[ CAS No. 17814-85-6 ] {[proInfo.proName]}

Name: 17814-85-6|(4-Carboxybutyl)triphenylphosphonium bromide|98%
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Quality Control of [ 17814-85-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 17814-85-6 ]

Product Details of [ 17814-85-6 ]

CAS No. :	17814-85-6	MDL No. :	MFCD00011906
Formula :	C₂₃H₂₄BrO₂P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MLOSJPZSZWUDSK-UHFFFAOYSA-N
M.W :	443.31	Pubchem ID :	161236
Synonyms :

Calculated chemistry of [ 17814-85-6 ]

Physicochemical Properties

Num. heavy atoms :	27
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.17
Num. rotatable bonds :	8
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	120.94
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) :	-4.88 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-1.44
Log Po/w (XLOGP3) :	5.81
Log Po/w (WLOGP) :	1.24
Log Po/w (MLOGP) :	5.34
Log Po/w (SILICOS-IT) :	5.16
Consensus Log Po/w :	3.22

Druglikeness

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

Water Solubility

Log S (ESOL) :	-6.21
Solubility :	0.000271 mg/ml ; 0.000000611 mol/l
Class :	Poorly soluble
Log S (Ali) :	-6.65
Solubility :	0.0000995 mg/ml ; 0.000000224 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-8.49
Solubility :	0.00000144 mg/ml ; 0.0000000032 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	4.45

Safety of [ 17814-85-6 ]

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 [ 17814-85-6 ]

* 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 [ 17814-85-6 ]
Downstream synthetic route of [ 17814-85-6 ]

[ 17814-85-6 ] Synthesis Path-Upstream 1~2

1
[ 2067-33-6 ]
[ 603-35-0 ]
[ 17814-85-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	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.
50%	at 80℃; for 48 h;	5-bromopentanoic acid (5.01 g, 0.03 mol) and triphenylphosphine (2.62 g, 0.01 mol) were added to a 100 mL flask, 50 mL of acetonitrile was added and the mixture was heated to 80 ° C for 48 hours. After the reaction was completed, the solvent was spin dried. The reaction system was introduced into cyclohexane to collect precipitated oily precipitate and vacuum-dried product in a yield of 50percent.

Reference： [1] Journal of Organic Chemistry, 1999, vol. 64, # 9, p. 3196 - 3206
[2] Canadian Journal of Chemistry, 2003, vol. 81, # 6, p. 697 - 704
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579
[4] Journal of Organic Chemistry, 1987, vol. 52, # 20, p. 4449 - 4453
[5] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6353 - 6363
[6] Patent: CN104844650, 2017, B, . Location in patent: Paragraph 0143; 0144; 0145
[7] Journal of the American Chemical Society, 1969, vol. 91, p. 4933 - 4934
[8] Tetrahedron, 1993, vol. 49, # 46, p. 10501 - 10510
[9] Journal of Medicinal Chemistry, 1985, vol. 28, # 3, p. 287 - 294
[10] Tetrahedron Letters, 1996, vol. 37, # 9, p. 1393 - 1396
[11] Bioscience, Biotechnology and Biochemistry, 2001, vol. 65, # 9, p. 2065 - 2069
[12] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 22, p. 6467 - 6472
[13] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1905 - 1916
[14] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1718 - 1729
[15] Applied Catalysis A: General, 2014, vol. 470, p. 183 - 188
[16] Organic Letters, 2016, vol. 18, # 3, p. 504 - 507
[17] Organic Letters, 2017, vol. 19, # 18, p. 4940 - 4943
[18] Patent: CN104513186, 2016, B, . Location in patent: Paragraph 0126 - 0128
[19] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 275 - 284

2
[ 542-28-9 ]
[ 6399-81-1 ]
[ 17814-85-6 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1967, vol. 709, p. 105 - 112

[ 17814-85-6 ] Synthesis Path-Downstream 1~29

1
[ 2067-33-6 ]
[ 603-35-0 ]
[ 17814-85-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	In acetonitrile at 80℃; for 24h;
92%	In acetonitrile for 24h; Heating;
88%	In toluene for 48h; Inert atmosphere; Reflux;	3.2.4. General procedure for the synthesis of phosphonium salts (5) 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.

65%	In 5,5-dimethyl-1,3-cyclohexadiene for 2h; Reflux;	4.4.1. (E)-6-(4-Methoxyphenyl)hex-5-enoic acid (16) In a 250 mL flask equipped with a refrigerant containing 10.0 g of 5-bromovaleric acid 15 (1 eq, 55.2 mmol), 16.0 g of triphenylphosphine (1.1 eq., 61.0 mmol) and 150 mL of xylene were added. The mixture was heated at reflux for 2 h with stirring. After cooling them ixture to room temperature, the white precipitate formed was filtered on sintered glass and washed with acetone. After drying,15.92 g of (4-carboxybutyl)triphenylphosphonium bromide were recovered as a white solid with 65% yield.
56%	In acetonitrile for 24h; Heating;
50%	In acetonitrile at 80℃;
50%	In acetonitrile at 80℃; for 48h;	37 Example 37 A quaternary phosphonium salt of the following formula was prepared 5-bromopentanoic acid (5.01 g, 0.03 mol) and triphenylphosphine (2.62 g, 0.01 mol) were added to a 100 mL flask, 50 mL of acetonitrile was added and the mixture was heated to 80 ° C for 48 hours. After the reaction was completed, the solvent was spin dried. The reaction system was introduced into cyclohexane to collect precipitated oily precipitate and vacuum-dried product in a yield of 50%.
	In acetonitrile for 18h; Heating;
	In acetonitrile Heating;
	at 80℃; for 12h;
	In acetonitrile Reflux;
7.42 kg	In toluene for 6h; Reflux; Large scale;
	In acetonitrile Reflux;
	In toluene for 24h; Reflux;	Synthesis of phosphonium-based ionic liquids 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 36h; Schlenk technique; Inert atmosphere; Reflux;
	In acetonitrile for 36h; Schlenk technique; Reflux; Inert atmosphere;
	In toluene for 0.25h; Reflux;	α-1 Preparation of upper side chain: 300g of 5-bromovaleric acid and 420g of triphenylphosphine were added into a 3000ml three-necked flask and 3000ml of tolueneHeat to reflux with stirring for 15 minutes, cool and filter. The filtrate was concentrated to remove toluene. Then add 2000ml of tetrahydrofuran, heated to reflux with stirring, cooled and filtered. The resulting white solid was evacuated in vacuo to yield the upper side chain of the product of reaction al, Mp: 202-206.
	In acetonitrile for 15h; Reflux;	4 4.1.3. Synthesis of compounds 1c-f 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.
	In acetonitrile for 24h; Reflux;	1.4 4. The modification steps of triphenylphosphine are as follows: 5-Bromopentanoic acid (3.1 g, 17.1 mmol) and triphenylphosphine (PPh3, 4.24 g, 16.1 mmol) were added to 40 mL of acetonitrile and heated to reflux for 24 h. The crude product precipitated by freezing filtration, After washing with ethyl acetate for 3 times, a white powder product, PPh3Br-(CH2)4-COOH (abbreviated as TPP), was obtained.
	at 85℃; for 12h;

Reference： [1]De Los Angeles Rey, Maria; Martinez-Perez, Jose Antonio; Fernandez-Gacio, Ana; Halkes, Koen; Fall, Yagamare; Granja, Juan; Mourino, Antonio [Journal of Organic Chemistry, 1999, vol. 64, # 9, p. 3196 - 3206]
[2]Henry-Riyad, Huda; Tidwell, Thomas T. [Canadian Journal of Chemistry, 2003, vol. 81, # 6, p. 697 - 704]
[3]Location in patent: experimental part Wube, Abraham A.; Hüfner, Antje; Thomaschitz, Christina; Blunder, Martina; Kollroser, Manfred; Bauer, Rudolf; Bucar, Franz [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579]
[4]Hamri, Salha; Jouha, Jabrane; Oumessaoud, Asmaa; Pujol; Khouili, Mostafa; Guillaumet, Gérald [Tetrahedron, 2021, vol. 77]
[5]Bergman, Nils-Ake; Jansson, Marie; Chiang, Yvonne; Kresge, A. Jerry; Yin, Ya [Journal of Organic Chemistry, 1987, vol. 52, # 20, p. 4449 - 4453]
[6]Ye, Yaqing; Zhang, Tao; Yuan, Huiqing; Li, Defeng; Lou, Hongxiang; Fan, Peihong [Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6353 - 6363]
[7]Current Patent Assignee: CHONGQING UNIVERSITY OF TECHNOLOGY - CN104844650, 2017, B Location in patent: Paragraph 0143; 0144; 0145
[8]Plattner,J.J. et al. [Journal of the American Chemical Society, 1969, vol. 91, p. 4933 - 4934] Nagumo, Shinji; Matsukuma, Aki; Suemune, Hiroshi; Sakai, Kiyoshi [Tetrahedron, 1993, vol. 49, # 46, p. 10501 - 10510]
[9]Kato, Kaneyoshi; Ohkawa, Shigenori; Terao, Shinji; Terashita, Zen-ichi; Nishikawa, Kohei [Journal of Medicinal Chemistry, 1985, vol. 28, # 3, p. 287 - 294]
[10]Provent, Christophe; Chautemps, Pierre; Gellon, Gisele; Pierre, Jean-Louis [Tetrahedron Letters, 1996, vol. 37, # 9, p. 1393 - 1396]
[11]Takagi, Miho; Takikawa, Hirosato; Mori, Kenji [Bioscience, Biotechnology and Biochemistry, 2001, vol. 65, # 9, p. 2065 - 2069]
[12]Location in patent: experimental part Zamponi, Gerald W.; Feng, Zhong-Ping; Zhang, Lingyun; Pajouhesh, Hossein; Ding, Yanbing; Belardetti, Francesco; Pajouhesh, Hassan; Dolphin, David; Mitscher, Lester A.; Snutch, Terrance P. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 22, p. 6467 - 6472]
[13]Henschke, Julian P.; Liu, Yuanlian; Huang, Xiaohong; Chen, Yungfa; Meng, Dechao; Xia, Lizhen; Wei, Xiuqiong; Xie, Aiping; Li, Danhong; Huang, Qiang; Sun, Ting; Wang, Juan; Gu, Xuebin; Huang, Xinyan; Wang, Longhu; Xiao, Jun; Qiu, Shenhai [Organic Process Research and Development, 2012, vol. 16, # 12, p. 1905 - 1916]
[14]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]
[15]Dai, Wei-Li; Jin, Bi; Luo, Sheng-Lian; Luo, Xu-Biao; Tu, Xin-Man; Au, Chak-Tong [Applied Catalysis A: General, 2014, vol. 470, p. 183 - 188]
[16]Guo, Ruizhi; Huang, Jiachen; Huang, Haiyan; Zhao, Xiaodan [Organic Letters, 2016, vol. 18, # 3, p. 504 - 507]
[17]Zhu, Zechen; Luo, Jie; Zhao, Xiaodan [Organic Letters, 2017, vol. 19, # 18, p. 4940 - 4943]
[18]Current Patent Assignee: NINGBO SECOND HORMONE FACTORY - CN104513186, 2016, B Location in patent: Paragraph 0126 - 0128
[19]Xu, Biao; Yu, Zhimei; Xiang, Sichuan; Li, Yunshan; Zhang, Shao-Lin; He, Yun [European Journal of Medicinal Chemistry, 2018, vol. 155, p. 275 - 284]
[20]Current Patent Assignee: SHANGHAI JIAO TONG UNIVERSITY - CN105833289, 2019, B Location in patent: Paragraph 0046; 0062-0063
[21]Chen, Chih-Wei; Pavlova, Julia A.; Lukianov, Dmitrii A.; Tereshchenkov, Andrey G.; Makarov, Gennady I.; Khairullina, Zimfira Z.; Tashlitsky, Vadim N.; Paleskava, Alena; Konevega, Andrey L.; Bogdanov, Alexey A.; Osterman, Ilya A.; Sumbatyan, Natalia V.; Polikanov, Yury S. [Antibiotics, 2021, vol. 10, # 4]

2
[ 6221-04-1 ]
[ 17814-85-6 ]
(E)-6-[5-((E)-5-Carboxy-pent-1-enyl)-pyridin-3-yl]-hex-5-enoic acid [ No CAS ]
[ 791-28-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 50℃;

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
[ 17814-85-6 ]
[ 71140-70-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium hydroxide for 4h; Heating;

Reference： [1]Even, L.; Florentin, D.; Marquet, A. [Bulletin de la Societe Chimique de France, 1990, # 6, p. 758 - 768]

4
[ 25714-71-0 ]
[ 17814-85-6 ]
[ 109997-30-0 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; dimethyl sulfoxide 1.) hexane, RT, 15 min, 2.) hexane, overnight; Yield given. Multistep reaction;

Reference： [1]Bergman, Nils-Ake; Jansson, Marie; Chiang, Yvonne; Kresge, A. Jerry; Yin, Ya [Journal of Organic Chemistry, 1987, vol. 52, # 20, p. 4449 - 4453]

5
[ 626-19-7 ]
[ 17814-85-6 ]
[ CAS Unavailable ]
[ 71140-70-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1.) DMSO, room t., 2 h; 2.) reflux; Yield given. Multistep reaction;

Reference： [1]Provent, Christophe; Chautemps, Pierre; Gellon, Gisele; Pierre, Jean-Louis [Tetrahedron Letters, 1996, vol. 37, # 9, p. 1393 - 1396]

6
[ 90560-22-8 ]
[ 17814-85-6 ]
[ 71140-70-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1.) DMSO, 2 h, room t.; 2.) reflux; Yield given. Multistep reaction;

Reference： [1]Provent, Christophe; Chautemps, Pierre; Gellon, Gisele; Pierre, Jean-Louis [Tetrahedron Letters, 1996, vol. 37, # 9, p. 1393 - 1396]

7
[ 113293-70-2 ]
[ 17814-85-6 ]
(E)-6-(2,6-Dichloro-pyridin-4-yl)-hex-5-enoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3569 - 3584

8
[ 17814-85-6 ]
[ 95715-87-0 ]
[ 342029-00-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With lithium hexamethyldisilazane In tetrahydrofuran at 15 - 20℃; for 1h;

Reference： [1]Murray, Peter J; Kranz, Michael; Ladlow, Mark; Taylor, Stephen; Berst, Frederic; Holmes, Andrew B; Keavey, Kenneth N; Jaxa-Chamiec, Albert; Seale, Peter W; Stead, Paul; Upton, Richard J; Croft, Simon L; Clegg, William; Elsegood, Mark R.J [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 6, p. 773 - 776]

9
[ 17814-85-6 ]
[ 227940-70-7 ]
[ 454695-23-9 ]

Reference： [1]Chemical Communications,2002,p. 673 - 675
[2]Chemistry - A European Journal,2002,vol. 8,p. 4767 - 4780

10
[ 17814-85-6 ]
[ 551-11-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 1753 - 1760
[2]Synlett,1997,vol. 1997,p. 734 - 736

11
[ 17814-85-6 ]
[ 2867-63-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: NaH / dimethylsulfoxide / 1 h / 20 °C 1.2: 64 percent / dimethylsulfoxide / 4 h / 20 °C 2.1: DCC; DMAP / CH₂Cl₂ / 2 h / 20 °C 2.2: CH₂Cl₂ / 3 h 3.1: 41 percent / tetraethylammonium perchlorate / dimethylformamide / 60 °C / Electrochemical reaction

Reference： [1]Ozaki; Yoshinaga; Matsui; Adachi [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2503 - 2505]

12
[ 17814-85-6 ]
[ 27976-27-8 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3569 - 3584

13
[ 17814-85-6 ]
[ 5581-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, 25 deg C, 1 h, 2.) 25 deg C, 2 h 2: 95 percent / H₂ / 5percent Pd/C / ethyl acetate / 1 h / 25 °C / 1551.4 Torr
	Multi-step reaction with 2 steps 1: lithium hexamethyldisilazane / N,N-dimethyl-formamide; tetrahydrofuran / 3.5 h / 90 °C 2: platinum(IV) oxide; hydrogen / tetrahydrofuran / 1 h / 20 °C

Reference： [1]Gapinski, D. Mark; Mallett, Barbara E.; Froelich, Larry L.; Jackson, William T. [Journal of Medicinal Chemistry, 1990, vol. 33, # 10, p. 2807 - 2813]
[2]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2017/88546, 2017, A1

14
[ 502-72-7 ]
[ 17814-85-6 ]
[ 1011461-45-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: (4-carboxy-n-butyl)-triphenylphosphonium bromide With 1,1,1,3,3,3-hexamethyldisilazane potassium In tetrahydrofuran at 20℃; for 0.5h; Stage #2: cyclopentadecanone In tetrahydrofuran at 20℃;	1; 2 General procedure (A) for the Wittig reaction for the synthesis of compounds 3-6. General procedure: To an ice- cold solution of (3-carboxypropyl) triphenylphosphonium or (4- carboxybutyl)triphenylphosphonium bromide (2 mmol) in THF (6 mL), potassium bis(trimethylsilyl) amide (4 mmol) was added and the mixture was stirred for 30 minutes at rt. Then a solution of cyclododecanone (1) or cyclopentadecanone (2) (1 mmol) in THF (7 mL) was added dropwise and the reaction was stirred at rt overnight. The solvent was removed in vacuo and the mixture was diluted with water and washed with Et2O. The mixture was then acidified to pH 2 and extracted with DCM, dried over Na2SO4 and evaporated to dryness. Pure unsaturated acids were obtained after flash column chromatography.
75%	Stage #1: (4-carboxy-n-butyl)-triphenylphosphonium bromide With 1,1,1,3,3,3-hexamethyldisilazane potassium In tetrahydrofuran at 20℃; for 0.25h; Stage #2: cyclopentadecanone In tetrahydrofuran at 20℃; for 12h; Further stages.;

Reference： [1]Current Patent Assignee: QUADREL - WO2022/63790, 2022, A1 Location in patent: Page/Page column 19-21; 28; 29
[2]Calogeropoulou, Theodora; Angelou, Panagiotis; Detsi, Anastasia; Fragiadaki, Irene; Scoulica, Effie [Journal of Medicinal Chemistry, 2008, vol. 51, # 4, p. 897 - 908]

15
[ 33892-75-0 ]
[ 17814-85-6 ]
(1E)-5-(5-methoxy-3,4-dihydro-2H-naphthalen-1-ylidene)pentanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 30℃; for 1h; Stage #2: 5-Methoxy-1-tetralone In tetrahydrofuran at 20 - 30℃; Stage #3: With water; ammonium chloride In tetrahydrofuran at 0℃;	7 Reference Example 7 5-(5-methoxy-3,4-dihydronaphthalen-1(2H)ylidene)pentanoic acid To an anhydrous tetrahydrofuran (200 ml) solution of (4-carboxybutyl)triphenylphosphonium bromide (25.0 g), potassium t-butoxide (12.7 g) was added, followed by stirring at 30§C for 1 hour. To the reaction mixture, a tetrahydrofuran (20 ml) solution of 5-methoxy-1-tetralone (5.0 g) was added, followed by stirring at room temperature overnight. The reaction mixture was added to a mixture of saturated aqueous ammonium chloride solution and ice, followed by extracting with ethyl acetate. The extract was concentrated to thereby obtain the crude title compound having the following physical data. The obtained compound was used without purification in the subsequent reaction. TLC: Rf 0.34 (hexane: ethyl acetate = 2: 1).

Reference： [1]Current Patent Assignee: ONO PHARMACEUTICAL CO LTD - EP1354879, 2003, A1 Location in patent: Page/Page column 46

16
[ 124-19-6 ]
[ 17814-85-6 ]
[ 5684-70-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: nonan-1-al In tetrahydrofuran at 20℃; for 3h; stereoselective reaction;	3.2.5. General procedure for the synthesis of unsaturated carboxylic acids (6) 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).
64%	Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h; Stage #2: nonan-1-al In tetrahydrofuran at -90 - 0℃; for 3h;	General procedure represented by the synthesis of (Z)-7-phenylhept-4-enoic acid (3) 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%):

Reference： [1]Location in patent: experimental part Wube, Abraham A.; Hüfner, Antje; Thomaschitz, Christina; Blunder, Martina; Kollroser, Manfred; Bauer, Rudolf; Bucar, Franz [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579]
[2]Suganuma, Yuta; Kobayashi, Yuichi [Synlett, 2019, vol. 30, # 3, p. 333 - 337]

17
[ 17814-85-6 ]
[ 155206-00-1 ]

Reference： [1]Patent: WO2011/46569,2011,A1
[2]Patent: KR2017/25682,2017,A

18
[ 856240-62-5 ]
[ 17814-85-6 ]
[ 75-04-7 ]
[ 155206-00-1 ]

Yield	Reaction Conditions	Operation in experiment
		Into a 3 liter 4 necked round bottom flask fitted with a mechanical stirrer and a reflux condenser was charged THF (275 ml), 4-carboxybutyl triphenylphosphonium bromide (90gm) at temperature 25 to 30C. Cooled the reaction mass to -8C to -12C and added potassium tert-butoxide solution (400 ml) (1 molar solution in THF). Charged Example 5 product (15 gm in 75 ml THF) at 5C to 10C and maintained the reaction mass for 2 hours at same temperature. After completion of the reaction charged DM water (300 ml) at 5C to 10C and washed the reaction mass with ether (3 x300 ml). Separated the aqueous layer and adjusted pH to 3 with 20% citric acid solution (70 g of citric acid, water to make 350 ml). Extracted the product with ethyl acetate (3 x300 ml) and removed the solvent by distillation under vacuum at temperature 35C to 45 C. Charged acetone (600 ml) to the obtained residue and filtered the precipitated product and washed with acetone (150 ml). Combined the acetone layer and evaporated under vacuum at temperature below 45C to obtain a residue. To the resultant residue charged dimethyl formamide (150 ml) and sodium carbonate (30 gms). Heated the solution to 25C to 30C and charged methyl iodide (40 ml) and stirred for 12 hours. After completion of the reaction the solvent was removed from the solution under vacuum at 40 C to 45C and charged DM water (300 ml) and extracted the product with ethyl acetate (2x300 ml). Separated the organic layer and washed with 10% citric acid solution (450 ml) (45 g of citric acid, water to make 450 ml). Separated the organic layer and removed the solvent under vacuum at 40 C to 45C to yield the bimatoprost methyl ester as residue. To the residue added 70 % aqueous ethylamine solution (500 ml) at temperature 25C to 30C and stirred for 48 hours at same temperature. After completion of the reaction, concentrated the reaction solution to half of the volume by distillation under vacuum at 40 C to 45C. Charged DM water and adjusted the pH of the reaction mass to 3 to 5 with 30% sodium bisulphate solution (125 ml) (37.5 g of sodium bisulphate, water to make 125 ml) and extracted the product with ethyl acetate (2 125 ml). Separated the organic layer and washed with 10% sodium chloride solution (125 ml). The organic layer was removed by distillation from the reaction mass under vacuum at temperature 35C to 45C to yield title compound as residue. Charged methyl, tertiary butyl ether (125 ml) at temperature 25C to 30C and stirred for 60 minutes. Filtered the precipitated product and washed with chilled methyl tertiary butyl ether (25 ml). The wet product was dried at 35C to 40C under reduced pressure to provide the title compound.Yield: 1 1.5 gms.HPLC purity (chiral): 97.00%Formula A: 2.80%Formula B: 0.20%.Formula C: Not detected

Reference： [1]Patent: WO2012/11128,2012,A1 .Location in patent: Page/Page column 21-22

19
[ 1576-87-0 ]
[ 17814-85-6 ]
[ 229493-98-5 ]

Yield	Reaction Conditions	Operation in experiment
32%	Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With phenyllithium; lithium bromide In tetrahydrofuran; dibutyl ether at -75 - 25℃; Stage #2: trans-2-pentenal In tetrahydrofuran; dibutyl ether at -75 - 25℃; for 1.5h;	2.A (5E, 7E)-5, 7-undecandienoic acid 6. LiBr (1.5 M, 56 mL, 84 mmol) was added to a solution of (4-carboxybutyl)triphenylphosphonium bromide 5 (11.08 g, 25 mmol) in THF (45 mL) and cooled to -75°C. While stirring, PhLi (1.8 M in dibutyl ether, 31 mL, 55 mmol) was added dropwise, keeping the temperature of the reaction mixture between -75°C and -70°C. The cooling bath was removed and the reaction mixture was gradually warmed over 30 min to 25°C. The solution was then cooled to -75°C and (2E)-2-pentenal (2.103 g, 25 mmol) was added via syringe. The reaction mixture was stirred for 5 min at -75°C and PhLi (15 mL, 27 mmol) was added over a period of 30 min. The reaction mixture was then stirred for 30 min at -75°C, warmed to 25°C for 30 min, and then cooled again to -75°C. Hydrogen chloride (1M solution in Et20, 28 mL, 28 mmol) was added. After 5 min, t-BuOK (3.36 g, 30 mmol) was added. The reaction mixture was allowed to warm to 25°C, stirred for 1 h, and poured into ice cold water (90 mL). The reaction mixture was concentrated twice by rotary evaporation. Unreacted aldehyde was extracted with Et20. The aqueous layer was acidified to pH=l with 20% HC1, the product was extracted with Et20, dried (MgSC^), and purified in a Si02 column (Hex:EtOAc: AcOH=8:2:0.05). Yield 1.342 g (32%). XH-NMR (CDC13): LOO t (3H, CH3); 1.70 m (2H, CH2); 2.05-2.15 m (4H, 2CH2); 2.36 t (2H, CH2); 5.48-5.57 m (1H, CH); 5.60-5.67 m (1H, CH); 5.96-6.06 m (2H, 2CH). MS(ES, Neg); 166.9 [M-l] ~; 395.6 [2M +AcOH-l]~.

Reference： [1]Current Patent Assignee: ARROWHEAD RESEARCH CORP - WO2012/173784, 2012, A1 Location in patent: Page/Page column 23-24

20
[ 51388-75-1 ]
[ 17814-85-6 ]
[ 551-11-1 ]

Yield	Reaction Conditions	Operation in experiment
152 mg		4-Carboxybutyl)(triphenyl)phosphonium bromide 29 (de los Angeles Rey, M. et al., J. Org. Chem. 64, 3196-3206 (1999) Note: Material prepared as described in this reference, but using toluene in place of benzene and pentane in place of hexane during the washing of the product) (2.00 g, 4.52 mmol), which corresponds to compound (VIII) described above, was added to a flame dried schlenk flask, under N2, and anhydrous THF (16.0 ml) added. The resulting suspension was cooled to 0 C. KOt-Bu (1.01 g, 9.03 mmol) was added in one portion and the resulting orange mixture stirred at 0 C for 40 min. A solution of crude triol 28 (203 mg, 0.75 mmol) in anhydrous THF (4.0 ml) was added dropwise via syringe. After complete addition the mixture was stirred at r.t. for 1 h. The reaction was quenched with H20 (25 ml) and washed with Et20 (2 x 25 ml) to remove triphenylphosphine oxide. The aqueous phase was made acidic with 1 M HCI (~10 ml) and extracted with CH2CI2 (5 x 25 ml). The combined organic phases were dried (MgS04), filtered, and concentrated to give the crude material. This was triturated with EtOAc/heptane and the solids filtered and washed with EtOAc (4 x 5 ml). The filtrate was concentrated under vacuum and purified by column chromatography on silica, eluting with EtOAc/petrol/AcOH (60:35:5) to give PGF2a. This was dissolved in CH2CI2 and washed with H20 (5 ml). The organic phase was then dried (MgS04), filtered, and concentrated to give PGF2a (152 mg, 57% over 2 steps) as a clear, colourless oil. The H NMR data was consistent with that reported by Mulzer (Sheddan, N. A. et al., Org. Lett. 8, 3101-3104 (2006)). The 13C NMR data was in excellent agreement with that reported by Parve (Parve, O. et al., Bioorg. Med. Chem. Lett. 9, 1853-1858 (1999)). The IR and optical rotation data are in agreement with that reported by Mulzer (Sheddan, N. A. et al., Org. Lett. 8, 3101-3104 (2006)) and Corey (Corey, E. et ai, J. Am. Chem. Soc. 92, 397-398 (1970)). Rf = 0.24 (EtOAc:40/60 petroleum ether:AcOH, 60:35:5) vmax (neatVcm-1 3339, 2961, 2930, 2857, 2490, 1705, 1457, 1380, 1245, 1118, 1086, 1047, 970, 910, 878, 731 *H NMR (400 MHz; CDCfe) deltaEta = 0.89 (3 H, t, J = 6.8 Hz, CH3), 1.24-1.41 (6 H, m, 3 x CH2), 1.43-1.54 (2 H, m,), 1.54-1.63 (1 H, m), 1.63-1.73 (2 H, m), 1.76 (1 H, m), 2.07-2.28 (5 H, m), 2.28-2.39 (3 H, m), 3.96 (1 H, m, CAOH), 4.11 (1 H, q, J = 6.8 Hz, CAOH), 4.18 (1 H, m, CAOH), 4.35-5.20 (1 H, br. s, C02H), 5.32-5.41 (1 H, m, =CH), 5.41-5.50 (1 H, m, =CH), 5.50 (1 H, dd, J = 15.4, 8.4 Hz, =CH), 5.58 (1 H, dd, J = 15.4, 6.6 Hz, =CH) 13C NMR (125 MHz; CDCI3) 5C = 14.0 (CH3), 22.6 (CH2), 24.5 (CH2), 25.2 (CH2), 25.2 (CH2), 26.3 (CH2), 31.7 (CH2), 33.1 (CH2), 36.9 (CH2), 42.7 (CH2), 50.0 (CH), 55.2 (CH), 72.3 (ACOH), 73.2 (ACOH), 77.4 (ACOH), 129.2 (=CH), 129.5 (=CH), 132.8 (=CH), 135.1 (=CH), 177.5 (C=0) HRMS (ESI) calcd for Q^OsNa [MNa+] 377.2298, found 377.2303 [a]D22 -23.5 (c. 1.0, THF) (lit.,49 [a]D20 -24.9 (c. 0.57, THF)) (lit.,51 [a]D25 -23.8 (synthetic material) (c. 1.0, THF)) (lit.,51 [a]D25 -23.5 (natural material) (c. 1.0, THF))
152 mg		5F. (Z)-7-(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(E,3S)-3-hydroxy-1-octenyl]cyclopentyl-5-heptenoic acid, PGF2alpha (1) (4-Carboxybutyl)(triphenyl)phosphonium bromide 29 (de los Angeles Rey, M. et al., J. Org. Chem. 64, 3196-3206 (1999) Note: Material prepared as described in this reference, but using toluene in place of benzene and pentane in place of hexane during the washing of the product) (2.00 g, 4.52 mmol), which corresponds to compound (VIII) described above, was added to a flame dried schlenk flask, under N2, and anhydrous THF (16.0 ml) added. The resulting suspension was cooled to 0 C. KOt-Bu (1.01 g, 9.03 mmol) was added in one portion and the resulting orange mixture stirred at 0 C. for 40 min. A solution of crude triol 28 (203 mg, 0.75 mmol) in anhydrous THF (4.0 ml) was added dropwise via syringe. After complete addition the mixture was stirred at r.t. for 1 h. The reaction was quenched with H2O (25 ml) and washed with Et2O (225 ml) to remove triphenylphosphine oxide. The aqueous phase was made acidic with 1 M HCl (?10 ml) and extracted with CH2Cl2 (525 ml). The combined organic phases were dried (MgSO4), filtered, and concentrated to give the crude material. This was triturated with EtOAc/heptane and the solids filtered and washed with EtOAc (45 ml). The filtrate was concentrated under vacuum and purified by column chromatography on silica, eluting with EtOAc/petrol/AcOH (60:35:5) to give PGF2alpha. This was dissolved in CH2Cl2 and washed with H2O (5 ml). The organic phase was then dried (MgSO4), filtered, and concentrated to give PGF2alpha (152 mg, 57% over 2 steps) as a clear, colourless oil. The 1H NMR data was consistent with that reported by Mulzer (Sheddan, N. A. et al., Org. Lett. 8, 3101-3104 (2006)). The 13C NMR data was in excellent agreement with that reported by Parve (Parve, O. et al., Bioorg. Med. Chem. Lett. 9, 1853-1858 (1999)). The IR and optical rotation data are in agreement with that reported by Mulzer (Sheddan, N. A. et al., Org. Lett. 8, 3101-3104 (2006)) and Corey (Corey, E. et al., J. Am. Chem. Soc. 92, 397-398 (1970)). Rf=0.24 (EtOAc:40/60 petroleum ether:AcOH, 60:35:5) numax (neat)/cm-1 3339, 2961, 2930, 2857, 2490, 1705, 1457, 1380, 1245, 1118, 1086, 1047, 970, 910, 878, 731 1H NMR (400 MHz; CDCl3) deltaH=0.89 (3H, t, J=6.8 Hz, CH3), 1.24-1.41 (6H, m, 3CH2), 1.43-1.54 (2H, m,), 1.54-1.63 (1H, m), 1.63-1.73 (2H, m), 1.76 (1H, m), 2.07-2.28 (5H, m), 2.28-2.39 (3H, m), 3.96 (1H, m, CHOH), 4.11 (1H, q, J=6.8 Hz, CHOH), 4.18 (1H, m, CHOH), 4.35-5.20 (1H, br. s, CO2H), 5.32-5.41 (1H, m, =CH), 5.41-5.50 (1H, m, =CH), 5.50 (1H, dd, J=15.4, 8.4 Hz, =CH), 5.58 (1H, dd, J=15.4, 6.6 Hz, =CH) 13C NMR (125 MHz; CDCl3) deltaC=14.0 (CH3), 22.6 (CH2), 24.5 (CH2), 25.2 (CH2), 25.2 (CH2), 26.3 (CH2), 31.7 (CH2), 33.1 (CH2), 36.9 (CH2), 42.7 (CH2), 50.0 (CH), 55.2 (CH), 72.3 (HCOH), 73.2 (HCOH), 77.4 (HCOH), 129.2 (=CH), 129.5 (=CH), 132.8 (=CH), 135.1 (=CH), 177.5 (C=O) HRMS (ESI) calcd for C20H34O5Na [MNa+] 377.2298. found 377.2303. [alpha]D22 -23.5 (c. 1.0, THF) (lit., 49[alpha]D20 -24.9 (c. 0.57, THF)) (lit., 51[alpha]D25 -23.8 (synthetic material) (c. 1.0, THF)) (lit., 51[alpha]D25 -23.5 (natural material) (c. 1.0, THF))

Reference： [1]Patent: WO2013/186550,2013,A1 .Location in patent: Page/Page column 85; 86
[2]Patent: US2015/158837,2015,A1 .Location in patent: Paragraph 0419-0427
[3]Organic Letters,2017,vol. 19,p. 6008 - 6011
[4]Angewandte Chemie - International Edition,2019,vol. 58,p. 9923 - 9927
Angew. Chem.,2019,vol. 131,p. 10028 - 10032,5

21
[ 50562-79-3 ]
[ 17814-85-6 ]
(E)-6-(1-tosyl-1H-indol-3-yl)hex-5-enoic acid [ No CAS ]
(Z)-6-(1-tosyl-1H-indol-3-yl)hex-5-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60 % de	Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 1.16667h; Schlenk technique; Stage #2: 1-(4-tolylsulfonyl)indole-3-carboxaldehyde In tetrahydrofuran at 20℃; for 4h; Schlenk technique; Overall yield = 64 %; Overall yield = 1.8122 g;	4.6 In a Schlenk flask, (4-carboxybutyl)triphenylphosphonium bromide (3.60 g, 8.12 mmol) was dissolved in dry THF (20 mL) and cooled to -78 °C. Sodium bis(trimethylsilyl)amide (1.0 M in THF, 16.24 mL, 16.24 mmol) was added dropwise over 10 min. The reaction mixture was warmed to 0 °C and stirred for 1 h. In a separate round-bottomed flask, 1-(toluene-4-sulfonyl)-1H-indol-3-carboxaldehyde (1.69 g, 7.38 mmol) was dissolved in dry THF (10 mL) and transferred via cannula to the reaction solution. The resulting reaction mixture was stirred at room temperature for 4 h, quenched with water (20 mL). The aqueous layer was acidified to pH 1 with HCl(aq) (2.0 M, 20 mL) and was extracted with EtOAc (3100 mL), washed with brine, dried over MgSO4 and filtered. The solvent was removed under reduced pressure to give an oil which was purified by column chromatography (petrol/ethyl acetate 7:3) to give a 4:1 mixture of (Z) and (E)-6-(1-tosyl-1H-indol-3-yl)hex-5-enoic acid as a colourless oil in (1.8122 g, 4.72 mmol, 64%). A 4:1 mixture of (Z) and (E)-6-(1-tosyl-1H-indol-3-yl)hex-5-enoic acid (0.516 g, 1.34 mmol) was dissolved in anhydrous EtOH (35 mL). Concentrated H2SO4(aq) (0.2 mL) was added, the solution was refluxed for 1.5 h, quenched into saturated NaHCO3(aq) (15 mL) and extracted with EtOAc (275 mL). The combined organic layers were washed with brine, dried over MgSO4 and filtered. The solvent was removed under reduced pressure to give an orange solid which was purified by column chromatography in (petrol/ethyl acetate 10:1) to give the product as yield as a colourless oil in (0.308 g, 0.82 mmol, 56%). Rf: 0.7 (petrol/ethyl acetate 7:3).

Reference： [1]Abualnaja, Matokah; Waddell, Paul G.; Clegg, William; Hall, Michael J. [Tetrahedron, 2016, vol. 72, # 38, p. 5798 - 5806]

22
[ 17814-85-6 ]
[ 1051373-06-8 ]
C₃₉H₃₉N₃O₃P⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at 20℃; for 24h;	1.1.3 Preparation of (1) a water-soluble mitochondrial targeting imaging probes (NMP-TPP) of 3) The product was 4-carboxybutyl triphenylphosphonium bromide and the second reaction was dissolved in THF, 20 , reaction 24h, the reaction was evaporated and the reaction solvent, the product was purified by column separation.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Institute of Chemistry (in: CAS) - CN105777637, 2016, A Location in patent: Paragraph 0119; 0120; 0121; 0122

23
[ 34328-61-5 ]
[ 17814-85-6 ]
C₁₂H₁₂ClFO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 1.75h; Inert atmosphere; Stage #2: 3-Chloro-4-fluorobenzaldehyde In tetrahydrofuran for 18h; Inert atmosphere;	1.4 Synthesis of acids 1a-1~1d-1, 1f-1, 1k-1~1n-1, 1p-1, 1aa-1, 1bb-1 (Scheme 2) General procedure: To a solution of (4-carboxybutyl)triphenylphosphonium bromide (443 mg, 1.0 mmol) in THF (15 mL), a solution of 2 M lithium bis(trimethylsilyl)amide (LHMDS) (2.5 mmol, 1.25 mL THF) was slowly added under nitrogen atmosphere at -78°C. The reaction mixture was stirred at -78°C for 15 mins, and allowed to warm slowly to 0°C for 0.5 h. After being stirred at 0°C for 1 h, a solution of appropriate aldehyde (1.05 mmol) in THF (2 mL) was slowly added at -78°C. The reaction mixture was allowed to warm slowly to 0°C and stirred at the same temperature for 18 h. The reaction was quenched with 15 mL aqueous 4 M HCl and extracted with EtOAc (3 × 5 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue in CH3OH (10 mL) was treated with 10% Pd/C (200 mg) and purged with H2. After stirring for 2 hours at room temperature, the reaction mixture was filtered through celite and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to afford the corresponding acids1a-1~1d-1, 1f-1, 1k-1~1n-1, 1p-1, 1aa-1and1bb-1.

Reference： [1]Li, Yuhang; Chen, Qi; Yang, Longhe; Li, Yanting; Zhang, Yang; Qiu, Yan; Ren, Jie; Lu, Canzhong [European Journal of Medicinal Chemistry, 2017, vol. 139, p. 214 - 221]

24
[ 17814-85-6 ]
[ 74-88-4 ]
[ 79837-79-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate In acetone at 20℃; for 10h;	1.2.1 (1) Preparation of (5-methoxy-5-oxopentyl) triphenylphosphonium bromide To a 250 ml 3-neck flask, 4-carboxybutyltriphenylphosphonium bromide (10 g, 0.02 mol, 1 eq) was added to 100 ml of acetone and stirred. K2CO3 (15 g, 0.1 mol, 5 eq) and CH3I (21 g, 0.3 mol, 15 eq) were added and stirred at room temperature for 10 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. 20 ml of ethyl acetate and 20 ml of H 2 O were added to the concentrate. The mixture was layered and washed with 20 ml of a 10% NaCl aqueous solution. After drying with Na2SO4, And concentrated under reduced pressure to obtain a brown oily compound (9.5 g, 92%).

Reference： [1]Current Patent Assignee: MIRAE FINE CHEMICAL CO LTD - KR2017/25682, 2017, A Location in patent: Paragraph 0093; 0104-0106

25
[ 17814-85-6 ]
[ 89922-82-7 ]
(Z)-8-(tert-butyldimethylsilyloxy)-5-octenoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h; Stage #2: 3-(tert-butyldimethylsilanyloxy)propionaldehyde In tetrahydrofuran at -90 - 20℃; for 3h;
63%	Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at -90 - 0℃; for 1h; Cooling with ice; Stage #2: 3-(tert-butyldimethylsilanyloxy)propionaldehyde With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at 0℃; for 3h;	To an ice-cold suspension of 4a (1.09 g, 2.46 mmol, 1.5 equiv) in THF (5.5 mL) was added NaHMDS (1.0 Min THF, 2.40 mL, 2.40 mmol, 1.5 equiv). The resulting reddish-orange mixture was stirred at 0 °C for 1 h andcooled to -95 ~ -90 °C. HMPA (1.3 mL) and a solution of aldehyde 29S7 (300 mg, 1.59 mmol, 1 equiv) in THF(1.5 mL) were added to the mixture dropwise. After 1 h, the mixture was warmed to 0 °C over 2 h and dilutedwith saturated NH4Cl. The resulting mixture was extracted with Et2O three times. The combined extracts weredried over MgSO4 and concentrated to afford a residue, which was purified by chromatography on silica gel togive olefin 34 (273 mg, 63%): Z/E 97:3; liquid; Rf 0.24 (hexane/EtOAc 4:1); 1H NMR (300 MHz, CDCl3) δ0.05 (s, 6 H), 0.89 (s, 9 H), 1.70 (quint., J = 7.5 Hz, 2 H), 2.06-2.17 (m, 2 H), 2.21-2.32 (m, 2 H), 2.36 (t, J = 7.5Hz, 2 H), 3.61 (t, J = 6.8 Hz, 2 H), 5.35-5.52 (m, 2 H); 13C-APT NMR (75 MHz, CDCl3) δ -5.2 (+), 18.4 (-),24.6 (-), 26.0 (+), 26.6 (-), 31.1 (-), 33.5 (-), 63.0 (-), 127.1 (+), 130.2 (+), 180.0 (-).

Reference： [1]Saito, Shun; Yamazaki, Takashi; Kobayashi, Yuichi [Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7636 - 7647]
[2]Suganuma, Yuta; Saito, Shun; Kobayashi, Yuichi [Synlett, 2019, vol. 30, # 3, p. 338 - 342]

26
[ 919-30-2 ]
[ 17814-85-6 ]
C₃₂H₄₅NO₄PSi⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h;	1-1 <1-1> Compound 1: Synthesis of triethoxypropylsilane-triphenylphosphonium (TPP) The cancer cell-specific biochemical inducing compound of the present inventionThe reaction was initiated by dicyclohexylcarbodiimide (DCC) as shown in Fig. 2a.Specifically, (4-carboxybutyl) triphenyl phosphate bromide((4-carboxybutyl) triphenylphosphoniumbromide)(1.00 g, 2.26 mmol), dicyclohexylcarbodiimide (0.560 g, 2.71 mmol)And 4-dimethylaminopyridine.(0.055 g, 0.450 mmol) were dissolved in 20 mL of DCM.Then, 3-aminopropyltriethoxysilane (0.5 g, 2.26 mmol)Was added to the mixed solution. The mixture was stirred at room temperature for 5 hours, and the mixture was mixed. After filtration, the residue was removed and purified using size exclusion chromatography.The compound obtained after purification was referred to as Compound 1 as triethoxypropylsilane-TPP. The compound 1 is a yellow oily phase,The yield was 0.703 g (55%).

Reference： [1]Current Patent Assignee: ULSAN NATIONAL INSTITUTE OF SCIENCE AND TECHNOLOGY - KR101907400, 2018, B1 Location in patent: Paragraph 0094-0098

27
[ 107-75-5 ]
[ 17814-85-6 ]
(Z)-12-hydroxy-8,12-dimethyltridec-5-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		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

28
[ 112-45-8 ]
[ 17814-85-6 ]
(Z)-hexadeca-5,15-dienoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 10-Undecenal In tetrahydrofuran at 0 - 20℃; for 17h; Inert atmosphere;	General procedure B: Wittig Reaction 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]Rode, Katharina; Palomba, Martina; Ortgies, Stefan; Rieger, Rene; Breder, Alexander [Synthesis, 2018, vol. 50, # 19, p. 3875 - 3885]

29
[ 2067-33-6 ]
[ 17814-85-6 ]

Yield	Reaction Conditions	Operation in experiment
66.97%	With triphenylphosphine In toluene at 110℃; for 12h; Inert atmosphere;	2.13.1 Step 1: Synthesis of (4-carboxybutyl)triphenylphosphonium bromide (aa32-2) To a solution of 5-bromopentanoic acid (10 g, 55.24 mmol,6.76 mL, 1 eq.) in toluene (100 mL) was added PPh3 (15.94 g,60.76 mmol, 1 .1 eq.). The mixture was stirred at 110 °C for 12 h under N2. The reaction progress was monitored by LCMS. Upon completion, the reaction mixture was cooled to 0 °C, then filtered and washed with toluene (10 mL 3), the filter cake was collected and dried under reduced pressure. Compound aa32-2 (16.4 g, 36.99 mmol,66.97% yield) was obtained as a white solid. LCMS (ESI): RT = 1 .076 min, mass calcd. for C22H22O2P+, 349.14 [M+H]+, found 349.2 [M+H]+. LCMS conditions: 1.5 ML/4L TFA in water (solvent A) and 0.75 ML/4L TFA in acetonitrile (solvent B), using the elution gradient 10%-80% (solvent B) over 1.35 minutes and holding at 80% for 0.9 minutes at a flow rate of 0.8 ml/min; Column: Xtimate C18 2.1 30 mm, 3 mm; Wavelength: LIV 220 nm & 254 nm Column temperature: 50 °C; 1H NMR (400 MHz, CD3CI) 5 7.91 -7.66 (m, 15H), 3.31 - 3.22 (m, 2H), 2.55 (t, J = 6.3 Hz, 2H), 1 .86-1 .82 (m, 4H) ppm.
66.97%	With triphenylphosphine In toluene at 110℃; for 12h; Inert atmosphere;	2.13.1 Step 1: Synthesis of (4-carboxybutyl)triphenylphosphonium bromide (aa32-2) To a solution of 5-bromopentanoic acid (10 g, 55.24 mmol,6.76 mL, 1 eq.) in toluene (100 mL) was added PPh3 (15.94 g,60.76 mmol, 1 .1 eq.). The mixture was stirred at 110 °C for 12 h under N2. The reaction progress was monitored by LCMS. Upon completion, the reaction mixture was cooled to 0 °C, then filtered and washed with toluene (10 mL 3), the filter cake was collected and dried under reduced pressure. Compound aa32-2 (16.4 g, 36.99 mmol,66.97% yield) was obtained as a white solid. LCMS (ESI): RT = 1 .076 min, mass calcd. for C22H22O2P+, 349.14 [M+H]+, found 349.2 [M+H]+. LCMS conditions: 1.5 ML/4L TFA in water (solvent A) and 0.75 ML/4L TFA in acetonitrile (solvent B), using the elution gradient 10%-80% (solvent B) over 1.35 minutes and holding at 80% for 0.9 minutes at a flow rate of 0.8 ml/min; Column: Xtimate C18 2.1 30 mm, 3 mm; Wavelength: LIV 220 nm & 254 nm Column temperature: 50 °C; 1H NMR (400 MHz, CD3CI) 5 7.91 -7.66 (m, 15H), 3.31 - 3.22 (m, 2H), 2.55 (t, J = 6.3 Hz, 2H), 1 .86-1 .82 (m, 4H) ppm.

Reference： [1]Current Patent Assignee: REGENERON PHARMACEUTICALS INC - WO2022/56494, 2022, A1 Location in patent: Paragraph 000552-000555
[2]Current Patent Assignee: REGENERON PHARMACEUTICALS INC - WO2022/56494, 2022, A1 Location in patent: Paragraph 000552-000555

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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 17814-85-6 ] {[proInfo.proName]}

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[ 17814-85-6 ] Synthesis Path-Upstream 1~2

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