 eq).Heat to reflux, reflux temperature 105 °C,The reaction solution was a yellow liquid and reacted for about 2 days.Post-reaction treatment: The reaction system was directly filtered with a fritted funnel, washed with diethyl ether, and then vacuum-dried to obtain a white solid with a yield of 64.2percent.

Reference： [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5088 - 5102
[3] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2002, vol. 57, # 3, p. 335 - 337
[4] Tetrahedron Letters, 2016, vol. 57, # 10, p. 1083 - 1086
[5] Journal of the American Chemical Society, 2018, vol. 140, # 17, p. 5805 - 5813
[6] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 21, p. 5878 - 5881
[7] Patent: CN106946700, 2017, A, . Location in patent: Paragraph 0030; 0031; 0032
[8] Organic Letters, 2016, vol. 18, # 10, p. 2395 - 2398
[9] Journal of Organic Chemistry, 1989, vol. 54, # 17, p. 4224 - 4228
[10] Chemische Berichte, 1977, vol. 110, p. 3544 - 3552
[11] Journal of Organic Chemistry, 1991, vol. 56, # 13, p. 4196 - 4204
[12] Journal of Medicinal Chemistry, 1985, vol. 28, # 3, p. 287 - 294
[13] Journal of Medicinal Chemistry, 2008, vol. 51, # 12, p. 3487 - 3498
[14] Patent: US6753449, 2004, B2, . Location in patent: Page column 15
[15] Organic Letters, 2011, vol. 13, # 10, p. 2738 - 2741
[16] Angewandte Chemie - International Edition, 2012, vol. 51, # 9, p. 2187 - 2190
[17] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1718 - 1729
[18] Applied Catalysis A: General, 2014, vol. 470, p. 183 - 188
[19] Organic Letters, 2016, vol. 18, # 3, p. 504 - 507
[20] Organic Letters, 2017, vol. 19, # 18, p. 4940 - 4943
[21] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 275 - 284
[22] Patent: WO2018/106928, 2018, A1, . Location in patent: Page/Page column 29; 32

2
[ 96-48-0 ]
[ 6399-81-1 ]
[ 17857-14-6 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 4, p. 685 - 696
[2] Justus Liebigs Annalen der Chemie, 1967, vol. 709, p. 105 - 112

[ 17857-14-6 ] Synthesis Path-Downstream 1~57

1
[ 2623-87-2 ]
[ 603-35-0 ]
[ 17857-14-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	In toluene; for 48h;Inert atmosphere; Reflux;	General procedure: A mixture of omega-bromocarboxylic acid (1 equiv) and triphenylphosphine (1 equiv) in 300 mL of toluene was refluxed for 48 h under argon. The mixture was allowed to cool at room temperature and concentrated in vacuum. The residue was crystallized from various solvents to give the corresponding phosphonium salt.
89%	at 120℃; for 16h;Inert atmosphere;	General procedure: Triphenylphosphine (3.76g, 14.34mmol) and ethyl 4-bromobutyrate (2.0g, 10.25mmol) were added to a dried round bottom flask under argon. The reaction mixture was heated to 120C under condenser for 16h after which the reaction was allowed to come to room temperature. CH2Cl2 (10mL) was added, followed by diethyl ether until no further precipitation of product was observed. The precipitate was further washed with ether (100mL) and dried in vacuo to give pure compound 2 as a white solid (4.64g) in quantitative yield.
84%	In N,N-dimethyl-formamide; at 110℃; for 72h;	Triphenylphosphine (222 mg 0.16 mmol) and 4-Bromobutyric acid (70 mg 0.37 mmol) are dissolved in 100 mL N,N-dimethyl formamide (DMF). The mixture is kept stirring at 110 C for 72 h, and the reaction mixture is then filtered to acquire white solid (TPP-COOH) (yield: 84%). 1H NMR (400 MHz, DMSO-d6) delta 12.35 (s, 1H), 8.02-7.56 (m, 15H), 3.60 (td, J = 13.5, 7.7 Hz, 2H), 2.56-2.36 (m, 2H), 1.70 (td, J = 11.7, 9.7, 5.9 Hz, 2H).

74%	In acetonitrile; for 15h;Reflux; Inert atmosphere;	Compound 14 was synthesized according to the method of Yeung.1 To a flame-dried 50 mL flask under argon equipped with a magnetic stirring bar was added a solution of gamma-bromoacid 13 (2.50 g, 14.9 mmol, 1.00 eq.) in 20 mL of anhydrous acetonitrile. Solid triphenylphosphine (3.94 g, 14.9 mmol, 1.00 eq.) was added, the flask was equipped with a water-cooled condenser, and the reaction mixture was heated to reflux. Upon heating, all of the triphenylphosphine gradually dissolved to give an almost colorless solution; after 20 minutes, a white precipitate of the phosphonium started to form. After heating at reflux for 15 hours, the reaction mixture was allowed to cool slowly to room temperature. The precipitate was collected by vacuum filtration, washed with two 5 mL portions of cold acetonitrile, and dried under high vacuum to give pure phosphonium salt 14 (3.03 g, 47%) as a fine white solid [mp 245-247.5 C]. Evaporation of the filtrate afforded a yellow/orange solid that was triturated with a minimum amount of cold acetonitrile to give an additional 1.72 g (27%) of 14 as a pale yellow powder.
64.2%	With acetonitrile; at 105℃; for 48h;	Experimental procedure: Take a 250mL single-mouth round bottom flask,4-bromobutyric acid 1 (15.0 g, 1.0 eq) was added in succession.MeCN (120.0 mL) and triphenylphosphine (23.6 g, 1.0 eq).Heat to reflux, reflux temperature 105 C,The reaction solution was a yellow liquid and reacted for about 2 days.Post-reaction treatment: The reaction system was directly filtered with a fritted funnel, washed with diethyl ether, and then vacuum-dried to obtain a white solid with a yield of 64.2%.
	In tetrahydrofuran; for 72h;Heating / reflux;	Triphenyl phosphine (26.5 g, 100.4 mmol) was added to a solution of 4-bromobutyric acid (13.5 g, 105.4 mmol) in 200 ml dry THF and refluxed for 3 days. The solvent was removed and the residue was dissolved in 400 ml DMSO. Potassium t-butoxide (1M/THF, 200 ml, 200 mmol) was added to the above solution of (3- carboxypropyl) triphenylphosphonium bromide (about 100 mmol based on complete conversion in the first step) and the mixture was stirred at room temperature for 1 hr. Polystyrene-benzaldehyde (from Argonaut Technologies, 1.29 mmol/g, 25 g, predried in vacuum at 50 C. for 15 hrs) was added, and the mixture was heated at 100 C. overnight. The solvents were removed and the resin was washed with 2×200 ml each of methanol, water, methanol and THF. The above resin was suspended in 300 ml 10% conc. HCl in THF and stirred at room temperature for 1 hour. The solvent was removed by filtration and the resin was washed with THF and dried in vacuum at 50 C. for 15 hrs to give the functionalized resin 6.
	In toluene; for 24h;Reflux;	General procedure: A typical procedure for the preparation of [Ph3PC2H4NH2]Br (1c) is as follows: A solution of triphenylphosphine (5 mmol) and 2-bromoethylamine hydrobromide (5 mmol) in 20 mL toluene was heated and subject to reflux for 24 h. After cooling, the resulted crude solid was filtered out, and stirred in 10 mL triethylamine for 4 h. Afterward, the triethylamine was removed, and the as obtained solid was washed three times with ethyl acetate, then dried at 60 C under vacuum for 12 h to give product 1c in the form of a pale yellow solid.
	In acetonitrile; for 15h;Reflux;	General procedure: To a round-bottom flask was added 5a (5.0?mmol), P(Ph)3 (20.0?mmol) and dry MeCN (10.0?mL). The mixture was stirred vigorously and heated to reflux. After the refluxing was ceased (15?h), the solution was concentrated. The residue was rinsed consecutively with benzene (3?x?10?mL), hexanes (10?mL), and ether (2?x?10?mL). The crystalline white solid was dried to give 6a (1.8?g, 87%) [26] 6b-d were prepared according to the procedure described as 6a.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 567 - 579
[2]Organic and Biomolecular Chemistry,2019,vol. 17,p. 4572 - 4592
[3]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5088 - 5102
[4]Journal of Controlled Release,2020,vol. 322,p. 157 - 169
[5]Zeitschrift fur Naturforschung, B: Chemical Sciences,2002,vol. 57,p. 335 - 337
[6]Tetrahedron Letters,2016,vol. 57,p. 1083 - 1086
[7]Journal of the American Chemical Society,2018,vol. 140,p. 5805 - 5813
[8]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5878 - 5881
[9]Patent: CN106946700,2017,A .Location in patent: Paragraph 0030; 0031; 0032
[10]Organic Letters,2016,vol. 18,p. 2395 - 2398
[11]Journal of Organic Chemistry,1989,vol. 54,p. 4224 - 4228
[12]Chemische Berichte,1977,vol. 110,p. 3544 - 3552
[13]Journal of Organic Chemistry,1991,vol. 56,p. 4196 - 4204
[14]Journal of Medicinal Chemistry,1985,vol. 28,p. 287 - 294
[15]Journal of Medicinal Chemistry,2008,vol. 51,p. 3487 - 3498
[16]Patent: US6753449,2004,B2 .Location in patent: Page column 15
[17]Organic Letters,2011,vol. 13,p. 2738 - 2741
[18]Angewandte Chemie - International Edition,2012,vol. 51,p. 2187 - 2190
[19]Journal of Organic Chemistry,2013,vol. 78,p. 1718 - 1729
[20]Applied Catalysis A: General,2014,vol. 470,p. 183 - 188
[21]Organic Letters,2016,vol. 18,p. 504 - 507
[22]Organic Letters,2017,vol. 19,p. 4940 - 4943
[23]European Journal of Medicinal Chemistry,2018,vol. 155,p. 275 - 284
[24]Patent: WO2018/106928,2018,A1 .Location in patent: Page/Page column 29; 32
[25]Journal of Materials Chemistry B,2018,vol. 6,p. 8137 - 8147

2
[ 6221-04-1 ]
[ 17857-14-6 ]
(E)-5-[5-((E)-4-Carboxy-but-1-enyl)-pyridin-3-yl]-pent-4-enoic acid [ No CAS ]
[ 791-28-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 98% 2: 0.278 g	With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 50℃; for 28h;

Reference： [1]Baldwin, Jack E.; Cameron, James H.; Crossley, Maxwell J.; Dagley, Ian J. [Journal of the Chemical Society, Dalton Transactions, 1984, p. 1739 - 1746]

3
[ 17857-14-6 ]
[ 100-52-7 ]
[ 28525-69-1 ]
[ 17920-83-1 ]

Yield	Reaction Conditions	Operation in experiment
58%		Compound 15 was synthesized according to the method of Yeung.1 To a flame-dried 100 mL flask under argon equipped with a magnetic stirring bar was added phosphonium salt 14 (2.75 g, 6.41 mmol, 1.10 eq.) and 25 mL of anhydrous THF. This suspension was cooled to -60 C, and a 2 M solution of sodium bis(trimethylsilyl)amide (NaHMDS, 6.41 mL, 2.20 eq.) was added dropwise over five minutes. At the end of the addition, all of the solid had dissolved, and the reaction mixture was dark orange. After stirring for 30 minutes at -60 C, neat benzaldehyde (590 muL, 5.82 mmol, 1.00 eq.) was added dropwise, discharging the orange color to yellow. After 20 minutes, the resulting yellow suspension was allowed to warm slowly to room temperature and stirred for 15 hours. Water (50 mL) and Et2O (50 mL) were then added, and the mixture was stirred vigorously until all of the solids had dissolved. The layers were separated, and the aqueous phase was washed with two additional 50 mL portions of Et2O in order to remove as much of the triphenylphosphine oxide byproduct as possible. The aqueous layer was then acidified to pH ? 1 using 3 M aqueous HCl solution, resulting in the formation of a fine white precipitate. Ethyl acetate (25 mL) was added to dissolve the solid, and the layers were separated. The aqueous phase was extracted with three additional 25 mL portions of EtOAc, and the combined organic layers were dried over anhydrous Na2SO4. TLC of the crude mixture (1:1 hexanes / EtOAc, UV / anisaldehyde) showed clean formation of the product of Rf = 0.27. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (1:1 hexanes / EtOAc) to give styrene 15 (982 mg, 87%) as a white solid. 1H-NMR showed that 15 had been formed as a ~9:1 mixture of E/Z isomers. Trituration with two 10 mL portions of cold hexanes afforded pure (E)-15 (654 mg, 58%) as flaky white crystals [mp 86-88 C].

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 1083 - 1086
[2]Phosphorus and Sulfur and the Related Elements,1983,vol. 18,p. 187 - 190

4
[ 17857-14-6 ]
[ 123-11-5 ]
[ 5724-06-1 ]

Yield	Reaction Conditions	Operation in experiment
73%		To a solution of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (1.1 g, 2.5 mmol, 1.2 eq.) in tetrahydrofuran (10 ml) was added dropwise a solution of sodium bis(trimethylsilyl)amide (1.0 M in tetrahydrofuran, 5.0 ml, 5.0 mmol, 2.4 eq.) at 0 C. The solution was stirred for 30 min, then cooled to -78 C. P-anisaldehyde (0.25 ml, 2.0 mmol, 1 eq.) was then added dropwise. The reaction was allowed to warm to room temperature overnight. Water and ether were added. The water layer was separated and acidied with 1 M aqueous hydrochloric acid to pH = 1, then extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (1:1 to 5:1 ether:hexanes) to give 0.31 g of product (73%) as a white solid.

Reference： [1]Organic Letters,2016,vol. 18,p. 5880 - 5883
[2]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1630 - 1636
[3]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 1649 - 1674
[4]Organic Letters,2011,vol. 13,p. 2738 - 2741
[5]Organic Letters,2016,vol. 18,p. 5256 - 5259

5
[ 17857-14-6 ]
[ 857480-35-4 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7351 - 7362
[2]Patent: WO2012/18325,2012,A1
[3]Patent: WO2012/151137,2012,A1
[4]Patent: WO2015/89337,2015,A1
[5]Patent: WO2015/89327,2015,A1
[6]Patent: WO2018/191577,2018,A1
[7]Patent: WO2020/43638,2020,A1

6
4aR-(4aα,5β,8β,8aβ)]-octahydro-5,8-epoxy-1H-2 -benzopyran-3-ol [ No CAS ]
[ 41233-93-6 ]
[ 17857-14-6 ]
[1S-[1α,2α(Z),3α,4α]]-6-[3-hydroxymethyl)-7-oxabicyclo[2.2.1]hept-2 -yl]-4-hexenoic acid [ No CAS ]
[ 791-28-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium chloride; In tetrahydrofuran; water; potassium carbonate; acetic acid; ethyl acetate; toluene;	C. 1S-[1alpha,2alpha(Z),3alpha,4alpha]]-6-[3-(Hydroxy-methyl)-7-oxabicyclo[2.2.1]hept-2 -yl]-4-hexenoic acid, methyl ester To a partial solution of 36.27 g of 4aR-(4aalpha,5beta,8beta,8abeta)]-octahydro-5,8-epoxy-1H-2 -benzopyran-3-ol (prepared as described in U.S. Pat. No. 4,143,054) (0.23 mol) and 3-carboxypropyl-triphenylphosphonium bromide (127.34 g, 0.37 mol) in 600 mL of dry THF under argon at 3 C. was added dropwise over 1 hour a solution of 370.6 mL of potassium t-amylate (0.68 mol of a 1.8M toluene solution) with mechanical stirring. Initially the reaction temperature reached a maximum of 8 C. and subsequently leveled off to 4 C. for the remainder of the base addition. The reaction was then run at room temperature for 90 minutes. A 0 C. ice bath was introduced and the reaction was quenched by the addition of 152 mL of glacial acetic acid, over 30 minutes. Solvents were removed in vacuo (azeotroped with toluene). Water (640 mL) and 50 mL of concentrated HCl were added (pH 2.6). Dilution with 640 mL of ethyl acetate, the addition of 149 g of NaCl and a few seed crystals of 3-carboxypropyltriphenylphosphonium bromide was followed by vigorous stirring for 15 minutes. The precipitate was collected by filtration and washed with 2 portions each of 320 mL of ethyl acetate. The ethyl acetate layer was separated, the aqueous layer was extracted with ethyl acetate (2200 mL each), the combined ethyl acetate layers were dried over MgSO and concentrated. Aqueous 5% K2 CO3 was added (507 mL) followed by vigorous stirring for 1 hour. No precipitation occurred. The reaction mixture was concentrated to a paste and suspended in 508 mL of water. Several hours of vigorous stirring produced no precipitate. The water was decanted off and the residue was suspended in 200 mL of aqueous 5% K2 CO3 solution. After vigorous stirring, a light tan solid was collected by filtration and rinsed several times with water. The combined aqueous layers were extracted 5with 1:1 toluene/ether (230 mL each). After cooling the combined aqueous layers with a 0 C. ice bath, concentrated HCl was added to pH 2.5, followed by extraction 1 with 460 mL then 2with 230 mL each of ethyl acetate. The combined ethyl acetate layers were dried over MgSO4 and evaporated in vacuo to yield 49.74 of an amber oil. Trituration from 330 mL of ether (room temperature, overnight) oiled out phosphorous by-products. The ether solution was decanted away from the dark red oil into a separatory funnel, and the oil which was carried over by the decantation was drained off (1.56 g). Evaporation of the ether solution in vacuo yielded 43.08 g of [1S-[1alpha,2alpha(Z),3alpha,4alpha]]-6-[3-hydroxymethyl)-7-oxabicyclo[2.2.1]hept-2 -yl]-4-hexenoic acid in the form of a viscous yellow oil. 1 H NMR indicated a product: triphenylphosphine oxide: ether molar ratio of 23:1:1.8 (mass % 93:4.7:2.2). Yield exclusive of triphenylphosphine oxide/ether, 40.06 g (72.5%).

Reference： [1]Patent: US5100889,1992,A

7
C₁₆H₂₂O₄ [ No CAS ]
[ 17857-14-6 ]
C₂₀H₂₈O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%		(3-Carboxypropyl)triphenylphosphonium bromide was dried under vacuum at 100 C for 2-3h. To a stirred solution of (3-Carboxypropyl)triphenylphosphonium bromide (1.47g, 3.43 mmol) in dry Toluene (10 ml_), Potassium t-butoxide (0.774g, 6.89 mmol) was added in portions at room temperature under inert conditions. The mixture was heated to 8O0C and temperature was maintained for 30-40 min. Reaction mass was cooled to 50 C and the aldehyde (compound 6-12) (0.3g, 1.07 mmol) in dry THF (2 ml.) was added to above mixture drop wise. The progress of the reaction was monitored by TLC. After the completion of reaction, the mass was cooled to 0-5 C and quenched with 1 N HCI (1 ml.) by adjusting the pH 4-5. The compound was extracted with ethyl acetate (3 X 10 ml.) and separated the aqueous layer. The combined organic fractions were collected and dried over so- dium sulphate (2g), concentrated in vacuo. The crude product was purified by column chromatography to obtain compound 6-14 pure (ethyl acetate:hexanes; 2:8).Yield: 325 mg (86 %). <n="78"/>1H NMR (CDCI3, 300 MHz): delta 7.45-7.4 (d, J=IA Hz, 1 H), 7.25-7.10 (t, J=7.1 , 1 H), 6.95-6.85 (t, J=7.1 Hz, 1 H), 6.80-6.70 (d, J=7.1 Hz, 1 H), 5.40-5.30 (s, 1 H), 5.25-5.10 (m, 2H), 4.2-4.1 (d, J=14.3 Hz, 1 H), 3.85-3.8 (d, J=14.3 Hz, 1 H), 3.75 (s, 3H), 2.35-2.05 (m, 4H), 1.75-1.5 (m, 3H), 1.50-1.45 (d, J=11.4Hz, 6H), 0.85-0.75 (m, 2H). MW:371.1 (M++Na).

Reference： [1]Patent: WO2008/89461,2008,A1 .Location in patent: Page/Page column 74-75

8
C₁₂H₁₆O₄ [ No CAS ]
[ 17857-14-6 ]
C₁₆H₂₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		Wittig reaction employing racemic lactol-Synthesis of racemic diol (2-8): An amount of 191 g carboxypropyltriphenylphosphonium bromide, 1000 mL anhydrous toluene and 100g potassium t-butoxide were mixed at 80 C for 30 min. The mixture was cooled to room tem- perature. An amount of 25g purified racemic lactol (114.5 mmol) pre-dissolved in 180 mL anhydrous THF were slowly added. The reaction was continued for 60 min. The crude reaction mixture was poured into 1500 mL ice-water, 300 mL ethyl acetate were added. The aqueous phase was re-extracted with 300 mL ethyl acetate. The aqueous phase was then acidified with 2N HCI, and extracted 3 times using 300 mL ethyl acetate. The solids that had formed were filtered off. The organic phase was evaporated. To the evaporated residue were added 500 mL diethyl ether. The flask was swirled for 10 min, and the solids were filtered off. The filtrate was extracted 3 times with saturated sodium bicarbonate solution. The aqueous phase was then acidified to pH 4 using 2M HCI. The aqueous phase was then extracted 3 times employing 200 mL of ethyl acetate. The organic phases were combined, dried over MgSO4 and evaporated to yield 45g of materialColumn chromatography: Racemic diol was purified over silica gel (35 cm column length, 4 cm diameter). Racemic diol was dissolved in a minimum of ethyl acetate and applied to the column. 1 L of ethyl acetate (60%)/hexanes (40%) was added to a volumetric cylinder. 300 mL of EtOAc/hexanes was taken from the cylinder and added to the column. The remaining 700 mL of EtOAc/hexanes in the cylinder were diluted to 1 L using ethyl acetate. 300 mL of the new EtOAc/hexanes solution were then added to the column and were allowed to pass through the column. The remaining 700 mL of EtOAc /hexanes in the cylinder were again diluted to 1 L using ethyl acetate. 300 mL of the new EtOAc/hexanes solution were then added to the column and were allowed to pass through the column. The remaining 700 L of EtOAc/hexanes in the cylinder were diluted once more to 1 L using ethyl acetate. 300 mL of <n="58"/>the new EtOAc/hexanes solution were then added to the column and were allowed to pass through the column. Pure fractions of racemic diol were collected and evaporated to yield 26g of pure racemic diol.Yield: 26g (88.3 mmol, 79%)

Reference： [1]Patent: WO2008/89461,2008,A1 .Location in patent: Page/Page column 53; 55; 57

9
[ 19829-31-3 ]
[ 17857-14-6 ]
C₁₃H₁₅BrO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		19.3 g (44.9 mmol) of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> are dried under vacuum for 1 h and by heating 130 C. and then brought to room temperature and dissolved in 200 ml of anhydrous THF. 10.1 g (89.8 mmol) of potassium tert-butoxide in 100 ml of THF are then slowly added and then the orange-red mixture is stirred for 15 minutes. A solution of 6.4 g (29.9 mmol) of 1-(3-bromophenyl)propanone in 100 ml of THF is then added dropwise and the reaction medium is stirred for 15 hours. After treating with a saturated ammonium chloride solution and extracting with ethyl acetate and then drying and evaporating the solvents of the organic phase, the residue is purified by chromatography on a silica column. A yellow oil is obtained (m=6.2 g; Y=74%). This product is then dissolved in 100 ml of methanol and then 2 ml of sulphuric acid are added. The reaction medium is heated under reflux and stirred for 2 hours. After treating with water, the medium is extracted with ethyl acetate and then the organic phases are combined, dried and concentrated under reduced pressure. The residue is purified by chromatography on a silica column (eluent heptane 95-ethyl acetate 5) in order to obtain the pure trans isomer in the form of a yellow oil (m=6.5 g; Y=74% total).

Reference： [1]Patent: US6689922,2004,B1 .Location in patent: Page column 79

10
[ 5370-25-2 ]
[ 17857-14-6 ]
C₁₀H₁₁BrO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: (3-carboxypropyl)(triphenyl)phosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.25h; Stage #2: 2-Acetyl-5-bromothiophene In tetrahydrofuran for 15h;	1.c c) Ethyl (E)-5-(Bromo-2-thienyl)-4-hexenoate 22.2 g (51.7 mmol) of (3-carboxypropyl)triphenylphosphonium bromide are dried under vacuum for 1 h with heating at 130° C., and then cooled to room temperature and dissolved in 200 mL of anhydrous THF. 11.5 g (102.5 mmol) of potassium tert-butoxide in 100 mL of THF are then added slowly, after which the orange-red mixture is stirred for 15 minutes. A solution of 7 g (34 mmol) of 1-(5-bromo-2-thienyl)ethanone in 100 mL of THF is then added dropwise and the reaction medium is stirred for 15 hours. After treatment with saturated ammonium chloride solution, extraction with ethyl acetate, drying and evaporation of the solvents from the organic phase, the residue obtained is purified by chromatography on a column of silica. An ochre-coloured solid is obtained (m.p.: 62-64° C., m=5.8 g; Y=62%). This product is then dissolved in 100 mL of ethanol and 2 mL of sulphuric acid are then added. The reaction medium is brought to reflux and stirred for 2 hours. After treatment with water, the medium is extracted with ethyl acetate and the organic phases are then combined, dried and concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica (eluent: 95 heptane/5 ethyl acetate) to give the pure trans isomer in the form of a yellow oil (m=3.4 g; Y=77%).

Reference： [1]Current Patent Assignee: Galderma (in: EQT Partners); Eqt Partners AB - US6706725, 2004, B1 Location in patent: Page column 11

11
[ 99-88-7 ]
[ 17857-14-6 ]
[ 1144524-65-1 ]

Yield	Reaction Conditions	Operation in experiment
74%		Intermediate 140; (4-{r4-(1-methylethyl)phenv?amino)-4-oxobutyl)(triphenyl)phosphonium bromide; To a solution of HOBT (3.6 g, 26.6 mmol), EDAC (5.1 g, 26.6 mmol) and triethylamine (5.3 ml, 66.6 mmol) in DMF was added <strong>[17857-14-6](3-carboxypropyl)(triphenyl)phosphonium bromide</strong> (10.5 g, 24.4 mmol). The reaction mixture was stirred at room temperature for 15 min and 4-(1-methylethyl)aniline (3 g, 22.2 mmol) was added. The mixture was stirred at room temperature overnight. DMF was evaporated and the residue was diluted with dichloromethane and a saturated solution of NaHCO3. The organic phase was extracted, dried over Na2SO4, filtered and evaporated. The residue was purified on SiO2 eluting with <n="95"/>PB62659Cdichloromethane to dichloromethane/methanol 9/1. The obtained product was triturated in isopropyl ether and sonicated to give the title compound as a white product (9 g, 74%). NMR1H NMR (300 MHz), CDCI3 delta: 7.86 (m, 9H), 7.76 (m, 8 H), 7.21 (d, 2H, J=8.45 HZ), 3.82 (m, 2H), 3.1 1 (t, 2H, J=6.34 Hz), 2.92 (m, 1 H), 2.14 (m, 2H), 1.28 (d, 6H, J=7.08 H z).

Reference： [1]Patent: WO2009/47240,2009,A1 .Location in patent: Page/Page column 93-94

12
[ 17857-14-6 ]
[ 6334-18-5 ]
[ 847948-69-0 ]

Yield	Reaction Conditions	Operation in experiment
100%		a) 5-(2,3-Dichloro-phenyl)-pent-4-enoic acid (4a) (3-Carboxypropyl) triphenylphosphonium bromide (18.1 g, 42 mmol) was dissolved in anhydrous tetrahydrofuran (250 ml), treated dropwise with potassium tert-butoxide (92.4 mL, 1.0 M in tetrahydrofuran, 92.4 mmol) and stirred for 1.5 hours at 0 C. A solution of commercially available 2,3-dichlorobenzaldehyde (Aldrich Chemical Company) (5.25 g, 30 mmol) in tetrahydrofuran (50 ml) was added dropwise at 0 C., and the reaction mixture was stirred at room temperature overnight. The reaction was quenched with 1N HCl (150 ml) and extracted with ethyl acetate (3*200 ml). The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography over silica gel (hexane-ethyl acetate, 2:1) to give the title compound (7.30 g,~100%). 1H NMR (300 MHz, CDCl3) delta: 7.4-5.85 (m, 5H), 2.96-2.65 (m, 4H).

Reference： [1]Patent: US2005/54630,2005,A1 .Location in patent: Page/Page column 33

13
[ 124-19-6 ]
[ 17857-14-6 ]
[ 49580-60-1 ]

Yield	Reaction Conditions	Operation in experiment
82%		General procedure: To a stirring suspension of phosphonium salts (5a-e) (1 equiv) in THF (250 mL) was added slowly 40% solution of sodium hexamethyldisilylamide (2 equiv) THF at room temperature in argon and stirring continued for 2 h. Aldehyde (1 equiv) was dissolved in THF (25 mL) and introduced drop wise. The mixture was stirred for further 3 h and then poured into 150 mL of water to get a clear solution. The resulting solution was concentrated in vacuum and the residue was extracted with diethyl ether (3 x 250 mL). The aqueous layer was acidified with 10% HCl and extracted with ether (3 x 200 mL). The organic layer obtained from the aqueous extract was dried and concentrated to afford the corresponding unsaturated carboxylic acids (6a-m).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 567 - 579

14
[ 112-31-2 ]
[ 17857-14-6 ]
[ 7089-44-3 ]

Yield	Reaction Conditions	Operation in experiment
76%		General procedure: To a stirring suspension of phosphonium salts (5a-e) (1 equiv) in THF (250 mL) was added slowly 40% solution of sodium hexamethyldisilylamide (2 equiv) THF at room temperature in argon and stirring continued for 2 h. Aldehyde (1 equiv) was dissolved in THF (25 mL) and introduced drop wise. The mixture was stirred for further 3 h and then poured into 150 mL of water to get a clear solution. The resulting solution was concentrated in vacuum and the residue was extracted with diethyl ether (3 x 250 mL). The aqueous layer was acidified with 10% HCl and extracted with ether (3 x 200 mL). The organic layer obtained from the aqueous extract was dried and concentrated to afford the corresponding unsaturated carboxylic acids (6a-m).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 567 - 579

15
[ 111-71-7 ]
[ 17857-14-6 ]
[ 49580-59-8 ]

Yield	Reaction Conditions	Operation in experiment
87%		General procedure: To a stirring suspension of phosphonium salts (5a-e) (1 equiv) in THF (250 mL) was added slowly 40% solution of sodium hexamethyldisilylamide (2 equiv) THF at room temperature in argon and stirring continued for 2 h. Aldehyde (1 equiv) was dissolved in THF (25 mL) and introduced drop wise. The mixture was stirred for further 3 h and then poured into 150 mL of water to get a clear solution. The resulting solution was concentrated in vacuum and the residue was extracted with diethyl ether (3 x 250 mL). The aqueous layer was acidified with 10% HCl and extracted with ether (3 x 200 mL). The organic layer obtained from the aqueous extract was dried and concentrated to afford the corresponding unsaturated carboxylic acids (6a-m).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 567 - 579

16
[ 112-44-7 ]
[ 17857-14-6 ]
[ 64252-91-1 ]

Yield	Reaction Conditions	Operation in experiment
87%		General procedure: To a stirring suspension of phosphonium salts (5a-e) (1 equiv) in THF (250 mL) was added slowly 40% solution of sodium hexamethyldisilylamide (2 equiv) THF at room temperature in argon and stirring continued for 2 h. Aldehyde (1 equiv) was dissolved in THF (25 mL) and introduced drop wise. The mixture was stirred for further 3 h and then poured into 150 mL of water to get a clear solution. The resulting solution was concentrated in vacuum and the residue was extracted with diethyl ether (3 x 250 mL). The aqueous layer was acidified with 10% HCl and extracted with ether (3 x 200 mL). The organic layer obtained from the aqueous extract was dried and concentrated to afford the corresponding unsaturated carboxylic acids (6a-m).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 567 - 579

17
[ 19009-56-4 ]
[ 17857-14-6 ]
[ 1331666-63-7 ]

Yield	Reaction Conditions	Operation in experiment
		A.I A stereoisomeric mixture of the preferred compound of the invention, 6-methyl myristic acid monoglyceride, was synthesized according to Scheme A.Racemic 2-methyldecanal [19009-56-4] was thus allowed to react withtriphenylposphonium butanoic acid bromide [17857-14-6] to afford after purification 6-methyl- 4-ene-tetradecanoic acid. The analogous acid chloride was prepared with thionyl chloride and treated directly with racemic isopropylidene glycerol then subjected to hydrogenation. The isopropylidene was removed with HCl to obtain 6-methyl myristate 1-glyceride as a mixture of stereoisomers.

Reference： [1]Current Patent Assignee: UNITED PARAGON ASSOCIATES; UNITED PARAGON ASS - WO2011/29099, 2011, A1 Location in patent: Page/Page column 22-24

18
[ 17857-14-6 ]
[ 100-52-7 ]
[ 28525-69-1 ]

Yield	Reaction Conditions	Operation in experiment
95%		To a solution of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (1.9 g, 4.5 mmol, 1.1 eq.) in tetrahydrofuran (20 ml) was added dropwise a solution of sodium bis(trimethylsilyl)amide (1.0 M in tetrahydrofuran, 9.0 ml, 9.0 mmol, 2.2 eq.) at 0 cC. The solution was stirred for 30 min, then cooled to -78 C. Benzaldehyde (0.42 ml, 4.2 mmol, 1 eq.) was then added dropwise. The reaction was allowed to warm to room temperature overnight. Water and ether were added. The water layer was separated and acidied with 1 M aqueous hydrochloric acid to pH = 1, then extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was chromatographed on silica gel (3:1 ether:hexanes) to give 0.70 g of product (95%) as a white solid.
91%		General procedure: Under Ar atmosphere, to a solution of (Me3Si)2NH (25.2 mL, 120 mmol) in THF (58 mL) was added n-BuLi (1.64M in hexane, 67 mL, 110 mmol) dropwise over 5 min at 0 C, and the mixture was stirred for 30 min at the same temperature. The resulting LiHMDS solution was added to a suspension of (4-carboxybutyl)triphenylphosphonium bromide (22.2 g, 50 mmol) at room temperature, and the mixture was stirred for 1 h. Benzaldehyde (5.0 mL, 50 mmol) was added and the whole was stirred at room temperature for 24 h. The reaction was quenched by an addition of water (300 mL), and the separated aqueous layer was washed with Et2O (600 + 400 mL). The resulting aqueous layer was acidified with conc. HCl (4 mL) to pH 3, and then extracted with EtOAc (600 400 mL). The combined EtOAc extracts were dried over Na2SO4 and concentrated. Column chromatography (SiO2 300 g, hexane/EtOAc 1/1) gave 8a (8.58 g, 90%, E/Z 9/1) as a yellow oil.

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1630 - 1636
[2]Tetrahedron,2018,vol. 74,p. 5309 - 5318
[3]Organic Letters,2011,vol. 13,p. 2738 - 2741
[4]Organic Letters,2016,vol. 18,p. 5256 - 5259
[5]Advanced Synthesis and Catalysis,2019,vol. 361,p. 1792 - 1797

19
[ 17857-14-6 ]
[ 1122-91-4 ]
[ 1300698-86-5 ]

Yield	Reaction Conditions	Operation in experiment
62.8%		To a solution of 3-carboxypropyltriphenylphosphonium bromide (15 g, 34.9 mmol) in DMSO (30 mL) was added KOtBu (1 M solution in THF) (73.4 mL, 73.4mmol) at rt, during which time a slight exotherm was observed. After stirring for 40 mm at rt, 4-bromobenzaldehyde (6.46 g, 34.9 mmol) was added slowly. The reaction mixture was stirred at rt for 16 h, then was quenched with water (200 mL), then washed with EtOAc/hexanes(1: 1). The aqueous layer was neutralized with conc. aq. HC1 (pH = 2), then extracted with EtOAc. The organic layer was concentrated in vacuo and the residuewas chromatographed (Si02 160 g, continuous gradient from 100% hexanes-100% EtOAc) to afford the title compound (5.6 g, 21.95 mmol, 62.8% yield). 1H NMR (500MHz, CDC13) oe 7.48 - 7.40 (m, 2H), 7.26 - 7.20 (m, 2H), 6.48 - 6.36 (m, 1H), 6.30 - 6.15 (m, 1H), 2.61 -2.53 (m, 4H).

Reference： [1]Patent: WO2016/40225,2016,A1 .Location in patent: Paragraph 00249
[2]Organic Letters,2011,vol. 13,p. 2738 - 2741
[3]Advanced Synthesis and Catalysis,2019,vol. 361,p. 1792 - 1797

20
[ 17857-14-6 ]
[ 591-31-1 ]
[ 1300698-81-0 ]

Yield	Reaction Conditions	Operation in experiment
91%		To a solution of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (2.0 g, 4.8 mmol, 1.1 eq.) in tetrahydrofuran (20 ml) was added dropwise a solution of lithium bis(trimethylsilyl)amide (1.0 M in tetrahydrofuran, 9.5 ml, 9.5 mmol, 2.2 eq.) at 0 C. The solution was stirred for 30 min, then cooled to -78 C. M-anisaldehyde (0.54 ml, 4.4 mmol, 1 eq.) was then added dropwise. The reaction was allowed to warm to room temperature overnight. Water and ether were added. The water layer was separated and acidied with 1 M aqueous hydrochloric acid to pH = 1, then extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (3:1 ether:hexanes) to give 0.83 g of product (91%) as a white solid.
53%		A solution of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (31 .47 g,73.52 mmol) in THF (200 ml) was treated with potassium tert-butoxide (20.58 g,18.37 mmol) and stirred at rt for 1 h under argon. 3-Methoxybenzaldehyde (10 g,73.52 mmol) was added then the mixture was stirred at the same temperature for 16h.The reaction mixture was cooled to 0C,acidified to pH = 2 by HCI (2 N) and extracted with EtOAc (2 x 500ml). The combined organic layers were dried over Na2S04 and concentrated under reduced pressure. The crude compound was purified by column chromatography (silica gel 100-200 mesh) using 0-70% EtOAc in petroleum ether as an eluent to give the title compound 1f-1 as a yellow gummy liquid (8 g,53% yield). LCMS [M+H]+ 207.

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1630 - 1636
[2]Patent: WO2019/109188,2019,A1 .Location in patent: Paragraph 00237
[3]Organic Letters,2011,vol. 13,p. 2738 - 2741
[4]Organic Letters,2016,vol. 18,p. 5256 - 5259

21
C₁₂H₁₆O₄ [ No CAS ]
[ 17857-14-6 ]
C₁₆H₂₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		An amount of 191 g carboxypropyltriphenylphosphonium bromide, 1000 mL anhydrous toluene and 100 g potassium t-butoxide were mixed at 80 C. for 30 min. The mixture was cooled to room temperature. An amount of 25 g purified racemic lactol (114.5 mmol) pre-dissolved in 180 mL anhydrous THF were slowly added. The reaction was continued for 60 min. The crude reaction mixture was poured into 1500 mL ice-water, 300 mL ethyl acetate were added. The aqueous phase was re-extracted with 300 mL ethyl acetate. The aqueous phase was then acidified with 2N HCl, and extracted 3 times using 300 mL ethyl acetate. The solids that had formed were filtered off. The organic phase was evaporated. To the evaporated residue were added 500 mL diethyl ether. The flask was swirled for 10 min, and the solids were filtered off. The filtrate was extracted 3 times with saturated sodium bicarbonate solution. The aqueous phase was then acidified to pH 4 using 2M HCl. The aqueous phase was then extracted 3 times employing 200 mL of ethyl acetate. The organic phases were combined, dried over MgSO4 and evaporated to yield 45 g of materialColumn chromatography: Racemic diol was purified over silica gel (35 cm column length, 4 cm diameter). Racemic diol was dissolved in a minimum of ethyl acetate and applied to the column. 1 L of ethyl acetate (60%)/hexanes (40%) was added to a volumetric cylinder. 300 mL of EtOAc/hexanes was taken from the cylinder and added to the column. The remaining 700 mL of EtOAc/hexanes in the cylinder were diluted to 1 L using ethyl acetate. 300 mL of the new EtOAc/hexanes solution were then added to the column and were allowed to pass through the column. The remaining 700 mL of EtOAc/hexanes in the cylinder were again diluted to 1 L using ethyl acetate. 300 mL of the new EtOAc/hexanes solution were then added to the column and were allowed to pass through the column. The remaining 700 L of EtOAc/hexanes in the cylinder were diluted once more to 1 L using ethyl acetate. 300 mL of the new EtOAc/hexanes solution were then added to the column and were allowed to pass through the column. Pure fractions of racemic diol were collected and evaporated to yield 26 g of pure racemic diol.Yield: 26 g (88.3 mmol, 79%)

Reference： [1]Patent: US2011/178112,2011,A1 .Location in patent: Page/Page column 13; 14

22
C₁₆H₂₂O₄ [ No CAS ]
[ 17857-14-6 ]
C₂₀H₂₈O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%		(3-Carboxypropyl)triphenylphosphonium bromide was dried under vacuum at 100 C. for 2-3 h. To a stirred solution of (3-Carboxypropyl)triphenylphosphonium bromide (1.47 g, 3.43 mmol) in dry Toluene (10 mL), Potassium ter-butoxide (0.774 g, 6.89 mmol) was added in portions at room temperature under inert conditions. The mixture was heated to 80 C. and temperature was maintained for 30-40 mins. Reaction mass was cooled to 50 C. and the aldehyde (compound 6-12) (0.3 g, 1.07 mmol) in dry THF (2 mL) was added to above mixture drop wise. The progress of the reaction was monitored by TLC. After the completion of reaction, the mass was cooled to 0-5 C. and quenched with 1 N HCl (1 mL) by adjusting the pH 4-5. The compound was extracted with ethyl acetate (3×10 mL) and separated the aqueous layer. The combined organic fractions were collected and dried over sodium sulphate (2 g), concentrated on vacuo. The crude product was purified by column chromatography to obtain compound 6-14 in pure (ethyl acetate:hexanes; 2:8).Yield: 325 mg (86%).1H NMR (CDCl3, 300 MHz): delta 7.45-7.4 (d, J=7.1 Hz, 1H), 7.25-7.10 (t, J=7.1, 1H), 6.95-6.85 (t, J=7.1 Hz, 1 H), 6.80-6.70 (d, J=7.1 Hz, 1H), 5.40-5.30 (s, 1H), 5.25-5.10 (m, 2H), 4.2-4.1 (d, J=14.3 Hz, 1H), 3.85-3.8 (d, J=14.3 Hz, 1H), 3.75 (s, 3H), 2.35-2.05 (m, 4H), 1.75-1.5 (m, 3H), 1.50-1.45 (d, J=11.4 Hz, 6H), 0.85-0.75 (m, 2H).Mass:371.1 (M++Na).

Reference： [1]Patent: US2011/178112,2011,A1 .Location in patent: Page/Page column 24-26

23
[ 1016-78-0 ]
[ 17857-14-6 ]
5-(3-chlorophenyl)-5-phenylpent-4-enoic acid [ No CAS ]

Reference： [1]Organic Letters,2011,vol. 13,p. 6504 - 6507

24
[ 3132-99-8 ]
[ 17857-14-6 ]
[ 1180670-58-9 ]

Yield	Reaction Conditions	Operation in experiment
90%		In a 250-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, to a solution of (3- carboxypropyl)triphenylphosphanium bromide (23.26 g, 51.5 mmol, 1.00 equiv) in DMSO (200 mL) was added sodium hydride (60% in oil, 5.4 g, 135.0 mmol, 2.63 equiv ) at 0 C. The resulting mixture was stirred for 1 h at 25 C, and then was added by 3-bromobenzaldehyde (10 g, 51.4 mmol, 1.00 equiv) in batches. The reaction mixture was allowed to warm up to 30 C and stirred for another 16 h. When the reaction was done, it was quenched by the addition of water (200 mL) and the pH value of the resulting mixture was adjusted to ~l with hydrogen chloride solution (2 N). The mixture was then extracted with ethyl acetate (3 x 100 mL), and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified in a silica gel column eluting with ethyl acetate in petroleum ether (10% to 80% gradient) to afford (4E)-5-(3-bromophenyl)pent-4-enoic acid as yellow oil (13.8 g, 90%). MS: m/z = 253.1 [M-H]
82%	With potassium tert-butylate; In tetrahydrofuran; dimethyl sulfoxide; at 24℃; for 18h;Inert atmosphere;	A 1M solution of potassium tert-butoxide in tetrahydrofuran (80 mL) was added dropwise to <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (17 g, 40 mol) in anhydrous DMSO (20 mL) under nitrogen at 24 C, and the solution was stirred 30 min. before addition of 3-bromobenzaldehyde (4.7 mL, 40 mmol). After several minutes a precipitate was observed and an additional 20 mL of DMSO was added to aid solvation, and the reaction was stirred 18 h. The solution was poured onto water (120 mL) and washed with chloroform. The aqueous layer was acidified with cone. HC1 and extracted with chloroform (3 x 250 mL). The organic phase was concentrated and applied to a 65 i Biotage silica gel column, gradient elution from 15- 65% B (A = Hexanes; B = ethyl acetate) over 2L to give J.1, (E)-5-(3- bromophenyl)pent-4-enoic acid, 8.2 g (82%). XH NMR (300 MHz, CDC13) delta 7.45 (t, J = 1.5 Hz, 1H), 7.30 (dt, J = 7.7, 1.5 Hz, 1H), 7.2-7.16 (m, 1H), 7.12 (t, J = 7.7 Hz, 1H), 6.40-6.32 (m, 1H), 6.23-6.14 (m, 1H), 2.52 (s, 4H). LC (Cond.-Jl): RT = 2.0 min; LRMS: Anal. Calcd. for [M-H]" CiiHuBr02: 252.97; found: 252.98.
71%		To a solution of (3-carboxypropyl)triphenylphosphonium (428 g, 1 mol) in dry DMSO (1 L) was added NaH (60% in oil, 100 g, 2.5 mol) by portions at 0 C. The reaction was stirred at room temperature for 30 min and then 3-bromobenzaldehyde (184 g, 1 mol) was added dropwise. The mixture was stirred at room temperature for an additional 2 h and then poured into water (2 L) and extracted with ethyl acetate (500 mL x 3). The aqueous solution was acidified with conc. HCl and extracted with ethyl acetate (800 mL x 3). The combined organic layer was washed with brine (100 mL x 3). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column (PE / EA = 2 : 1) to give (E)-5-(3-bromophenyl)pent-4-enoic acid (180 g, yield: 71 %) as a pale yellow solid.1H NMR (400 MHz, CDCl3) : 7.48 (s, 1H), 7.33 (d, J = 7.6 Hz, 1H), 7.23 (d, J = 8.0 Hz, 1H), 7.15 (t, J = 8.0 Hz, 1H), 6.39-6.35 (m, 1H), 6.23-6.19 (m, 1H), 2.55-2.53 (m, 4H); ESI-MS (M+1)+: 254.9.

58%		[0311j To a solution of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (12.87 g, 30 mmol, 1.0 equiv) in dry DMSO (50 mL) was added NaH (3 g, 75 mmol, 2.5 equiv) by portions at 0 C. The reaction was stirred at room temperature for 30 mm before 3 -bromobenzaldehyde (5.5 g, 30 mmol, 1.0 equiv) was dropwise added. The mixture was stirred at room temperature for another 2 h and then poured into water (200 mL) and extracted with EA (100 mL). The aqueous solution was acidified with concentrated HC1 and extracted with EA (200 mL x 3). The combined organic layer was washed with brine (100 mL x 3). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column (petroleum ether/EtOAc = 2 : 1) to give (E)-5-(3-bromophenyl)pent-4-enoic acid (4.4 g, yield: 58%) as a yellow oil. ESI-MS (M+1): 254.9. ?H NMR (400 MHz, CDC13) 5: 7.48 (s, 1H), 7.33 (d, J= 7.6 Hz, 1H), 7.23 (d, J= 8.0 Hz, 1H), 7.15 (t, J= 8.0 Hz, 1H), 6.39-6.35 (m, 1H), 6.23-6.19 (m, 1H), 2.55-2.53 (m, 4H).
58%		To a solution of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (12.87 g, 30 mmol, 1.0 equiv) in dry DMSO (50 mL) was added NaH (3 g, 75 mmol, 2.5 equiv) by portions at 0 oC. The reaction was stirred at room temperature for 30 min before 3-bromobenzaldehyde (5.5 g, 30 mmol, 1.0 equiv) was dropwise added. The mixture was stirred at room temperature for another 2 h and then poured into water (200 mL) and extracted with EtOAc (100 mL). The aqueous solution was acidified with concentrated HCl and extracted with EtOAc (200 mL x 3). The combined organic layer was washed with brine (100 mL x 3). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column (petroleum ether/EtOAc = 2 : 1) to give (E)-5-(3-bromophenyl)pent-4-enoic acid (4.4 g, yield: 58%) as a yellow oil. ESI-MS (M+1)+: 254.9. 1H NMR (400 MHz, CDCl3) delta: 7.48 (s, 1H), 7.33 (d, J = 7.6 Hz, 1H), 7.23 (d, J = 8.0 Hz, 1H), 7.15 (t, J = 8.0 Hz, 1H), 6.39-6.35 (m, 1H), 6.23-6.19 (m, 1H), 2.55-2.53 (m, 4H).

Reference： [1]Patent: WO2020/43638,2020,A1 .Location in patent: Paragraph 00163
[2]Patent: WO2012/18325,2012,A1 .Location in patent: Page/Page column 138-139
[3]Patent: WO2015/89327,2015,A1 .Location in patent: Paragraph 0496
[4]Patent: WO2015/89337,2015,A1 .Location in patent: Paragraph 0311
[5]Patent: WO2018/191577,2018,A1 .Location in patent: Page/Page column 126

25
[ 17857-14-6 ]
[ 591-31-1 ]
[ 1226467-43-1 ]

Yield	Reaction Conditions	Operation in experiment
77%		56. 5-(3'-Methoxyphenyl)pent-4-enoic acid (56) To a solution of THF (500 mL) was added <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (18.92 g, 44.1 mmol) and potassium tert-butoxide (10.50 g, 93.6 mmol). The solution was allowed to stir for 1 h at ambient temperature. 3-Methoxybenzaldehyde (5.38 g, 39.5 mmol) was dissolved into THF (10 mL) then added drop-wise to the reaction mixture in anhydrous THF (5 mL), which was allowed to stir for 12 h at ambient temperature. The solution was quenched with 2M HCl (25 mL), and the organic solvent was evaporated under reduced pressure. The aqueous phase was extracted with EtOAc (4*50 mL), washed with brine, dried over Na2SO4, filtered, evaporated under reduced pressure, and purified by flash chromatography with a prepacked 100 g silica gel column [eluents; solvent A, EtOAc, solvent B, hexanes; gradient, 10% A/90% B?12% A/88% B (1 CV), 12% A/88% B?71% A/29% B (8 CV); flow rate, 40 mL/min; monitored at lambdalambda254 and 280 nm]. Pentenoic acid analog 56 (0.879 g, 3.46 mmol, 77% yield) was obtained as a mixture of E and Z isomers and was a yellow solid. 1H NMR (CDCl3, 500 MHz) Reported as E & Z mixture: delta 7.26 (1H, t, J=7.9 Hz), 7.20 (1H, t, J=7.9 Hz), 6.94 (1H, d, J=7.7 Hz), 6.88 (1H, m), 6.85-6.80 (3H, m), 6.77 (1H, ddd, 8.2, 2.6, 1.8 Hz), 6.46 (1H, d, J=11.6 Hz), 6.42 (1H, d, J=15.8 Hz), 6.21 (1H, m), 5.64 (1H, m), 3.813 (3H, s), 3.806 (3H, s), 2.67 (2H, m), 2.54 (4H, m), 2.49 (2H, t, J=7.7 Hz).
74%		4.1.1.43 5-(3'-Methoxyphenyl)pent-4-enoic acid (2)<ce-sup primary_key="ce-sup-332437-none">31,33 To dissolved 3-(carboxypropyl)triphenyl phosphonium bromide (15.92 g, 37.09 mmol) in THF (500 mL) was added potassium tert-butoxide (8.20 g, 73.4 mmol), and the reaction mixture was stirred at room temperature for 1 h. 3-Methoxybenzaldehyde (4.5 mL, 37 mmol) was added, and the reaction mixture was stirred at room temperature for 12 h. The THF was evaporated, and the resulting material was quenched with 2 M HCl (75 mL) and extracted with EtOAc (3 * 50 mL). The combined organic phase was dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude reaction product was purified by flash chromatography using a pre-packed 100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 12% A/88% B (1 CV), 12% A/88% B ? 70% A/30% B (10 CV), 70% A/30% B (2 CV); flow rate: 50 mL/min; monitored at 254 and 280 nm] to afford carboxylic acid 2 (5.63 g, 27.3 mmol, 74%) as a yellow solid. NMR characterization was performed after the next step.

Reference： [1]MedChemComm,2012,vol. 3,p. 720 - 724
[2]Patent: US2012/130129,2012,A1 .Location in patent: Page/Page column 18
[3]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520
[4]Journal of Organic Chemistry,2013,vol. 78,p. 1718 - 1729

26
[ 17857-14-6 ]
[ 6500-64-7 ]

Reference： [1]Patent: US2012/130129,2012,A1
[2]Journal of Organic Chemistry,2013,vol. 78,p. 1718 - 1729
[3]MedChemComm,2012,vol. 3,p. 720 - 724
[4]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520
[5]Patent: WO2019/109188,2019,A1

27
[ 17857-14-6 ]
[ 86-51-1 ]
[ 1378238-71-1 ]

Yield	Reaction Conditions	Operation in experiment
72%		4.1.1.1 5-(2',3'-Dimethoxyphenyl)pent-4-enoic acid (1)<ce-sup primary_key="ce-sup-317336-none">31,33 To dissolved 3-(carboxypropyl)triphenyl phosphonium bromide (13.04 g, 30.39 mmol) in THF (500 mL) was added potassium tert-butoxide (7.43 g, 66.2 mmol), and the reaction mixture was stirred at room temperature for 1 h. 2,3-Dimethoxybenzaldehyde (5.02 g, 30.1 mmol) dissolved in THF (100 mL) was added, and the mixture was stirred at room temperature for 12 h. The THF was removed under reduced pressure, and the resulting material was quenched with 2 M HCl (75 mL) and extracted with EtOAc (3 * 100 mL). The combined organic layers were evaporated under reduced pressure, and the crude reaction product was purified by flash chromatography using a pre-packed 100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 10% A/90% B (1 CV), 10% A/90% B ? 50% A/50% B (10 CV), 50% A/50% B (2 CV); flow rate: 40 mL/min; monitored at 254 and 280 nm] to afford compound 1 (5.39 g, 21.5 mmol, 72%) as a yellow oil. NMR characterization was conducted after the next step.
58%		17. (Z)/(E)-5-(2',3'-Dimethoxyphenyl)pent-4-enoic acid (17) K-OtBu (11.3 g, 101.0 mmol) was added to a well-stirred solution of Wittig salt, <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong>, (21.65 g, 50.43 mmol) in THF (500 mL, anhyd) at rt. The reaction mixture was then cooled to 0 C. and stirred for 15 mins. Solution of 2,3-dimethoxybenzaldehyde (8.42 g, 50.7 mmol) in THF (60 mL, anhyd) was added dropwise to the reaction mixture and the reaction was stirred until the temperature gradually warmed to rt. The reaction was quenched by careful addition of H2O (50 mL) and extracted with Et2O (2200 mL). The aqueous phase was acidified with 2M HCl until the product precipitates making the solution cloudy and then becomes clear again. This acidified aqueous phase was extracted with EtOAc (3100 mL). The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated on a rotavapor. Flash chromatography of the crude using a prepacked 160 g silica column, Eluents; solvent A, EtOAc, solvent B, hexanes; gradient, 20% A/80% B over 3.18 min (1 CV), 10% A/80% B?60% A/40% B over 33.0 min (10 CV), 60% A/40% B over 6.36 min (2 CV); flow rate 50.0 mL/min; monitored at lambdalambda254 and 280 nm afforded the mixture of E/Z-isomers 17 (6.98 g, 29.5 mmol, 58% yield), as a pale yellow liquid.
58%		To a well-stirred solution of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (21.65g, 50.43mmol) in THF (500mL) was added K-OtBu (11.3g, 101mmol). The reaction mixture was then cooled to 0C and stirred for 15min. A solution of aldehyde 3 (8.42g, 50.7mmol) in THF (60mL) was added dropwise, and the reaction mixture was allowed to reach room temperature. The reaction mixture was diluted with H2O (50mL) and extracted with Et2O (2× 200mL). The aqueous phase was acidified with 2 M HCl until the product precipitated making the solution cloudy and then becoming clear again. This acidified aqueous phase was extracted with EtOAc (3× 100mL). The organic extract was washed with brine, dried over Na2SO4, filtered, concentrated under reduced pressure, and subjected to flash chromatography using a prepacked 160 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 20% A/80% B (1 CV), 20% A/80% B? 60% A/40% B (10 CV), 60% A/40% B (2 CV); flow rate: 50mL/min; monitored at 254 and 280 nm] affording a mixture of E/Z-isomers 8 (6.98g, 29.5mmol, 58%) as a pale yellow oil. 1H NMR (E/Z-isomers) (CDCl3, 500MHz): delta 7.03-6.99 (3H, m), 6.85-6.74 (3H, m), 6.76 (1H, d, J=15.9Hz), 6.59 (1H, dt, J=11.5, 1.5Hz), 6.22 (1H, dt, J=15.9, 6.0Hz), 5.70 (1H, dt, J=11.5, 7.5Hz), 3.86 (3H, s), 3.85 (3H, s), 3.78 (3H, s), 3.76 (3H, s), 2.60-2.53 (6H, m), 2.46 (2H, m). 13C NMR (E/Z-isomers) (CDCl3, 125MHz): delta 179.14, 179.12, 153.0, 152.8, 146.9, 146.3, 131.5, 131.4, 130.7, 129.5, 125.7, 125.4, 124.0, 123.6, 121.9, 118.0, 111.3, 111.0, 60.8, 60.6, 55.8, 55.8, 34.0, 33.8, 28.3, 24.0.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520
[2]Patent: US2012/130129,2012,A1 .Location in patent: Page/Page column 9
[3]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 8019 - 8032

28
[ 17857-14-6 ]
[ 54881-49-1 ]
[ 1378238-89-1 ]

Yield	Reaction Conditions	Operation in experiment
98%		42. (E)/(Z) 5-(2'-Chloro-3'-methoxyphenyl)penta-4-en-1-oic acid (42) K-OtBu (6.99 g, 62.3 mmol) was added to a well-stirred solution of (3-carboxypropyl)triphenylphosphonium bromide (13.1 g, 30.5 mmol) in THF (250 mL, anhyd) at rt. The reaction mixture was then cooled to 0 C. and stirred for 15 mins. Solution of 2-Chloro-3-methoxybenzaldehyde (3.44 g, 20.2 mmol) in THF (25 mL, anhyd) was added dropwise to the reaction mixture and the reaction was stirred until the temperature gradually warmed to r.t. The reaction was quenched by careful addition of H2O (50 mL) and extracted with Et2O (2250 mL). The aqueous phase was acidified with 2M HCl until the product precipitates making the solution cloudy and then becomes clear again. This acidified aqueous phase was extracted with EtOAc (3100 mL). The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated on a rotavapor. Flash chromatography of the crude using a prepacked 50 g silica column, Eluents; solvent A, EtOAc, solvent B, hexanes; gradient, 40% A/60% B over 1.39 min (1 CV), 40% A/60% B?80% A/20% B over 16.3 min (10 CV), 60% A/40% B over 3.18 min (2 CV); flow rate 40.0 mL/min; monitored at lambdalambda254 and 280 nm afforded the mixture of E/Z-isomers 42 (4.80 g, 19.9 mmol, 98% yield), as a colorless liquid.
		To a well stirred solution of (3-carboxypropyl)triphenylphosphonium bromide (13.1g, 30.5mmol) in THF (250mL) was added K-OtBu (6.99, 62.3mmol). The reaction mixture was then cooled to 0C and stirred for 15min. A solution of 2-fluoro-3-methoxybenzaldehyde 5 (3.44g, 20.2mmol) in THF (25mL) was added drop wise and the reaction mixture was allowed to warm to room temperature. H2O (50mL) was added and the reaction mixture was extracted with Et2O (2× 250mL). The aqueous phase was acidified with 2 M HCl until the product precipitated making the solution cloudy, and then becoming clear again. The acidified aqueous phase was extracted with EtOAc (3× 100mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, concentrated under reduced pressure affording a crude mixture of the E/Z isomers 9 (4.80g, 19.9mmol, crude yield 98%) as a colorless liquid. The crude product was used in the next step without further purification.

Reference： [1]Patent: US2012/130129,2012,A1 .Location in patent: Page/Page column 15
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 8019 - 8032

29
[ 53055-05-3 ]
[ 17857-14-6 ]
[ 1378238-56-2 ]

Yield	Reaction Conditions	Operation in experiment
58%		1. (Z/E) 5-(3'-Methoxy-2'-nitrophenyl)pent-4-enoic acid (1) To a solution of anhydrous THF (60 mL) under N2 was added <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (2.66 g, 6.21 mmol) and potassium tert-butoxide (1.68 g, 14.9 mmol). The solution was allowed to stir for 1 h at ambient temperature. 3-Methoxy-2-nitrobenzaldehyde (1.07 g, 5.91 mmol) was added dropwise to the reaction mixture in THF (5 mL), which was allowed to stir for 12 h at ambient temperature. The solution was quenched with 2 M HCl (20 mL), and the organic solvent was evaporated under reduced pressure. The aqueous phase was extracted with EtOAc (4*30 mL), washed with brine, dried over Na2SO4, filtered, evaporated under reduced pressure, and purified by flash chromatography with a prepacked 100 g silica gel column [eluents; solvent A, EtOAc, solvent B, hexanes; gradient, 10% A/90% B?2% A/88% B (1 CV), 12% A/88% B?100% A/0% B (13 CV), 100% A/0% B (1.5 CV); flow rate, 40 mL/min; monitored at lambdalambda254 and 280 nm]. Pentenoic acid analog 1 (0.879 g, 3.46 mmol, 58% yield) was obtained as a mixture of E and Z isomers and as a red solid, Rf=0.16 (50:50 hexanes:EtOAc). 1H NMR (CDCl3, 500 MHz) Reported as E & Z mixture: delta 7.38 (1H, t, J=8.1 Hz), 7.34 (1H, t, J=8.2 Hz), 7.12 (1H, dd, J=8.0 Hz, 0.8 Hz), 6.96 (1H, J=8.4 Hz), 6.89 (2H, d, J=8.4 Hz), 6.37 (1H, d, J=11.4 Hz), 6.31 (2H, m), 5.84 (1H, dt, J=11.4 Hz, 7.3 Hz), 3.90 (3H, s), 3.88 (3H, s), 2.54 (4H, m), 2.45 (4H, m). 13C NMR (CDCl3, 125 MHz) Reported as E & Z mixture: delta 178.1, 178.0, 150.76, 150.74, 134.8, 134.3, 130.62, 130.60, 123.6, 123.5, 121.6, 118.0, 111.2, 110.9, 56.41, 56.39, 33.4, 33.1, 28.0, 23.8. HRMS, m/z: observed 252.0868 [M+H]+, (calcd for C12H14NO5+, 252.0866).

Reference： [1]Patent: US2012/130129,2012,A1 .Location in patent: Page/Page column 6
[2]MedChemComm,2012,vol. 3,p. 720 - 724

30
[ 17857-14-6 ]
[ 103438-88-6 ]
[ 1378238-84-6 ]

Yield	Reaction Conditions	Operation in experiment
92%		37. (E)/(Z) 5-(2'-Fluoro-3'-methoxyphenyl)penta-4-en-1-oic acid (37) K-OtBu (8.96 g, 79.9 mmol) was added to a well-stirred solution of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (17.2 g, 40.1 mmol) in THF (250 mL, anhyd) at rt. The reaction mixture was then cooled to 0 C. and stirred for 15 mins. Solution of 2-Fluoro-3-methoxybenzaldehyde (3.08 g, 20.0 mmol) in THF (25 mL, anhyd) was added dropwise to the reaction mixture and the reaction was stirred until the temperature gradually warmed to rt. The reaction was quenched by careful addition of H2O (50 mL) and extracted with Et2O (2250 mL). The aqueous phase was acidified with 2M HCl until the product precipitates making the solution cloudy and then becomes clear again. This acidified aqueous phase was extracted with EtOAc (3100 mL). The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated on a rotavapor. Flash chromatography of the crude using a prepacked 50 g silica column, Eluents; solvent A, EtOAc, solvent B, hexanes; gradient, 20% A/80% B over 1.39 min (1 CV), 20% A/80% B?80% A/20% B over 16.3 min (10 CV), 80% A/20% B over 3.18 min (2 CV); flow rate 40.0 mL/min; monitored at A's 254 and 280 nm afforded the mixture of E/Z-isomers 37 (4.14 g, 18.5 mmol, 92% yield), as a colorless liquid. Anal., Calcd for C12H13FO3: C, 64.28; H, 5.84. Found: C, 64.49; H, 5.84.
		To a well stirred solution of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (17.2g, 40.1mmol) in THF (250mL) was added K-OtBu (8.96g, 79.9mmol). The reaction mixture was then cooled to 0C and stirred for 15min. A solution of 2-fluoro-3-methoxybenzaldehyde (3.08g, 20.0mmol) in THF (25mL) was added dropwise, and the reaction mixture was allowed to warm to room temperature. The reaction mixture was extracted with Et2O (2× 250mL) and the aqueous phase was acidified with 2 M HCl until the product precipitated making the solution cloud and then becoming clear again. The acidified aqueous phase was extracted with EtOAc (3× 100mL). The combined organic extract was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure, affording a mixture of the E/Z isomers 10 (4.14g, 18.5mmol, crude yield 92%) as a colorless liquid. The crude product was used in the next step without purification.

Reference： [1]Patent: US2012/130129,2012,A1 .Location in patent: Page/Page column 13
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 8019 - 8032

31
[ 17857-14-6 ]
[ 2103-57-3 ]
[ 1378238-61-9 ]

Yield	Reaction Conditions	Operation in experiment
64%		7. (Z)/(E)-5-(2',3',4'-Trimethoxyphenyl)pent-4-enoic acid (7) K-OtBu (12.30 g, 109.6 mmol) was added to a well-stirred solution of Wittig salt, <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong>, (24.06 g, 56.05 mmol) in THF (400 mL, anhyd) at rt. The reaction mixture was then cooled to 0 C. and stirred for 15 mins. Solution of 2,3,4-trimethoxybenzaldehyde (9.84 g, 50.15 mmol) in THF (25 mL, anhyd) was added dropwise to the reaction mixture and the reaction was stirred until the temperature gradually warmed to rt. The reaction was quenched by careful addition of H2O (50 mL) and extracted with Et2O (2200 mL). The aqueous phase was acidified with 2M HCl until the product precipitates making the solution cloudy and then becomes clear again. This acidified aqueous phase was extracted with EtOAc (3100 mL). The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. Flash chromatography of the crude using a prepacked 160 g silica column, Eluents; solvent A, EtOAc, solvent B, hexanes; gradient, 20% A/80% B over 3.18 min (1 CV), 20% A/80% B?60% A/40% B over 33.0 min (10 CV), 60% A/40% B over 6.36 min (2 CV); flow rate 50.0 mL/min; monitored at lambdalambda254 and 280 nm afforded the mixture of E/Z-isomers 7 (9.48 g, 35.60 mmol, 64% yield), as a pale yellow liquid.
64%		To a well-stirred solution of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (24.06 g, 56.05 mmol) in THF (400 mL) was added K-OtBu (12.30g, 109.6 mmol). The reaction mixture was then cooled to 0C and stirred for 15min. A solution of aldehyde 1 (9.84g, 50.2mmol) in THF (25mL) was added dropwise and the reaction mixture was stirred and allowed to reach room temperature. The reaction mixture was diluted with H2O (50mL) and extracted with Et2O (2 × 200mL). The aqueous phase was acidified with 2 M HCl until the product precipitated making the solution cloudy and then becoming clear again. The acidified aqueous phase was extracted with EtOAc (3×100mL). The combined organic extract was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by flash chromatography using a prepacked 160g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 20% A/80% B (1CV), 20% A/80% B ? 60% A/40% B (10CV), 60% A/40% B (2 CV); flow rate: 50mL/min; monitored at 254 and 280 nm] afforded the mixture of E/Z-isomers 6 (9.48g, 35.6mmol, 64%) as a pale yellow liquid. 1H NMR (Mixture of E and Z) (CDCl3, 500MHz): delta 7.11 (1H, d, J=8.7Hz, H-6?), 6.94 (1H, d, J=8.6Hz, H-6?), 6.65 (1H, d, J=8.7 Hz, H-5?), 6.65 (1H, d, J=8.6Hz, H-5?), 6.64 (1H, d, J=16.1Hz, H-5), 6.52 (1H, dt, J=11.5, 2 Hz, H-5), 6.11 (1H, m, H-4), 5.63 (1H, dt, J=11.5, 7Hz, H-4), 3.88-3.83 (3× 3H, s, OCH3-2?, -3?, -4?), 3.88-3.83 (3× 3H, s, OCH3-2?, -3?, -4?), 2.59 (2H, m, CH2-2/3), 2.56-2.54 (4H, m, CH2-2, -3), 2.47 (2H, m, CH2-3/2). 13C NMR (CDCl33, 125MHz) delta 178.9, 178.7, 152.9, 152.8, 151.7, 151.1, 142.3, 142.2, 129.5, 127.5, 125.4, 125.2, 124.4, 124.2, 123.9, 120.7, 107.7, 106.9, 61.1, 61.0, 60.95, 60.89, 56.0, 55.9, 34.0, 33.9, 28.3, 23.9.

Reference： [1]Patent: US2012/130129,2012,A1 .Location in patent: Page/Page column 7
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 8019 - 8032

32
[ 17857-14-6 ]
[ 6500-65-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 1.2: 12 h / 20 °C 2.1: hydrogen / palladium 10% on activated carbon / ethanol / 12 h 3.1: methanesulfonic acid; phosphorus pentoxide / 12 h / Inert atmosphere
	Multi-step reaction with 3 steps 1: lithium hexamethyldisilazane 2: hydrogen; platinum on activated charcoal / methanol 3: methanesulfonic acid; phosphorus pentoxide
	Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.25 h / 20 °C 1.2: 8 h / 0 - 20 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h 3.1: phosphorus pentoxide; methanesulfonic acid / 12 h / Inert atmosphere

	Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C 3.1: phosphorus pentoxide; methanesulfonic acid / 12 h / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 1.2: 16 h / 20 °C / Inert atmosphere 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 24 h / 20 °C 3.1: PPA / 2 h / 100 °C

Reference： [1]Current Patent Assignee: BAYLOR UNIVERSITY - US2012/130129, 2012, A1
[2]Kammath, Viju Balachandran; Šolomek, Tomáš; Ngoy, Bokolombe Pitchou; Heger, Dominik; Klán, Petr; Rubina, Marina; Givens, Richard S. [Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1718 - 1729]
[3]Tanpure, Rajendra P.; George, Clinton S.; Sriram, Madhavi; Strecker, Tracy E.; Tidmore, Justin K.; Hamel, Ernest; Charlton-Sevcik, Amanda K.; Chaplin, David J.; Trawick, Mary Lynn; Pinney, Kevin G. [MedChemComm, 2012, vol. 3, # 6, p. 720 - 724]
[4]Herdman, Christine A.; Devkota, Laxman; Lin, Chen-Ming; Niu, Haichan; Strecker, Tracy E.; Lopez, Ramona; Liu, Li; George, Clinton S.; Tanpure, Rajendra P.; Hamel, Ernest; Chaplin, David J.; Mason, Ralph P.; Trawick, Mary Lynn; Pinney, Kevin G. [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7497 - 7520]
[5]Current Patent Assignee: ONTARIO INSTITUTE FOR CANCER RESEARCH - WO2019/109188, 2019, A1

33
[ 17857-14-6 ]
[ 777-93-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / tetrahydrofuran; dichloromethane / 20 h / 0 - 20 °C 2: hydrogen; 50% palladium on charcoal / ethanol / 6 h / 50 °C

Reference： [1]Asano, Masayoshi; Nakamura, Tsuyoshi; Sekiguchi, Yukiko; Mizuno, Yumiko; Yamaguchi, Takahiro; Kuroda, Takeshi; Tamaki, Kazuhiko; Nishi, Takahide [Tetrahedron Asymmetry, 2013, vol. 24, # 8, p. 449 - 456]

34
[ 17857-14-6 ]
[ 613-45-6 ]
[ 851226-32-9 ]

Yield	Reaction Conditions	Operation in experiment
70%		To a solution of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (2.1 g, 4.9 mmol, 1.2 eq.) in tetrahydrofuran (20 ml) was added dropwise a solution of sodium bis(trimethylsilyl)amide (1.0 M in THF, 9.7 ml, 9.7 mmol, 2.4 eq.) at 0 C. The solution was stirred for 30 min, then cooled to -78 C. A solution of 2,4-dimethoxybenzaldehyde (0.73 g, 4.0 mmol, 1 eq.) in tetrahydrofuran (3 ml) was then added dropwise. The reaction was allowed to warm to room temperature overnight. Water and ether were added. The water layer was separated and acidied with 1 M aqueous hydrochloric acid to pH = 1, then extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was chromatographed on silica gel (3:1 ether:hexanes) to give 0.67 g of product (70%) as a white solid.

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1630 - 1636

35
[ 75792-35-7 ]
[ 17857-14-6 ]
5-(2-isopropoxy-3-methoxyphenyl)pent-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%		(3-Carboxypropyl)triphenylphosponium bromide (9.10 g, 21.2 mmol) was dissolved in THF (50 mL) and cooled to 0 C. n-BuLi (24.0 mL, 1.75 M in hexanes) was added to the solution and stirred for 1 h, warmed to ambient temperature and stirred for 15 min, then cooled to 0 C. Isopropyl protected o-vanillin intermediate 50 (2.02 g, 10.4 mmol) was dissolved in THF (5 mL) and was then added to the phosphine ylide solution. The solution was allowed to warm to ambient temperature while stirring for 12 h. The reaction was quenched with aqueous 2M HCl (30 mL) and extracted with EtOAc (4 x 25 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, evaporated under reduced pressure, and purified using flash chromatography with a pre-packed 100 g silica column [solvent A: EtOAc, solvent B: hexanes; gradient: 5%A / 95%B (1 CV), 5%A /95%B ? 52% A / 48%B (7 CV); flow rate, 12 mL/min; monitored at 254 and 280 nm]. The combined E and Z isomers of alkene analogue 51(1.72 g, 6.51 mmol, 63% yield) was obtained as a yellow oil.
		To an ice-cold solution of potassium tert-butoxide (12.13 g, 108.1 mmol) in DMF (154.0 mL), 3-carboxypropyltriphenylphosphonium bromide (19.89 g, 46.34 mmol) was added and the reaction mixture was stirred for 10 min. A DMF (10.0 mL) solution of aldehyde 6 (6.00 g, 30.9 mmol) was added to the generated ylide, and the reaction mixture was stirred at room temperature for 20 h, followed by the addition of deionized (DI) water to obtain a clear solution. DMF and water were removed under reduced pressure and the crude residue was taken up in EtOAc and water to which the aqueous layer was acidified (pH ~ 1-2) with HCl (2 M). The organic layer was separated, and the aqueous layer was washed twice with EtOAc. The combined organic layer was dried over sodium sulfate, filtered [round bottom flask (250.0 mL)], and concentrated under reduced pressure to obtain the crude intermediate alkene (both E and Z) as an oil. The mixture of alkene geometrical isomers was dissolved in CH3OH (61.6 mL) followed by the slow and careful addition of Pd-C (10 wt%, 1.643 g, 1.544 mmol) under nitrogen to avoid the risk of fire. The resultant heterogeneous mixture was stirred under a hydrogen atmosphere (balloon filled with hydrogen) at room temperature for 24 h. Pd/C was filtered by passage through a Celite bed. The filtrate was collected and the solvent was removed under reduced pressure to obtain an oily liquid. Purification by flash chromatography (Biotage Isolera, silica gel column 0-25% EtOAc-hexane) afforded carboxylic acid 7 (7.80 g, 29.3 mmol, 95%) as an oily liquid.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 8019 - 8032
[2]Tetrahedron Letters,2019,vol. 60,p. 397 - 401

36
[ 57260-73-8 ]
[ 17857-14-6 ]
12,12-dimethyl-5,10-dioxo-1,1,1-triphenyl-11-oxa-6,9-diaza-1-phosphoniatridecane bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%		To a well-stirred slurry of (3- carboxypropyl)(triphenyl)phosphonium bromide (2.0 g, 4.6 mmol) in dry DMF (14.7 mL) at room temperature was added solid N,N-carbonyldiimidazole (904 mg, 5.58 mmol). This mixture was allowed to stir at rt for 45 min and N-(2-aminoethyl)(ieri-butoxy)carboxamide (0.809 mL, 5.11 mmol) was added via syringe. The reaction was then allowed to stir for 90 min at rt. The mixture was partitioned between ethyl acetate and saturated sodium bicarbonate (lOOmL each), the layers were separated and the aqueous layer was extracted with ethyl acetate (3x 50mL). The ethyl acetate was discarded and the aqueous layer was extracted with DCM (4x50mL). The DCM solution was dried with anhydrous sodium sulfate and concentrated to give 2.25g (84%) of 12,12-dimethyl-5,10-dioxo-l,l,l-triphenyl-l l-oxa- 6,9-diaza-l-phosphoniatridecane bromide as a thick oil. *H NMR (300 MHz, CDC13) delta ppm 1.38 (s, 9 H) 1.90 - 2.08 (m, 2 H) 2.75 - 2.88 (m, 2 H) 3.28 - 3.46 (m, 4 H) 3.55 - 3.75 (m, 2 H) 5.85 - 6.02 (m, 1 H) 7.66 - 7.94 (m, 15 H) 8.23 - 8.38 (m, 1 H); HPLC Retention Time: 3.36 min. MS (ESI+) for C29H36N2O3P m/z 491.2 (M)+.

Reference： [1]Patent: WO2014/144017,2014,A2 .Location in patent: Paragraph 0351; 0359
[2]Journal of Materials Chemistry B,2018,vol. 6,p. 8137 - 8147

37
[ 5381-20-4 ]
[ 17857-14-6 ]
(E)-5-(benzo[b]thiophen-3-yl)pent-4-enoic acid [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 5484 - 5487

38
[ 56724-03-9 ]
[ 17857-14-6 ]
5-(3'-methoxy-2'-methylphenyl)pent-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		4.1.1.57 5-(3'-Methoxy-2'-methylphenyl)pent-4-enoic acid (3) To dissolved 3-(carboxypropyl)triphenyl phosphonium bromide (6.55 g, 15.3 mmol) in THF was added potassium tert-butoxide (3.30 g, 29.0 mmol), and the reaction mixture was stirred at room temperature for 1 h. <strong>[56724-03-9]<strong>[56724-03-9]3-Methoxy-2-methylbenzaldehyd</strong>e</strong> (2.01 g, 13.4 mmol) dissolved in THF was added to the original reaction mixture, and the reaction mixture was stirred at room temperature for 12 h. The THF was evaporated, and the resulting material was quenched with 2 M HCl (75 mL) and extracted with EtOAc (3 * 100 mL). The combined organic phase was evaporated under reduced pressure and purified by flash chromatography using a pre-packed 100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 12% A/88% B (1 CV), 12% A/88% B ? 75% A/25% B (10 CV), 75% A/25% B (2 CV); flow rate: 40 mL/min; monitored at 254 and 280 nm] to afford carboxylic acid 3 (2.12 g, 9.62 mmol, 69%) as a yellow oil. NMR characterization was performed after the next step.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520

39
[ 722492-70-8 ]
[ 17857-14-6 ]
5-(2'-ethyl-3'-methoxyphenyl)pent-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		4.1.1.63 5-(2'-Ethyl-3'-methoxyphenyl)pent-4-enoic acid (4) To dissolved 3-(carboxypropyl)triphenyl phosphonium bromide (3.56 g, 8.30 mmol) in THF (500 mL) was added potassium tert-butoxide (2.03 g, 18.1 mmol), and the reaction mixture was stirred at room temperature for 1 h. 2-Ethyl-3-methoxybenzaldehyde (1.35 g, 8.22 mmol) dissolved in THF (100 mL) was added to the original reaction mixture and stirred at room temperature for 12 h. The THF was evaporated, and the resulting material was quenched with 2 M HCl (75 mL) and extracted with EtOAc (3 * 100 mL). The combined organic layer was evaporated under reduced pressure and purified by flash chromatography using a pre-packed 100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 7% A/93% B (1 CV), 7% A/93% B ? 60% A/40% B (10 CV), 60% A/40% B (2 CV); flow rate: 50 mL/min; monitored at 254 and 280 nm] to afford carboxylic acid 4 (1.78 g, 7.60 mmol, 92%) as an orange-yellow oil. NMR characterization was performed after the next step.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520

40
[ 17857-14-6 ]
[ 97582-12-2 ]
(E/Z)-5-(3-methoxy-2-propylphenyl)-4-pentenoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%		4.1.1.69 5-(3'-Methoxy-2'-propylphenyl)pent-4-enoic acid (5) To dissolved 3-(carboxypropyl)triphenyl phosphonium bromide (4.43 g, 10.3 mmol) in THF (500 mL) was added potassium tert-butoxide (2.52 g, 22.5 mmol), and the reaction mixture was stirred at room temperature for 1 h. 3-Methoxy-2-propylbenzaldehyde (1.82 g, 10.2 mmol) dissolved in THF (100 mL) was added to the original reaction mixture and stirred at room temperature for 12 h. The THF was evaporated, and the residue was quenched with 2 M HCl (75 mL) and extracted with EtOAc (3 * 100 mL). The combined organic phase was evaporated under reduced pressure and purified by flash chromatography using a pre-packed 100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 7% A/93% B (1 CV), 7% A/93% B ? 60% A/40% B (10 CV), 60% A/40% B (2 CV); flow rate: 50 mL/min; monitored at 254 and 280 nm] to afford compound 5 (2.25 g, 9.06 mmol, 89%) as a yellow oil. NMR characterization was performed after the next step.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520

41
[ 17857-14-6 ]
2-butyl-3-methoxybenzaldehyde [ No CAS ]
5-(2'-butyl-3'-methoxyphenyl)pent-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%		4.1.1.79 5-(2'-Butyl-3'-methoxyphenyl)pent-4-enoic acid (6) A mixture of 3-(carboxypropyl) triphenylphosphonium bromide (4.52 g, 10.6 mmol) and potassium tert-butoxide (2.62 g, 23.2 mmol) in THF (100 mL) was stirred for 1 h at room temperature. 2-Butyl-3-methoxybenzaldehyde (2.03 g, 10.6 mmol) in THF (20 mL) was added dropwise to the reaction mixture and stirred for 12 h at room temperature. The reaction was quenched with 2 M HCl (15 mL), then extracted with EtOAc (3 * 50 mL). The combined organic phase was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The crude reaction product was purified by flash chromatography using a prepacked 100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 7% A/93% B (3 CV), 7% A/3% B ? 60% A/40% B (10 CV), 60% A/40% B (1 CV); flow rate: 40 mL/min; monitored at 254 and 280 nm] to afford carboxylic acid 6 (2.38 g, 9.07 mmol, 86%). NMR characterization was performed after the next step.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520

42
[ 90-96-0 ]
[ 17857-14-6 ]
5,5-bis(4-methoxyphenyl)pent-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%		In an inert atmosphere, NaH (2.0 g, 49.5 mmol) was added in dry DMSO (50 mL). The mixture wasstirred at 70 C for 1 h. The mixture was cooled to 20 C and 4-(bromotriphenylphosphoranyl)-butanoicacid (8.5 g, 19.8 mmol) was added in several portions over 5 min. The red solution was stirred at 20 Cfor 15 min, then a solution of bis(4-methoxyphenyl)methanone (6.0 g, 24.8 mmol) in dry THF (33 mL)was added at such a rate. The mixture was stirred at rt for 19 h, then it was diluted with ice waterand extracted with CH2Cl2. The organic extracts were discarded and the aqueous layer was acidifiedwith 12 N HCl and extracted with CH2Cl2. The organic layer was washed with brine (2 times) anddried over MgSO4. The crude compound was purified by column chromatography to give the desiredproduct (3.1 g, 50% yield).

Reference： [1]Molecules,2016,vol. 21

43
[ 104-53-0 ]
[ 17857-14-6 ]
[ 344359-68-8 ]
(Z)-7-phenylhept-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%		General procedure: The general procedure and characterization of 3 are also presented in ref. 17 of the text: To an ice-cold suspension of 2a (432 mg, 1.01 mmol, 2 equiv) in THF (5 mL) was added NaHMDS (1.0 M in THF, 1.0 mL, 1.0 mmol, 2 equiv). The mixture was stirred at 0 C for 1 h and the resulting reddish-orange mixture was cooled to-95 ~ -90 C (abbreviated as -90 C) (realized by making a slushy mixture of hexane and liquid N2). A solutionof aldehyde 1 (67 mg, 0.50 mmol, 1 equiv) in THF (1.5 mL) was added to the mixture dropwise. After 1 h, the mixture was warmed to 0 C over 2 h before addition of saturated NH4Cl. The resulting mixture was extracted with Et2O three times. The combined extracts were dried over MgSO4 and concentrated to afford a residue, which was purified by chromatography on silica gel (hexane/EtOAc) to give olefin 3 (66 mg, 63%): Z/E 90:10; liquid; Rf 0.13 (hexane/EtOAc 4:1); IR (neat) 2924, 1710, 699 cm-1; 1H NMR (300 MHz, CDCl3) delta 1.5-3.0 (br s, 1 H), 2.24-2.44 (m, 6 H), 2.66 (t, J = 7.5 Hz, 2 H), 5.30-5.42 (m, 1 H), 5.42-5.53 (m, 1 H), 7.14-7.32 (m, 5 H); 13C-APT NMR (75 MHz, CDCl3) delta 22.5 (-), 29.2 (-), 34.0 (-), 35.8 (-), 125.9 (+), 127.9 (+), 128.3 (+), 128.5 (+),130.5 (+), 141.9 (-), 179.8 (-); HRMS (FAB+) calcd for C13H16O2Na [(M+Na)+] 227.1048, found 227.1045.

Reference： [1]Synlett,2019,vol. 30,p. 333 - 337
[2]Organic Letters,2016,vol. 18,p. 504 - 507

44
[ 537013-51-7 ]
[ 17857-14-6 ]
(E)-5-(4-bromo-2,6-difluorophenyl)pent-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.6%		To a RT suspension of (3-carboxypropyl)-triphenylphosphonium bromide (2.91 g, 6.79 mmol) in THF (100 mL) was added dropwiseNaN(TMS)2 (13.57 mL of a 1N solution in THF; 13.57 mmol) over 10 mm under Ar. The mixture was stirred at rt for1.5 h, after which the suspension became dark orange. To this mixture was added <strong>[537013-51-7]4-bromo-2,6-difluorobenzaldehyde</strong> (1.0 g, 4.52 mmol) and the reaction was stirred at rt overnight under Ar, then was quenched with 10% aq. citric acid and water (200 mL) was added. The aqueous phase was extracted with EtOAc (2x100 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo. Theresidue was chromatographed (Si02 80 g; A = Hex, B = EtOAc/1%AcOH; 40 mm gradient from 0% B to 60% B; flow rate = 60 mL/min) to afford the title compound (0.97 g, 3.33 mmol, 73.6% yield) as a pale yellow solid. 1H NMR (500 MHz, CD3OD) oe 7.17 - 7.04 (m, 2H), 6.49 - 6.26 (m, 1H), 6.04 - 5.84 (m, 1H), 2.42 (t, J=6.7 Hz, 1H), 2.40 - 2.34 (m, 1H), 2.29 - 2.24 (m, 1H), 2.21 - 2.14 (m, 1H).

Reference： [1]Patent: WO2016/40225,2016,A1 .Location in patent: Paragraph 00260

45
[ 17857-14-6 ]
[ 146073-06-5 ]
(E)-5-(1-(phenylsulfonyl)-1H-indol-4-yl)pent-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		To a suspension of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (0.92g, 2.2mmol) in THF (12mL), NaHMDS (2.2mL, 4.3mmol) was added dropwise at temperature of-20C and the suspension and further stirred for 20min. The mixture was cooled to-78C and then aldehyde 6 (0.57g, 2.0mmol) was added. After stirred for 18h, the solvent was removed in vacuo and H2O was added. The residue was extracted with diethyl ether and the H2O layer was acidified to pH 2 using HCl (1M). The acidified aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness. The product was purified over silica gel using ethyl acetate: petroleum (1:1) to obtain the alkenoic acid (1.4mmol, 0.48g) as yellow oil. Yield: 68%. 1H NMR (400MHz, Chloroform-d) delta 7.92-7.82 (m, 3H), 7.58 (d, J=3.7Hz, 1H), 7.53-7.46 (m, 1H), 7.40 (t, J=7.8Hz, 2H), 7.32-7.21 (m, 2H), 6.81 (d, J=3.5Hz, 1H), 6.76-6.65 (m, 1H), 6.27 (dt, J=15.9, 6.3Hz, 1H), 2.56 (q, J=5.6, 4.5Hz, 4H).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 663 - 675

46
[ 29421-72-5 ]
[ 17857-14-6 ]
5-(5-methylthiophen-3-yl)pent-4-enoic acid [ No CAS ]
5-(5-methylthiophen-3-yl)pent-4-enoic acid [ No CAS ]

Reference： [1]Organic and biomolecular chemistry,2018,vol. 16,p. 8559 - 8564

47
[ 89922-82-7 ]
[ 17857-14-6 ]
(Z)-7-[(tert-butyldimethylsilyl)oxy]hept-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		To an ice-cold suspension of 4c (10.8 g, 25.2 mmol, 1.5 equiv) in THF (60 mL) and HMPA (15 mL) wasadded NaHMDS (1.0 M in THF, 25.2 mL, 25.2 mmol, 1.5 equiv). The resulting reddish-orange mixture wasstirred at 0 C for 1 h and cooled to -90 C. HMPA (1.5 mL) and a solution of aldehyde 29S7 (3.16 g, 16.8 mmol,1 equiv) in THF (6 mL) were sequentially added to the mixture. After 1 h, the mixture was warmed to 0 C over 2h, and diluted with saturated NH4Cl. The resulting mixture was extracted with EtOAc three times. The combinedextracts were dried over MgSO4, and concentrated to afford a residue, which was purified by chromatography onsilica gel to give olefin 30 (2.69 g, 62%): Z/E 97:3; liquid; Rf 0.18 (hexane/EtOAc 4:1); IR (neat) 2955, 1713, 836, 776 cm-1; 1H NMR (300 MHz, CDCl3) delta 0.05 (s, 6 H), 0.89 (s, 9 H), 2.23-2.48 (m, 6 H), 3.61 (t, J = 6.9 Hz,2 H), 5.38-5.52 (m, 2 H); 13C-APT NMR (75 MHz, CDCl3) delta -5.3 (+), 18.4 (-), 22.6 (-), 26.0 (+), 31.0 (-), 34.2(-), 62.8 (-), 127.7 (+), 129.0 (+), 179.6 (-); HRMS (FAB+) calcd for C13H27O3 [(M+H)+] 259.1729, found259.1727.

Reference： [1]Synlett,2019,vol. 30,p. 338 - 342
[2]Journal of Organic Chemistry,2019,vol. 84,p. 495 - 505

48
[ 17857-14-6 ]
[ 2043-61-0 ]
[ 1379786-10-3 ]

Yield	Reaction Conditions	Operation in experiment
75%		General procedure: Under an atmosphere of argon, the carboxyalkyl triphenyl phosphonium bromide (2.0 equiv) is dissolved in anhydrous THF (0.6 M) The suspension is cooled to 0 C and KOt-Bu (powder or 1 M in THF; 4.0 equiv) is added dropwise. After 30 min of stirring at room temperature, a solution of the aldehyde (1.0 equiv) in anhydrous THF (2 M) is added dropwise at 0 C. The reaction is stirred at room temperature and after the aldehyde is consumed, the mixture is quenched with 1 M aq. HCl solution (20 mL), extracted with Et2O (3 30 mL) and washed with H2O (2 60 mL). The combined organic layers are washed with brine, dried over anhydrous Na2SO4, filtered and the solvent is removed under reduced pressure. The residue is purified on silica gel to yield the title compound.

Reference： [1]Synthesis,2018,vol. 50,p. 3875 - 3885

49
[ 107-75-5 ]
[ 17857-14-6 ]
(Z)-11-hydroxy-7,11-dimethyldodec-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%		General procedure: Under an atmosphere of argon, the carboxyalkyl triphenyl phosphonium bromide (2.0 equiv) is dissolved in anhydrous THF (0.6 M) The suspension is cooled to 0 C and KOt-Bu (powder or 1 M in THF; 4.0 equiv) is added dropwise. After 30 min of stirring at room temperature, a solution of the aldehyde (1.0 equiv) in anhydrous THF (2 M) is added dropwise at 0 C. The reaction is stirred at room temperature and after the aldehyde is consumed, the mixture is quenched with 1 M aq. HCl solution (20 mL), extracted with Et2O (3 30 mL) and washed with H2O (2 60 mL). The combined organic layers are washed with brine, dried over anhydrous Na2SO4, filtered and the solvent is removed under reduced pressure. The residue is purified on silica gel to yield the title compound.

Reference： [1]Synthesis,2018,vol. 50,p. 3875 - 3885

50
[ 104-53-0 ]
[ 17857-14-6 ]
(Z)-7-phenylhept-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		General procedure: Under an atmosphere of argon, the carboxyalkyl triphenyl phosphonium bromide (2.0 equiv) is dissolved in anhydrous THF (0.6 M) The suspension is cooled to 0 C and KOt-Bu (powder or 1 M in THF; 4.0 equiv) is added dropwise. After 30 min of stirring at room temperature, a solution of the aldehyde (1.0 equiv) in anhydrous THF (2 M) is added dropwise at 0 C. The reaction is stirred at room temperature and after the aldehyde is consumed, the mixture is quenched with 1 M aq. HCl solution (20 mL), extracted with Et2O (3 30 mL) and washed with H2O (2 60 mL). The combined organic layers are washed with brine, dried over anhydrous Na2SO4, filtered and the solvent is removed under reduced pressure. The residue is purified on silica gel to yield the title compound. (Z)-7-Phenylhept-4-enoic acid Following general procedure B: 3-phenylpropionaldehyde (402 mg, 3.00 mmol, 1.00 equiv), <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (2.57 g, 6.00 mmol, 2.00 equiv), KOt-Bu (1.30 g, 12.0 mmol, 4.00 equiv), THF (15 mL); the reaction is stirred for 5 h; eluting with n-pentane/EtOAc, 95:5 to 80:20; yield: 590 mg, 2.90 mmol, 96%, yellow liquid.

Reference： [1]Synthesis,2018,vol. 50,p. 3875 - 3885

51
[ 10401-18-0 ]
[ 17857-14-6 ]
5-(2-bromo-3-methoxyphenyl)pent-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%		To dissolved 3-(carboxypropyl)triphenyl phosphonium bromide (5.33 g, 12.4 mmol) in THF (250 mL) was added potassium tert-butoxide (3.08 g, 27.3 mmol), and the reaction mixture was stirred at room temperature for 1 h. 2-Bromo-3-methoxybenzaldehyde 42 (2.67 g, 16.2 mmol) was added, and the reaction mixture was stirred at room temperature for 12 h. The THF was removed under reduced pressure, and the resulting material was quenched and acidified with 2 M HCl (30 mL) and extracted with EtOAc (3*50 mL). The combined organic phase was dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude reaction product was purified by flash chromatography using a pre-packed 100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 12% A/88% B (1 CV), 12% A/88% B?60% A/40% B (10 CV), 60% A/40% B (2 CV); flow rate: 100 mL/min; monitored at 254 and 280 nm] to afford carboxylic acid 43 (1.74 g, 6.10 mmol, 49%) as a white solid. NMR characterization was performed after the next step.

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 5594 - 5615
[2]Patent: US2020/55805,2020,A1 .Location in patent: Paragraph 0064

52
[ 17857-14-6 ]
[ 128495-46-5 ]
(E)-5-(4-fluoro-3-methoxyphenyl)pent-4-enal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%		To a solution of (3-carboxypropyl)triphenylphosphonium bromide (79 g, 186 mmol) in dry DMSO (900 mL) in an ice-water cooling bath at 0 C was added NaH (16.9 g, 422 mmol, 60% in oil) in portions. The cooling bath was removed and the reaction mixture was stirred at 18 C for lh. A solution of <strong>[128495-46-5]4-fluoro-3-methoxybenzaldehyde</strong> (26 g, 169 mmol) in DMSO (100 mL) was added dropwise into the reaction mixture and the reaction mixture continued to stir at 18 C for 5 h. The reaction mixture was poured into H20 (2L). The aqueous phase was extracted with EtOAc (400 mL). The organic layer was separated, and the aqueous solution was treated with a concentrated HC1 solution (36wt%) until pH = 5. The aqueous phase was extracted with EtOAc (700 mL x 2). The combined organic layers were concentrated in vacuo to give crude material. The crude product was purified by silica-gel column chromatography (petroleum ether/EtOAc, grading from 6:1 to 1:1) to give (L)-5-(4-fluoro-3-mcthoxyphcnyl)pcnt-4-cnal as a pale white solid (21.2 g, yield: 56%). 1H NMR (DMSO -d6, 400 MHz) d: 12.18 (br, 1H), 7.35-7.08 (m, 2H), 6.88-6.81 (m, 1H), 6.38-5.57 (m, 2H), 3.81 (s, 3H), 2.48-2.46 (m, 2H), 2.36-2.34 (m, 2H).

Reference： [1]Patent: WO2019/222101,2019,A1 .Location in patent: Page/Page column 203

53
[ 17857-14-6 ]
[ 103438-88-6 ]
(E)-5-(2-fluoro-3-methoxyphenyl)pent-4-enal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		General procedure: To a solution of <strong>[17857-14-6](3-carboxypropyl)triphenylphosphonium bromide</strong> (79 g, 186 mmol) in dry DMSO (900 mL) in an ice-water cooling bath at 0 C was added NaH (16.9 g, 422 mmol, 60% in oil) in portions. The cooling bath was removed and the reaction mixture was stirred at 18 C for lh. A solution of 4-fluoro-3-methoxybenzaldehyde (26 g, 169 mmol) in DMSO (100 mL) was added dropwise into the reaction mixture and the reaction mixture continued to stir at 18 C for 5 h. The reaction mixture was poured into H20 (2L). The aqueous phase was extracted with EtOAc (400 mL). The organic layer was separated, and the aqueous solution was treated with a concentrated HC1 solution (36wt%) until pH = 5. The aqueous phase was extracted with EtOAc (700 mL x 2). The combined organic layers were concentrated in vacuo to give crude material. The crude product was purified by silica-gel column chromatography (petroleum ether/EtOAc, grading from 6:1 to 1:1) to give (L)-5-(4-fluoro-3-mcthoxyphcnyl)pcnt-4-cnal as a pale white solid (21.2 g, yield: 56%). 1H NMR (DMSO -d6, 400 MHz) d: 12.18 (br, 1H), 7.35-7.08 (m, 2H), 6.88-6.81 (m, 1H), 6.38-5.57 (m, 2H), 3.81 (s, 3H), 2.48-2.46 (m, 2H), 2.36-2.34 (m, 2H).

Reference： [1]Patent: WO2019/222101,2019,A1 .Location in patent: Page/Page column 203; 214

54
[ 1071490-91-9 ]
[ 17857-14-6 ]
C₃₆H₄₅N₃O₄P⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 5h;	(3) Add 15mL to a 50mL round bottom flaskDichloromethane,NHS activated (3-carboxypropyl) triphenylphosphine bromide (0.182 g, 0.424 mmol),Intermediate compound C1-2 (0.1g, 0.353mmol)And diisopropylethylamine (0.2 mL, 0.494 mmol),The reaction was carried out at room temperature for 5 hours.After the reaction is over,The organic phase was washed three times with 20 mL of deionized water.Wash 25mL of sodium chloride solution,After drying over anhydrous sodium sulfate, it was spin-dried.It was then purified by silica gel column chromatography (dichloromethane: methanol = 50: 1, v / v).Obtained white solid intermediate C1-3(The structure is shown as compound C1-3 in Fig. 2a) (0.173 g, yield: 80%).

Reference： [1]Patent: CN110407873,2019,A .Location in patent: Paragraph 0024; 0026

55
[ 4248-19-5 ]
[ 17857-14-6 ]
C₂₇H₃₁NO₃P⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃;	Furthermore, Boc-NH2 (1 g, 6.25 mmol), TPP-COOH (0.549 g, 1.28 mmol) and NHS (0.443 g, 3.85 mmol), and EDC·HCl (0.989 g, 5.16 mmol) are dissolved in 50 mL DMF, and EDC·HCl (0.989 g, 5.16 mmol) is added while stirring. The mixture is stirred at room-temperature until the Boc-NH2 is completely reacted via monitoring with thin layer chromatography (TLC). When the reaction is complete, 5 mL deionized water is added and stirred for 30 min to quench the reaction. The solvent is removed in vacuo, and the residue is redissolved in 50 mL DCM and washed with 30 mL saturated salt water. The organic phase is dried by using anhydrous magnesium sulfate. After filtering the solid, the filtrate is condensed to obtain a pale yellow liquid (Boc-TPP, 73% yield).

Reference： [1]Journal of Controlled Release,2020,vol. 322,p. 157 - 169

56
[ 58966-34-0 ]
[ 17857-14-6 ]
C₁₂H₁₃ClO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.5 g	Stage #1: (3-carboxypropyl)(triphenyl)phosphonium bromide With sodium bis-(trimethyl-silyl)amide In tetrahydrofuran at -20℃; for 1h; Stage #2: 5-chloro-2-methylbenzaldehyde In tetrahydrofuran at -20℃; for 4h;	1.1 step 1) 13.56g of 1-carboxypropyltriphenylphosphonium bromide was dissolved in 10mL of tetrahydrofuran, cooled to -20°C with a dry ice bath, slowly dripped with 65mL of sodium amide, the addition was completed, and stirred at -20°C for 1 hour.5g of 5-chloro-2-methylbenzaldehyde was dissolved in 20mL of tetrahydrofuran, added dropwise to the above solution, and the reaction was stirred at -20°C for 4 hours.The reaction solution was slowly poured into 20 mL of ice water, back-extracted with methyl tert-butyl ether to remove impurities,The aqueous phase was then adjusted to pH 2-3 with 1M hydrochloric acid, extracted with 20 mL of ethyl acetate, repeated twice, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. 4.5 g of product 1 were obtained
	With sodium bis-(trimethyl-silyl)amide In tetrahydrofuran at -20℃; for 5h;

Reference： [1]Current Patent Assignee: NANJING AGRICULTURAL UNIVERSITY - CN113831253, 2021, A Location in patent: Paragraph 0049; 0056-0058
[2]Chen, He; Cui, Panpan; Ding, Yuan; Hua, Xiude; Huang, Lianrun; Wang, Minghua [Science of the Total Environment, 2022, vol. 830]

57
[ 105-83-9 ]
[ 17857-14-6 ]
[ 2854359-42-3 ]

Yield	Reaction Conditions	Operation in experiment
76.7%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;	Synthesis of TPP-NH₂ (8). To the DMF solution of (3-carboxypropyl)triphenylphosphonium bromide (22.17 mg, 0.052 mmol) and HATU (19.8 mmol, 0.052 mmol), DIEA (27.2 μL, 0.156 mmol) was added. Then N,N-Bis(3-aminopropyl)methylamine (42 μL, 0.26 mmol) was added to the mixture. The reaction solution was stirred at room temperature for 1 h and purified by semi-preparative RP-HPLC to yield TPP-NH2 (19 mg, 76.7%). HRMS (ESI) m/z: calcd. for C29H40N3OP [M+H]2+ 238.6449, found 238.64470.

Reference： [1]Wu, Chunlei; Li, Yanyan; Cheng, Zhehong; Wang, Pengxin; Ma, Zhilong; Liu, Ke; Cheng, Yulian; Zhou, Yimin; Lin, Xian; Shao, Ximing; Yang, Yong; Li, Hongchang; Fang, Lijing [Chinese Chemical Letters, 2022, vol. 33, # 9, p. 4339 - 4344]

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P378
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[ CAS No. 17857-14-6 ] {[proInfo.proName]}

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[ 17857-14-6 ] Synthesis Path-Upstream 1~2

[ 17857-14-6 ] Synthesis Path-Downstream 1~57

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