Name: 14464-32-5|2,5-Dioxopyrrolidin-1-yl stearate|95%
Brand: Ambeed
SKU: A295188
Price: 14.0 USD
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1
[ 6066-82-6 ]
[ 57-11-4 ]
[ 14464-32-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 21h;
98%	With dicyclohexyl-carbodiimide In ethyl acetate for 6h;
95.2%	With dmap; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane at 40℃; for 8h; Inert atmosphere;	1 Synthesis Example 1 of Compound (D0) 3.00 g (26.07 mmol) of a compound A, 6.07 g (21.33 mmol) of a compound B, 5.45 g (28.44 mmol) of a condensation agent WSC.HCl, 0.29 g (2.37 mmol) of DMAP as a catalyst and 97 g of dichloromethane as a solvent were added to a three-necked flask equipped with a thermometer, a reflux tube, and a nitrogen inlet tube. After heating the reaction liquid at 40° C. for 8 hours, excess amount of pure water (PW) was added. The organic phase was washed 3 times with 100 g of PW and concentrated using an evaporator, and then obtained white crystals were washed 3 times with 100 g of methanol (MeOH) followed by drying, so as to obtain 7.75 g (yield: 95.2%) of a compound (D0)-1 represented by the chemical formula (D0-1).

90%	With dicyclohexyl-carbodiimide In tetrahydrofuran for 16h; Cooling with ice;
85%	With dicyclohexyl-carbodiimide In ethyl acetate at 35℃; for 15h;
85%	With dicyclohexyl-carbodiimide In tetrahydrofuran at 35℃; for 15h;	5.1 Synthesis of 2,5-dioxo-tetrahydropyrrole-1-stearate (13a) Stearic acid (1.00 g, 3.52 mmol) was dissolved in THF (10 mL)Dicyclohexylcarbodiimide (870 mg, 4.22 mmol)And N-hydroxysuccinimide (802 mg, 7.04 mmol)At 35 ° C for 15 hours,The reaction was poured into water (20 mL)Extraction with CH2Cl2 (20 mL), washing of the organic phase with saturated brine (20 mL)After drying over MgSO4, filtration and concentration, the product was purified by column chromatography to give a white solid (1.14 g, 85%).
83.6%	With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 14h; Cooling with ice;	1.2 2. Preparation of Intermediate NHS Stearic Acid Ester 2. Preparation of Intermediate NHS Stearic Acid Ester (0061) To a 1.000-ml round-bottom flask was added 100 g (352 mmol) of stearic acid, 60 g (521 mmol) of N-hydroxy succinimide and 800 ml of anhydrous THF. After being dissolved and ice-bath stirred, 90 g (436 mmol) of DCC was added. After 2 h stirring, the reaction continued for additional 12 h at room temperature. White solid by-product N, N-dicyclohexyl urea (DCU) was filtered off. After the resulting filtrate was evaporated to dryness, coarse products were obtained and were recrystallized with methanol at room temperature. Then 76.2 g of silver-white flake-like crystallized intermediates was obtained, with a yield of 83.6%, and m.p. 76-79° C.
80%	With N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In chloroform at 20℃;	3.2.1. N-Hydroxysuccinimide (NHS) Esters of Stearic Acid and Oleic Acid General procedure: NHS esters of fatty acids were synthesized based on the previous report [35]. Briefly, stearic acidand oleic acid (1.53 g, 5.4 mmol) were dissolved in 20 mL of chloroform. NHS (675 mg, 5.8 mmol),and EDC (1.23 g, 7.9 mmol) were added to the organic solvent. The resulting solution was stirred atroom temperature for 4 h. After removing the solvent in vacuo, the product was extracted with ethylacetate and washed with water. The organic layer was dried with magnesium sulfate and filtered;the solvent was evaporated by rotary evaporation. The product was then recrystallized and a cleanproduct was obtained at 80% yield. The product was confirmed using thin-layer chromatography(TLC, hexane/ethyl acetate 3:1).
75%	With dicyclohexyl-carbodiimide In ethyl acetate at 20℃;
74%	With dicyclohexyl-carbodiimide In ethyl acetate	10 EXAMPLE 10 EXAMPLE 10 An sulfur-containing linker compound J was prepared as follows: Stearic acid (8.53 g, 30.0 mmol) was added to a solution of N-hydroxy succinimide (3.45 g, 30.0 mmol) in dry ethyl acetate (130 ml). A solution of DCC (6.18 g, 30 mmol) in dry ethyl acetate (10 ml) was added and the reaction mixture was stirred overnight at room temperature. DCU was removed by filtration and the filtrate was concentrated under reduced pressure. Recrystallisation (ethanol) gave 2,5-dioxopyrrolidin-1-yl stearate (8.51 g, 22.3 mmol, 74%) as a white solid.
74%	With dicyclohexyl-carbodiimide In ethyl acetate at 20℃;	10 Stearic acid (8.53 g, 30.0 mmol) was added to a solution of 135 N-hydroxy succinimide (3.45 g, 30.0 mmol) in dry 9 ethyl acetate (130 ml). A solution of 136 DCC (6.18 g, 30 mmol) in dry ethyl acetate (10 ml) was added and the reaction mixture was stirred overnight at room temperature. DCU was removed by filtration and the filtrate was concentrated under reduced pressure. Recrystallisation (ethanol) gave 137 2,5-dioxopyrrolidin-1-yl stearate (8.51 g, 22.3 mmol, 74%) as a white solid.
74%	With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃;	7 To a stirred solution of the acid 137 (1 g, 3.52 mmol) in THF (10 mL) were added N- hydroxysuccinimide (567 mg, 4.92 mmol) followed by DCC (870 mg, 4.22 mmol) at 0 °C and the reaction mixture was stirred at room temperature for overnight. After completion, solid is filtered and the filtrate was evaporated under reduced pressure to get the crude material. This was recrystallized in isopropyl alcohol, filtered the solid and dried to obtain compound 140 (1 g, 74% yield) as an off white solid.1H NMR (400 MHz, CDCl3): δ 2.83 (s, 4H), 2.61 (t, J = 7.2 Hz, 2H), 1.76-1.72 (m, 2H), 1.40- 1.38 (m, 2H), 1.29-1.25 (m, 26 H), 0.89 (t, J = 6.4 Hz, 3H).
74%	With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃;	7 To a stirred solution of the acid 137 (1 g, 3.52 mmol) in THF (10 mL) were added N- hydroxysuccinimide (567 mg, 4.92 mmol) followed by DCC (870 mg, 4.22 mmol) at 0 °C and the reaction mixture was stirred at room temperature for overnight. After completion, solid is filtered and the filtrate was evaporated under reduced pressure to get the crude material. This was recrystallized in isopropyl alcohol, filtered the solid and dried to obtain compound 140 (1 g, 74% yield) as an off white solid.1H NMR (400 MHz, CDCl3): δ 2.83 (s, 4H), 2.61 (t, J = 7.2 Hz, 2H), 1.76-1.72 (m, 2H), 1.40- 1.38 (m, 2H), 1.29-1.25 (m, 26 H), 0.89 (t, J = 6.4 Hz, 3H).
70%	With N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane for 48h;	Synthesis of Stearic Acid-N-Hydroxysuccinimide Ester (C18-NHS) Stearic acid (3.0 g, 11 mmol) was dissolved in dichloromethane (100 ml) and the mixture was stirred. To this solution were added N-hydroxysuccinimide (1.5 g, 1.2 eq.) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (2.4 g, 1.2 eq.), and the mixture was stirred for 2 days. After washing twice with water, the mixture was washed once with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/3) to give the object product (2.8 g, yield 70%). The NMR measurement results of the obtained stearic acid-N-hydroxysuccinimide ester (C18-NHS) are shown below. stearic acid-N-hydroxysuccinimide ester (C18-NHS): (0199) 1H-NMR (CDCl3) δ: 2.84 (4H, m), 2.60 (2H, t, J=7.6 Hz), 1.74 (2H, q, J=7.6 Hz), 1.38 (2H, q, J=6.9 Hz), 1.43-1.20 (m, 26H), 0.88 (3H, t, J=6.8 Hz).
67%	With dicyclohexyl-carbodiimide In ethyl acetate at 20℃; for 18h; Inert atmosphere;
56%	With N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane for 48h;	P.1 Synthesis of N-succinimidyl octadecanoate Production Example 1 Synthesis of N-succinimidyl octadecanoate N-Succinimidyl octadecanoate was synthesized in accordance with the following article [N. M. Howarth, W. E. Lindsell, E. Murray, P. N. Preson, Tetrahedron 61 (2005) 8875-8887.]. Stearic acid (1.87 g, 6.56 mmol) and N-hydroxysuccinimide (0.76 g, 6.56 mmol) were dissolved in 80 mL of dichloromethane (DCM) and subjected to a reaction with 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (WSC) (1.25 g, 6.56 mmol) for 48 hours. The reaction product was then washed with water, extracted with DCM twice, and dried over MgSO2 to afford a white powder (1.4 g, 56% yield). The conversion rate of a carboxyl group in stearic acid was calculated by 1H-NMR and found to be 96%.
	With dicyclohexyl-carbodiimide In ethyl acetate at 20 - 24℃; for 12h;
	With dicyclohexyl-carbodiimide
	With dicyclohexyl-carbodiimide In tetrahydrofuran; ethyl acetate Ambient temperature;
	With dicyclohexyl-carbodiimide In ethyl acetate for 5h; Ambient temperature;
	With diisopropyl-carbodiimide In tetrahydrofuran; dichloromethane at 4℃;
	With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 12h;
	In ethyl acetate Inert atmosphere;
	In tetrahydrofuran	Example 4 N-Octadecanoyl dopamine1.42 grams stearic acid are dissolved in 10 ml tetrahydrofuran and 0.57 g N-hydroxysuccinimide and 1.03 grams dicyclohexylcarbodiimide are added. After stirring overnight, the precipitate is separated off by filtration, washed with tetrahydrofuran and the combined filtrates are freed of solvents in vacuo. Under a nitrogen atmosphere the N-octanoyloxysuccinimide thus obtained is reacted with the stoichiometric amount of dopamine hydrochloride and triethylamine (dissolved in dimethylformamide). After stirring with the exclusion of light overnight, N-octanoyl dopamine is obtained after working up.
	With N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Sonication;
	With 1,2-dichloro-ethane
	With diisopropyl-carbodiimide In dichloromethane at 20℃; for 0.25h; Inert atmosphere;
	With N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 4h;
	With dicyclohexyl-carbodiimide In ethyl acetate at 20℃; for 12h;	1. Tyrosine-lauric acid conjugate (Tyr-Lau) General procedure: Lauric acid (12.0 g, 60 mmol) dissolved in dry ethyl acetate (100 mL) was added to a solution of N-hydroxysuccinimide (NHS) (6.9 g, 60 mmol) and N,N’-dicyclohexylcarbodiimide (DCC) (12.4 g, 60 mmol) in dry ethyl acetate (300 mL). The reaction mixture was left overnight at room temperature. Dicyclohexylurea (DCU) was removed by filtration and the filtrate was evaporated under reduced pressure to yield white crystals (17.4 g, 95 % yield). Recrystallization from ethanol yielded 16.6g of pure dodecanoic acid 2,5-dioxo-pyrrolidine-1-yl ester.
	With dicyclohexyl-carbodiimide In 1,2-dimethoxyethane at 4℃; for 18h;
1.45 g	With dicyclohexyl-carbodiimide In tetrahydrofuran at 50℃; for 2h; Inert atmosphere;	Preparation 2,5-Dioxopyrrolidin-1-yl stearate Preparation 2,5-Dioxopyrrolidin-1-yl stearate A solution of stearic acid (1.00 g, 3.52 mmol) and N-hydroxysuccinimide (405 mg, 3.52 mmol) in tetrahydrofuran (15 mL) was treated dropwise with a solution of N,N'-dicyclohexylcarbodiimide (725 mg, 3.52 mmol) in tetrahydrofuran (10 mL). The mixture was heated at 50° C. under a nitrogen atmosphere for 2 h. After this time, the reaction mixture was cooled to room temperature and filtered to remove the solid dicyclohexylurea byproduct. The filtrate was concentrated under reduced pressure and dried under vacuum overnight to provide 2,5-dioxopyrrolidin-1-yl stearate (1.45 g) as a white solid: 1H NMR (300 MHz, CDCl3) δ 2.84 (s, 4H), 2.60 (t, J=7.5 Hz, 2H), 1.79-1.08 (m, 30H), 0.88 (t, J=6.6 Hz, 3H).
	In pyridine at 20℃; for 24h;	4 To a solution of stearic acid (0.5g 1.758mmol) in 5 ml dry pyridine (kept over KOH) (0.399g, 1.93mmol) and NHS (0.223 g, 1.93mmol) were added and dissolved in, stirred for 24hr at room temperature. Reaction was followed by TLC 5% MeOH. Prolinol (0.197g, 1.949mmol) were added and the mixture was stirred at room temperature for three days was added to the mixture, and stirred at room temperature. Reaction controlled by TLC (100% Ethyl acetate). At the end of the reaction, volatiles were removed under reduced pressure and the mixture was dissolved in 30 ml DCM and DCU precipitate was filtrated off and the desired product was purified using column chromatography (ethyl acetate/DCM = 1:1). Yield:1H-NMR(CDCl3, δ ppm):4.24(42^,3.67(^1^,3.51(1,2^,2.30(1,2^,2.04^,2^,1.88(^2^,1.65^,2^,1.27^,28H),0.88(t,3,H)
	With dicyclohexyl-carbodiimide In dichloromethane at 0 - 23℃; for 16h; Inert atmosphere;	4.1.1. General procedure for synthesis of NHS esters (method A) General procedure: To a solution of the appropriate fatty acid 9b, 13b-37b (1.0equiv) in CH2Cl2 (0.1 M) at 0°C was added N-hydroxysuccinimide (NHS, 1.0 equiv) and N,N'-dicyclohexylcarbodiimide (1.0 equiv). The reaction mixture was warmed to 23°C and stirred 16 h. Theresulting mixture was filtered and the filtrate was concentrated under reduced pressure to provide NHS esters 9c, 13c-37c without further purification.
	With N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride at 20℃;	2 In the first step of synthesis, stearic acid in an organic solvent of methylene chloride was reacted with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) and N-hydroxy succinimide (NHS) to obtain succinimidyl stearate.

Reference： [1]Howarth, Nicola M.; Lindsell, W. Edward; Murray, Euan; Preston, Peter N. [Tetrahedron, 2005, vol. 61, # 37, p. 8875 - 8887]
[2]Haldar, Saubhik; Karmakar, Koninika [RSC Advances, 2015, vol. 5, # 81, p. 66339 - 66354]
[3]Current Patent Assignee: TOKYO OHKA KOGYO CO LTD - US2020/4143, 2020, A1 Location in patent: Paragraph 0708-0711
[4]Location in patent: experimental part Yao, Li-Yun; Lin, Qi; Niu, Yin-Yao; Deng, Ke-Min; Zhang, Jian-Hua; Lu, Yang [Molecules, 2009, vol. 14, # 10, p. 4051 - 4064]
[5]Cui, Yanli; Li, Zhiyuan; Cheng, Zhaodong; Xia, Chengfeng; Zhang, Yongmin [Chemical Research in Toxicology, 2015, vol. 28, # 6, p. 1209 - 1215]
[6]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN104497064, 2017, B Location in patent: Paragraph 0059-0062
[7]Current Patent Assignee: SHANGHAI JIAO TONG UNIVERSITY - US2016/326096, 2016, A1 Location in patent: Paragraph 0059; 0060; 0061
[8]Kim, Hwanhee; Hu, Yiluo; Jeong, Daham; Jun, Bong-Hyun; Cho, Eunae; Jung, Seunho [Molecules, 2016, vol. 21, # 7]
[9]Menahem, Tali; Mastai, Yitzhak [New Journal of Chemistry, 2008, vol. 32, # 6, p. 925 - 928]
[10]Current Patent Assignee: BANGOR UNIVERSITY - US2014/127709, 2014, A1 Location in patent: Page/Page column
[11]Current Patent Assignee: BANGOR UNIVERSITY - US9945852, 2018, B2 Location in patent: Page/Page column 25
[12]Current Patent Assignee: VERVE THERAPEUTICS - WO2022/60871, 2022, A1 Location in patent: Paragraph 0326; 0340-0341
[13]Current Patent Assignee: VERVE THERAPEUTICS - WO2022/60871, 2022, A1 Location in patent: Paragraph 0326; 0340-0341
[14]Current Patent Assignee: BONAC CORPORATION - US9663784, 2017, B2 Location in patent: Page/Page column 42
[15]Durantie, Estelle; Bucher, Christoph; Gilmour, Ryan [Chemistry - A European Journal, 2012, vol. 18, # 26, p. 8208 - 8215]
[16]Current Patent Assignee: THE UNIVERSITY OF TOKYO - US8546487, 2013, B2 Location in patent: Page/Page column 9
[17]Suskovic, B.; Vajtner, Z.; Naumski, R. [Tetrahedron, 1991, vol. 47, # 39, p. 8407 - 8416]
[18]Matsumura, Hideo; Aizawa, Masayuki; Yokoyama, Hiroshi; Kamei, Hirotake [Chemistry Letters, 1987, p. 205 - 208]
[19]Furuta, Rhyuji; Kawata, Shigeo; Naruto, Shunsuke; Minami, Akira; Kotani, Shozo [Agricultural and Biological Chemistry, 1986, vol. 50, # 10, p. 2561 - 2572]
[20]Hasegawa; Okumura; Kiso; et al. [Agricultural and Biological Chemistry, 1980, vol. 44, # 6, p. 1309 - 1313]
[21]Bonnet; Ollivier; Gras-Masse; Melnyk [Journal of Organic Chemistry, 2001, vol. 66, # 2, p. 443 - 449]
[22]Georgiades, Savvas N.; Clardy, Jon [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 10, p. 3117 - 3121]
[23]Location in patent: scheme or table Lim, Li Yun Grace; Su, Yingying; Braet, Filip; Thordarson, Pall [Australian Journal of Chemistry, 2009, vol. 62, # 7, p. 653 - 656]
[24]Current Patent Assignee: YARD, BENITO, 67273 DACKENHEIM, DE; LOESEL; BECK - US2010/129436, 2010, A1 Location in patent: Page/Page column 4
[25]Sanchez-Ruiz, Antonio; Serna, Sonia; Ruiz, Nerea; Martin-Lomas, Manuel; Reichardt, Niels-Christian [Angewandte Chemie - International Edition, 2011, vol. 50, # 8, p. 1801 - 1804]
[26]Location in patent: scheme or table Kim, Hyun Jin; Ishii, Atsushi; Miyata, Kanjiro; Lee, Yan; Wu, Shourong; Oba, Makoto; Nishiyama, Nobuhiro; Kataoka, Kazunori [Journal of Controlled Release, 2010, vol. 145, # 2, p. 141 - 148]
[27]Location in patent: experimental part Dixit, Shailesh S.; Upadhayaya, Ram Shankar; Chattopadhyaya, Jyoti [Organic and Biomolecular Chemistry, 2012, vol. 10, # 30, p. 6121 - 6129]
[28]Tokunaga, Takeshi; Kuwahata, Kohei; Sando, Shinsuke [Chemistry Letters, 2013, vol. 42, # 2, p. 127 - 129]
[29]Avaji, Prakash G.; Jadhav, Vithal B.; Cui, Jin Xin; Jun, Yong Joo; Lee, Hwa Jeong; Sohn, Youn Soo [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 6, p. 1763 - 1767]
[30]Chen, Li-Cho; Lin, Shih-Shan; Li, Cun-Zhao; Hsu, Hsiu-Fu; Weng, Yu-Jong; Cheng, Chien-Chung [Journal of the Chinese Chemical Society, 2013, vol. 60, # 9, p. 1099 - 1102]
[31]Current Patent Assignee: 3ST RESEARCH - US2016/326182, 2016, A1 Location in patent: Paragraph 0791; 0792
[32]Current Patent Assignee: AL QUDS UNIVERSITY; Yissum Research & Development (in: Hebrew University); AL QUDS UNIV; HEBREW UNIVERSITY OF JERUSALEM - WO2009/109973, 2009, A2 Location in patent: Page/Page column 65-66
[33]Aldrich, Courtney C.; Baran, Marzena; Boshoff, Helena I. M.; Fu, Peng; Grimes, Kimberly D.; Sibbald, Paul A.; Wilson, Daniel J. [European Journal of Medicinal Chemistry, 2020, vol. 201]
[34]Current Patent Assignee: SUNBIO INC - US2021/401949, 2021, A1 Location in patent: Paragraph 0164

2
[ 14464-32-5 ]
[ 312-84-5 ]
N-stearoyl D-serine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; sodium carbonate In tetrahydrofuran; water at 35℃; for 18h;
	With sodium hydrogencarbonate In tetrahydrofuran; water at 40℃;

Reference： [1]Shinitzky, Meir; Haimovitz, Rachel [Journal of the American Chemical Society, 1993, vol. 115, # 26, p. 12545 - 12549]
[2]Menahem, Tali; Mastai, Yitzhak [New Journal of Chemistry, 2008, vol. 32, # 6, p. 925 - 928]

3
[ 14464-32-5 ]
[ 56-45-1 ]
3-hydroxy-2-stearamidopropanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydrogencarbonate In tetrahydrofuran; water at 40℃;
50%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 6h;
	With sodium hydrogencarbonate; sodium carbonate In tetrahydrofuran; water at 35℃; for 18h;

With sodium hydrogencarbonate In tetrahydrofuran; water Inert atmosphere;

Reference： [1]Menahem, Tali; Mastai, Yitzhak [New Journal of Chemistry, 2008, vol. 32, # 6, p. 925 - 928]
[2]Location in patent: experimental part Yao, Li-Yun; Lin, Qi; Niu, Yin-Yao; Deng, Ke-Min; Zhang, Jian-Hua; Lu, Yang [Molecules, 2009, vol. 14, # 10, p. 4051 - 4064]
[3]Shinitzky, Meir; Haimovitz, Rachel [Journal of the American Chemical Society, 1993, vol. 115, # 26, p. 12545 - 12549]
[4]Location in patent: scheme or table Lim, Li Yun Grace; Su, Yingying; Braet, Filip; Thordarson, Pall [Australian Journal of Chemistry, 2009, vol. 62, # 7, p. 653 - 656]

4
[ 14464-32-5 ]
[ 123-78-4 ]
(2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In tetrahydrofuran for 24h; Ambient temperature;

Reference： [1]Julina, Radomir; Herzig, Thomas; Bernet, Bruno; Vasella, Andrea [Helvetica Chimica Acta, 1986, vol. 69, p. 368 - 373]

5
[ 14464-32-5 ]
N-acetyl-glucosaminyl-β-(1->4)-N-acetyl-muramoyl-L-alanyl-D-isoglutaminyl-L-meso-diaminopimelyl-(D-amide)-(L)-D-alanyl-D-alanine [ No CAS ]
N-stearoyl PGM [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In ethyl acetate; N,N-dimethyl-formamide at 20 - 25℃; for 25h;

Reference： [1]Suskovic, B.; Vajtner, Z.; Naumski, R. [Tetrahedron, 1991, vol. 47, # 39, p. 8407 - 8416]

6
[ 14464-32-5 ]
N-acetyl-6-amino-6-deoxymuramoyl-L-alanyl-D-isoglutamine [ No CAS ]
[ 82755-85-9 ]

Yield	Reaction Conditions	Operation in experiment
48%	In N,N-dimethyl-formamide
48%	With triethylamine In N,N-dimethyl-formamide for 15h; Ambient temperature;

Reference： [1]Hasegawa; Okumura; Kiso; Azuma; Yamamura [Carbohydrate research, 1980, vol. 79, # 1, p. C20 - C23,C20-23]
[2]Hasegawa; Okumura; Kiso; et al. [Agricultural and Biological Chemistry, 1980, vol. 44, # 6, p. 1309 - 1313]

7
[ 14464-32-5 ]
2-Acetamido-6-amino-2,6-dideoxy-3-O-(D-2-propionyl-L-valyl-D-isoglutamine)-D-glucopyranose [ No CAS ]
2-Acetamido-2,6-dideoxy-3-O-(D-2-propionyl-L-valyl-D-isoglutanime)-6-stearoylamino-D-glucopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With triethylamine In 1,4-dioxane; N,N-dimethyl-formamide for 1.5h; Ambient temperature;

Reference： [1]Hasegawa; Okumura; Kiso; et al. [Agricultural and Biological Chemistry, 1980, vol. 44, # 6, p. 1309 - 1313]

8
[ 14464-32-5 ]
[ 70421-65-7 ]
N-stearoyl-L-valyl-tert-butylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78.5%	With 2-ethylmorpholine In 1,4-dioxane; dichloromethane for 48h;

Reference： [1]Zabokritskii, M. P.; Rudenko, B. A.; Chizhkov, V. P.; Mitsner, B. I.; Zvonkova, E. N. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1981, vol. 30, # 5, p. 806 - 812][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1981, # 5, p. 1045 - 1051]

9
[ 14464-32-5 ]
C₃₄H₅₈N₈O₁₈ [ No CAS ]
C₅₂H₉₁N₈O₁₉^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium hydroxide; triethylamine In N,N-dimethyl-formamide Ambient temperature;

Reference： [1]Furuta, Rhyuji; Kawata, Shigeo; Naruto, Shunsuke; Minami, Akira; Kotani, Shozo [Agricultural and Biological Chemistry, 1986, vol. 50, # 10, p. 2561 - 2572]

10
[ 14464-32-5 ]
C₃₇H₆₃N₉O₁₉ [ No CAS ]
C₅₅H₉₆N₉O₂₀^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With sodium hydroxide; triethylamine In N,N-dimethyl-formamide Ambient temperature;

Reference： [1]Furuta, Rhyuji; Kawata, Shigeo; Naruto, Shunsuke; Minami, Akira; Kotani, Shozo [Agricultural and Biological Chemistry, 1986, vol. 50, # 10, p. 2561 - 2572]

11
[ 14464-32-5 ]
H₂N-GRGRILKEPVHGV-OH [ No CAS ]
stearyl-HN-GRGRILKEPVHGV-OH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With disodium hydrogenphosphate; citrate-phosphate buffer In water; <i>tert</i>-butyl alcohol at 20℃; for 72h;

Reference： [1]Bonnet; Ollivier; Gras-Masse; Melnyk [Journal of Organic Chemistry, 2001, vol. 66, # 2, p. 443 - 449]

12
[ 14464-32-5 ]
[ 106719-44-2 ]
(R)-N^e-stearoyl-Lys(Boc) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2003,vol. 9,p. 1782 - 1794

13
[ 14464-32-5 ]
N-(2-aminoethyl)glycine methyl ester dihydrochloride [ No CAS ]
[ 625442-88-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
60%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 20h;

Reference： [1]Howarth, Nicola M.; Lindsell, W. Edward; Murray, Euan; Preston, Peter N. [Tetrahedron Letters, 2003, vol. 44, # 44, p. 8089 - 8092]
[2]Howarth, Nicola M.; Lindsell, W. Edward; Murray, Euan; Preston, Peter N. [Tetrahedron, 2005, vol. 61, # 37, p. 8875 - 8887]

14
[ 14464-32-5 ]
C₅₆H₇₄N₂O₃₀S [ No CAS ]
C₇₄H₁₀₈N₂O₃₁S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.084 g	With pyridine In water Heating;

Reference： [1]Rich, Jamie R.; Bundle, David R. [Organic Letters, 2004, vol. 6, # 6, p. 897 - 900]

15
[ 14464-32-5 ]
C₇₆H₈₂N₂O₃₀S [ No CAS ]
C₉₄H₁₁₆N₂O₃₁S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.023 g	With pyridine In water at 40℃; for 12h;

Reference： [1]Rich, Jamie R.; Bundle, David R. [Organic Letters, 2004, vol. 6, # 6, p. 897 - 900]

16
[ 14464-32-5 ]
[ 156-57-0 ]
[ 6162-69-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	With triethylamine In dichloromethane at 20℃;	10 This white solid (5.29 g, 13.9 mmol) and 139 2-mercaptoethylamine hydrochloride (2.36 g, 20.8 mmol) were dissolved in dry 29 dichloromethane (140 ml). 97 Triethylamine (4.20 g, 5.8 ml, 41.6 mmol) that was dissolved in dry dichloromethane (5 ml) was added to the solution resulting in precipitation of a white solid. The reaction was allowed to stir overnight at room temperature. The following morning 9 ethyl acetate (20 ml) and 131 ethanol (10 ml) were added to form a clear solution. The organic solution was washed with dilute acid (3×15 ml) and water (2×15 ml) and the combined organic layers were dried, filtered and evaporated. Recrystallisation (chloroform) gave 140 N-(2-mercaptoethyl)stearamide (2.66 g, 7.76 mmol, 56%) as a white solid; m.p: 63-65° C.; {Found (M+Na)+: 366.2818, C20H41NOSNa requires: 366.2806}. This showed vmax(nujol)/cm-1: 3300 (N-H), 2920 (C-H saturated), 2853 (C-H saturated), 1640 (C═O), 1550 and 1464; δH: 0.89 (3H, t, J 6.9, CH3CH2), 1.26 (28H, m), 1.64 (2H, m), 2.20 (2H, t, J 7.6, CH2CH2CO), 2.68 (2H, dt, J 6.4 and 8.4, NHCH2CH2SH), 3.45 (2H, q, J 6.2, NHCH2CH2SH) and 5.8 (1H, br s, NH); δC: 14.1, 22.7, 24.8, 25.7, 29.3, 29.4, 29.5, 29.6, 29.7, 29.7, 31.9, 36.8, 42.2 and 173.3.
	With triethylamine In dichloromethane for 2.5h;

Reference： [1]Current Patent Assignee: BANGOR UNIVERSITY - US9945852, 2018, B2 Location in patent: Page/Page column 25
[2]Eliash, Ran; Weissbuch, Isabelle; Weygand, Markus J.; Kjaer, Kristian; Leiserowitz, Leslie; Lahav, Meir [Journal of Physical Chemistry B, 2004, vol. 108, # 22, p. 7228 - 7240]

17
[ 14464-32-5 ]
[ 141-43-5 ]
[ 111-57-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine In dichloromethane for 2.5h;

Reference： [1]Eliash, Ran; Weissbuch, Isabelle; Weygand, Markus J.; Kjaer, Kristian; Leiserowitz, Leslie; Lahav, Meir [Journal of Physical Chemistry B, 2004, vol. 108, # 22, p. 7228 - 7240]

18
[ 14464-32-5 ]
N-(octadecanoyl)muramoyl-L-alanyl-D-isoglutamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: dioxane / Ambient temperature 2: NaH / dioxane 3: dicyclohexylcarbodiimide / dioxane 4: triethylamine / dioxane / Ambient temperature 5: 80percent aq. CH₃COOH 6: H₂ / palladium black / methanol / Ambient temperature

Reference： [1]Okumura; Azuma [Agricultural and Biological Chemistry, 1983, vol. 47, # 4, p. 847 - 854]

19
[ 14464-32-5 ]
[ 929-75-9 ]
13-oxo-3,6,9-trioxa-12-azatriacontanylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In chloroform at 20℃; Adding during 6 h;

Reference： [1]Current Patent Assignee: BRACCO SPA - US6342598, 2002, B1 Location in patent: Page column 32

20
[ 878389-34-5 ]
[ 14464-32-5 ]
O-(β-D-galactopyranosyl)-(1,4)-O-(β-D-glucopyranosyl)-(1,1)-(2S,3R)-2-octadecylamidopent-4-ene-1,3-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine at 60℃; for 2h;	[ O-(ß-D-GALACTOPYRANOSYL)-(1No.4)-O-(ß-D-GLUCOPYRANOSYL)-(1No.1)-(2S,3R)-] 2-octadecylamido-pent-4-ene-1, 3-diol (29): The fully deprotected disaccharide 26 (15 mg, 0.032 mmol) was dissolved in a mixture of pyridine-H2O-Et3N (10 [ML/1] [ML/0.] 2 ml), and H2S gas was bubbled into the solution overnight. The solution was evaporated to dryness. The residue was dissolved in pyridine [(5] ml), and activated ester 28 (37 mg, 0.097 mmol) was added, the mixture was stirred for 2 hours at [60°] C. The reaction was cooled and the solvent was removed under reduced pressure. The residue was pre-purified on a C 18 Sep-Pak and finally purified by HPLC on a reverse phase C8 column using a [0 No. 80% ] gradient of [MEOH-H2O] as eluent to afford compound 29 which was lyophilized (19.8 mg, 87% yield from [26). LU] NMR (CD30D, 500 MHz) : [No.5. ]84 (ddd, 1H, [J6.] 7,10. 4,17. 1 Hz, H-4_pent), 5.25 [(D'T',] 1H, [J 1.] 5,17. 2 Hz, H-5transpent), 5.11 [(D'T',] 1H, [J <] 1.5, 10.5 Hz, H-t_cis_pent), 4.33 (d, 1H, J 7.6 Hz, H-1_gal), 4.28 (d, 1H, J 7.8 Hz, H-1_glc), 4.12-4. 17 (m, [2H,] [H_3_PENT+H-LA_PENT),] 4.02 (ddd, 1H, J3.5, 4.8, 7.7 Hz, H-1b_pent), 3.90 (dd, 1H, J 2.6, 12.1 Hz, H-6a_glc), 3. 82 (dd, 1H, [J4.] 3,12. 1 Hz, H-6a_glc), 3.81 (dd, 1H, J<1, 3.3 Hz, [H-4_GAL),] 3.76 (dd, 1H, [J 7.] 5,11. 5 Hz, H-6a_gal), 3.69 (dd, 1H, [J 4.] 7,11. 4 Hz, [H-6B_GAL),] 3.51-3. 61 (m, [5H,] H-2_gal+H-3_glc+H-4_glc+H-2_pent), 3.47 (dd, 1H, [J 3.] 3,9. 8 Hz, [H-3_GAL),] 3.41 (m, 1H, [H-5_GLC),] 3.28 (dd, 1H, J 8. 0,8. 9 Hz, H- 2_glc), 2.18 (t, 1H, [J7.] 4 Hz, [COCH2),] 1.55-1. 63 (m, 2H, [COC17H35),] 1.22-1. 43 (m, 28H, [COC17H35),] 0.89 (t, 3H, J6.8 Hz, [COCI7H3S).]

Reference： [1]Current Patent Assignee: BUNDLE, David, R.; LING, Chang, Chun; ZHANG, Ping - WO2003/101937, 2003, A1 Location in patent: Page 21-22; 43-44

21
[ 497863-17-9 ]
[ 14464-32-5 ]
lactosyl ceramide (d18:2) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In methanol; chloroform at 20℃; Sodium phosphate buffer;	1 Lactosyl Ceramide (d18:2) (7). Lactosyl sphingosine (2.2 g) was dissolved in 110 mL of a solution containing chloroform-methanol-40 mM phosphate buffer (pH=7.2) (60/40/9). The N-hydroxysuccinimide stearate (13.2 g) suspended in chloroform (55 mL) and triethylamine (1.1 mL) were then added and the reaction stirred at room temperature overnight. The solution was concentrated to dryness and the residue resuspended in acetone (110 mL). A methanolic solution of 10% magnesium chloride (11 mL) was then added and the solution cooled with dry ice for 1 hour. The precipitate was filtered and washed with cold acetone yielding 3.2 g of lactosyl ceramide (7) as a white solid. HPLC (Metachem Inertsil C8 column; 85% acetonitrile/15% water, UV 205 nm), Rt=23.1 min. See, Scheme 3. Additional variations in the protocol to synthesize lactosyl ceramide are shown in Table 2.
	With triethylamine In methanol at 20℃; for 2 - 4h; Sodium phosphate buffer;	1 Lactosyl Ceramide (d18:2) (7). Lactosyl sphingosine (2.2 g) was dissolved in 110 mL of a solution containing chloroform-methanol-40 mM phosphate buffer (pH=7.2) (60/40/9). The N-hydroxysuccinimide stearate (13.2 g) suspended in chloroform (55 mL) and triethylamine (1.1 mL) were then added and the reaction stirred at room temperature overnight. The solution was concentrated to dryness and the residue resuspended in acetone (110 mL). A methanolic solution of 10% magnesium chloride (11 mL) was then added and the solution cooled with dry ice for 1 hour. The precipitate was filtered and washed with cold acetone yielding 3.2 g of lactosyl ceramide (7) as a white solid. HPLC (Metachem Inertsil C8 column; 85% acetonitrile/15% water, UV 205 nm), Rt=23.1 min. See, Scheme 3. Additional variations in the protocol to synthesize lactosyl ceramide are shown in Table 2.

Reference： [1]Current Patent Assignee: SENEB BIOSCIENCES - US2005/32742, 2005, A1 Location in patent: Page/Page column 29; sheet 4
[2]Current Patent Assignee: SENEB BIOSCIENCES - US2005/32742, 2005, A1 Location in patent: Page/Page column 29; sheet 4

22
[ 14464-32-5 ]
[ 52-90-4 ]
[ 67603-50-3 ]

Yield	Reaction Conditions	Operation in experiment
30%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 6h;

Reference： [1]Location in patent: experimental part Yao, Li-Yun; Lin, Qi; Niu, Yin-Yao; Deng, Ke-Min; Zhang, Jian-Hua; Lu, Yang [Molecules, 2009, vol. 14, # 10, p. 4051 - 4064]

23
[ 14464-32-5 ]
[ 28954-12-3 ]
N-stearoyl-L-threonine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 6h;

Reference： [1]Location in patent: experimental part Yao, Li-Yun; Lin, Qi; Niu, Yin-Yao; Deng, Ke-Min; Zhang, Jian-Hua; Lu, Yang [Molecules, 2009, vol. 14, # 10, p. 4051 - 4064]

24
[ 14464-32-5 ]
[ 61-90-5 ]
[ 14379-43-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium hydrogencarbonate In water at 0 - 20℃;
49%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 6h;

Reference： [1]Miki, Koji; Nakano, Katsuya; Matsuoka, Hideki; Yeom, Chan Joo; Harada, Hiroshi; Hiraoka, Masahiro; Ohe, Kouichi [Bulletin of the Chemical Society of Japan, 2012, vol. 85, # 12, p. 1277 - 1286]
[2]Location in patent: experimental part Yao, Li-Yun; Lin, Qi; Niu, Yin-Yao; Deng, Ke-Min; Zhang, Jian-Hua; Lu, Yang [Molecules, 2009, vol. 14, # 10, p. 4051 - 4064]

25
[ 14464-32-5 ]
[ 56-87-1 ]
Nα-stearoyl-L-lysine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 6h;

Reference： [1]Location in patent: experimental part Yao, Li-Yun; Lin, Qi; Niu, Yin-Yao; Deng, Ke-Min; Zhang, Jian-Hua; Lu, Yang [Molecules, 2009, vol. 14, # 10, p. 4051 - 4064]

26
[ 14464-32-5 ]
[ 150-30-1 ]
[ 133849-18-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 6h;

Reference： [1]Location in patent: experimental part Yao, Li-Yun; Lin, Qi; Niu, Yin-Yao; Deng, Ke-Min; Zhang, Jian-Hua; Lu, Yang [Molecules, 2009, vol. 14, # 10, p. 4051 - 4064]

27
[ 14464-32-5 ]
[ 63-91-2 ]
N-n-octadecanoyl (L)-phenylalanine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 6h;

Reference： [1]Location in patent: experimental part Yao, Li-Yun; Lin, Qi; Niu, Yin-Yao; Deng, Ke-Min; Zhang, Jian-Hua; Lu, Yang [Molecules, 2009, vol. 14, # 10, p. 4051 - 4064]

28
[ 14464-32-5 ]
[ 2577-90-4 ]
N-n-octadecanoyl methyl (L)-phenylalaninate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With pyridine at 20℃; for 24h;

Reference： [1]Location in patent: experimental part Yao, Li-Yun; Lin, Qi; Niu, Yin-Yao; Deng, Ke-Min; Zhang, Jian-Hua; Lu, Yang [Molecules, 2009, vol. 14, # 10, p. 4051 - 4064]

29
[ 14464-32-5 ]
[ 87745-27-5 ]
N-stearoyl-L-tyrosinol [ No CAS ]

Reference： [1]Molecules,2009,vol. 14,p. 4051 - 4064

30
[ 14464-32-5 ]
[ 60-18-4 ]
[ 57993-25-6 ]

Yield	Reaction Conditions	Operation in experiment
62.1%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃;	1.3 3. Preparation of NsTyr 3. Preparation of NsTyr (0063) To a white 5,000-ml round-bottom flask was added 100 g (550 mmol) of L-tyrosine, 265 g (2,500 mmol) of sodium bicarbonate, and 2,000 ml of distilled water. After being heated to dissolve, 1,000 ml of THF solution containing 100 g (262 mmol) of intermediates was added while stirring at room temperature. After TLC confirmed that the reaction had been completed, insolubles were filtered off, and the pressure of filtrate was reduced and THF was removed by evaporation. To the concentrate was added 1,000 ml of distilled water, and the pH value was adjusted to 1 with 1 mol/L HCL solution, and white solids were precipitated. To this suspension was added thermal ethyl acetate (500 ml per times). After solids dissolved, the acetic acid and ethyl ester phase were extracted. The above operation was repeated again, and the organic phases were combined. Washing was done once with saturated salt water (1,000 ml), and drying was done with anhydrous sodium sulfate. Then filtration and drying gave white coarse products from the filtrate. The coarse products were treated with methanol/acetone and recrystallized at room temperature, and 74.3 g of white solid was obtained, with a yield of 62.1%, and m.p. 100-103.4° C.
50%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 6h;

Reference： [1]Current Patent Assignee: SHANGHAI JIAO TONG UNIVERSITY - US2016/326096, 2016, A1 Location in patent: Paragraph 0059; 0062; 0063
[2]Location in patent: experimental part Yao, Li-Yun; Lin, Qi; Niu, Yin-Yao; Deng, Ke-Min; Zhang, Jian-Hua; Lu, Yang [Molecules, 2009, vol. 14, # 10, p. 4051 - 4064]

31
[ 14464-32-5 ]
[ 147-85-3 ]
[ 36577-40-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 6h;

Reference： [1]Location in patent: experimental part Yao, Li-Yun; Lin, Qi; Niu, Yin-Yao; Deng, Ke-Min; Zhang, Jian-Hua; Lu, Yang [Molecules, 2009, vol. 14, # 10, p. 4051 - 4064]

32
[ 14464-32-5 ]
[ 71-00-1 ]
[ 19132-64-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 6h;

Reference： [1]Location in patent: experimental part Yao, Li-Yun; Lin, Qi; Niu, Yin-Yao; Deng, Ke-Min; Zhang, Jian-Hua; Lu, Yang [Molecules, 2009, vol. 14, # 10, p. 4051 - 4064]

33
[ 14464-32-5 ]
[ 73-22-3 ]
[ 21400-91-9 ]

Yield	Reaction Conditions	Operation in experiment
30%	With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 6h;

Reference： [1]Location in patent: experimental part Yao, Li-Yun; Lin, Qi; Niu, Yin-Yao; Deng, Ke-Min; Zhang, Jian-Hua; Lu, Yang [Molecules, 2009, vol. 14, # 10, p. 4051 - 4064]

34
[ 14464-32-5 ]
[ 498-63-5 ]
stearoyl-prolinol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; at 20℃; for 72h;	To a solution of stearic acid (0.5g 1.758mmol) in 5 ml dry pyridine (kept over KOH) (0.399g, 1.93mmol) and NHS (0.223 g, 1.93mmol) were added and dissolved in, stirred for 24hr at room temperature. Reaction was followed by TLC 5percent MeOH. Prolinol (0.197g, 1.949mmol) were added and the mixture was stirred at room temperature for three days was added to the mixture, and stirred at room temperature. Reaction <n="67"/>controlled by TLC (100percent Ethyl acetate). At the end of the reaction, volatiles were removed under reduced pressure and the mixture was dissolved in 30 ml DCM and DCU precipitate was filtrated off and the desired product was purified using column chromatography (ethyl acetate/DCM = 1:1). Yield:1H-NMR(CDCl3, delta ppm):4.24(42^,3.67(^1^,3.51(1,2^,2.30(1,2^,2.04^,2^,1.88(^2^,1.65^,2^,1.27^,28H),0.88(t,3,H)

Reference： [1]Patent: WO2009/109973,2009,A2 .Location in patent: Page/Page column 65-66

35
[ 14464-32-5 ]
[ 62-31-7 ]
[ 105955-10-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In N,N-dimethyl-formamide Inert atmosphere; Darkness;	4 Example 4 N-Octadecanoyl dopamine1.42 grams stearic acid are dissolved in 10 ml tetrahydrofuran and 0.57 g N-hydroxysuccinimide and 1.03 grams dicyclohexylcarbodiimide are added. After stirring overnight, the precipitate is separated off by filtration, washed with tetrahydrofuran and the combined filtrates are freed of solvents in vacuo. Under a nitrogen atmosphere the N-octanoyloxysuccinimide thus obtained is reacted with the stoichiometric amount of dopamine hydrochloride and triethylamine (dissolved in dimethylformamide). After stirring with the exclusion of light overnight, N-octanoyl dopamine is obtained after working up.

Reference： [1]Current Patent Assignee: BECK; LOESEL; YARD, BENITO, 67273 DACKENHEIM, DE - US2010/129436, 2010, A1 Location in patent: Page/Page column 4

36
[ 14464-32-5 ]
C₇₃H₉₁NO₁₀ [ No CAS ]
[ 1325147-13-4 ]

Yield	Reaction Conditions	Operation in experiment
1.34 g	With triethylamine In tetrahydrofuran at 50℃; for 14h;

Reference： [1]Zhang, Zhenxing; Zhao, Wei; Wang, Bin; Xia, Chengfeng; Zhang, Wenpeng; Wang, Peng George [Organic Letters, 2011, vol. 13, # 17, p. 4530 - 4533]

37
[ 14464-32-5 ]
[ 1393355-26-4 ]
[ 1393355-27-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	In tetrahydrofuran at 20℃; for 40h; Inert atmosphere;

Reference： [1]Durantie, Estelle; Bucher, Christoph; Gilmour, Ryan [Chemistry - A European Journal, 2012, vol. 18, # 26, p. 8208 - 8215]

38
[ 14464-32-5 ]
[ 1482-97-9 ]
[ 1389347-69-6 ]

Yield	Reaction Conditions	Operation in experiment
46%		Step 1: (S)-2,3-Distearamidopropanoic acidTo a solution of <strong>[1482-97-9](S)-2,3-diaminopropanoic acid hydrochloride</strong> (1.6 g, 11.53 mmol) in H20 (40 mL ) was added NaHC03 (19.4 g, 230.66 mmol) and the mixture was stirred for 10 min. A solution of stearic acid NHS ester (11 g, 28.83 mmol) in THF (100 mL) was added and the mixture was stirred at room temperature overnight. The reaction was quenched with 3 N HCl and the white solid that precipitated was filtered. The crude white solid compound was suspended in CH2C12 and stirred vigorously for 30 min. The solid was filtered and dried under vacuum overnight to provide pure product 130 (3.3 g, 46%).1H NMR (CDC13, 300MHz): delta ppm 7.92 (bd, IH, C(O)NH), 6.58 (bt, IH, C(0)NH ), 4.34 (m, IH), 3.86 (m, IH), 3.48 (m, IH), 2.26 (m, 4H), 1.62 (m, 4H), 1.34-1.24 (m, 56H), 0.86 (t, J = 6.6 Hz, 6H).

Reference： [1]Patent: WO2012/99755,2012,A1 .Location in patent: Page/Page column 139

39
[ 14464-32-5 ]
[ 1391114-31-0 ]
[ 1391114-37-6 ]

Yield	Reaction Conditions	Operation in experiment
15%	With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Dixit, Shailesh S.; Upadhayaya, Ram Shankar; Chattopadhyaya, Jyoti [Organic and Biomolecular Chemistry, 2012, vol. 10, # 30, p. 6121 - 6129]

40
[ 14464-32-5 ]
[ 4089-07-0 ]
[ 1426701-66-7 ]

Yield	Reaction Conditions	Operation in experiment
86%		General procedure: Lauric acid (12.0 g, 60 mmol) dissolved in dry ethyl acetate (100 mL) was added to a solution of N-hydroxysuccinimide (NHS) (6.9 g, 60 mmol) and N,N?-dicyclohexylcarbodiimide (DCC) (12.4 g, 60 mmol) in dry ethyl acetate (300 mL). The reaction mixture was left overnight at room temperature. Dicyclohexylurea (DCU) was removed by filtration and the filtrate was evaporated under reduced pressure to yield white crystals (17.4 g, 95 percent yield). Recrystallization from ethanol yielded 16.6g of pure dodecanoic acid 2,5-dioxo-pyrrolidine-1-yl ester. Tyrosine ethyl ester hydrochloride (TEEH) (12.6 g, 51 mmol) was dissolved in dry chloroform (300 mL) and neutralized by addition of triethylamine (TEA) (10 mL). To this solution was added dry dodecanoic acid 2,5-dioxo-pyrrolidine-1-yl ester (15.2 g, 51 mmol) and the reaction mixture was stirred for 24 h at room temperature. Solvent was evaporated under reduced pressure. Residue was dissolved in methylene chloride (300 mL) and the solution was washed with aqueous citric acid solution. Organic solvent layer was separated, dried over MgSO4 and then evaporated to dryness to obtain the white crystalline solid, the tyrosine-lauramide conjugate (Tyr-Lau), which was further purified by silica column chromatography (EtOAc/n-Hexane 2:3). Yield: 96 percent.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1763 - 1767

41
[ 14464-32-5 ]
[ 501-36-0 ]
[ 1204614-75-4 ]

Yield	Reaction Conditions	Operation in experiment
28%	With potassium carbonate In tetrahydrofuran at 40℃; for 6h;

Reference： [1]Chen, Li-Cho; Lin, Shih-Shan; Li, Cun-Zhao; Hsu, Hsiu-Fu; Weng, Yu-Jong; Cheng, Chien-Chung [Journal of the Chinese Chemical Society, 2013, vol. 60, # 9, p. 1099 - 1102]

42
[ 14464-32-5 ]
[ 72-18-4 ]
N-octadecanoyl-L-valine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine In ethanol; water at 60 - 80℃; for 20h;

Reference： [1]Haldar, Saubhik; Karmakar, Koninika [RSC Advances, 2015, vol. 5, # 81, p. 66339 - 66354]

43
[ 14464-32-5 ]
[ 76-42-6 ]
(4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,3,4,4a,5,7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl palmitate [ No CAS ]
(4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,3,4,4a,5,7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl stearate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 10% 2: 12%	Stage #1: Oxycodone With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; Cooling with ice; Stage #2: stearic acid N-hydroxysuccinimide ester In tetrahydrofuran at 20℃;	Preparation of (4R,4aS,7aR,12bS)-4a-Hydroxy-9-methoxy-3-methyl-2,3,4,4a,5,7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl stearate and (4R,4aS,7aR,12bS)-4a-Hydroxy-9-methoxy-3-methyl-2,3,4,4a,5,7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl palmitate A suspension of oxycodone (478 mg, 1.52 mmol) in tetrahydrofuran (5 mL) was cooled in an ice bath and treated dropwise with a 1.0 M solution of potassium tert-butoxide in tetrahydrofuran (2.0 mL, 2.0 mmol). After addition was complete, the mixture was stirred at ambient temperature for 15 min. The mixture was re-cooled in the ice bath and treated dropwise with a solution of 2,5-dioxopyrrolidin-1-yl stearate (644 mg, 1.69 mmol) in tetrahydrofuran (5 mL) over 10 min. After addition was complete, the mixture was stirred at ambient temperature for 30 min. After this time, the reaction mixture was re-cooled in the ice bath, treated with saturated aqueous ammonium chloride (50 mL), and extracted with ethyl acetate (250 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 0-10% methanol/methyl tert-butyl ether) to provide material contaminated with stearic acid. This material was dissolved in methylene chloride (50 ml), washed with saturated sodium bicarbonate (225 mL) and brine (25 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. This residue was purified by reversed phase column chromatography (50 g C18 column, 30-100% acetonitrile/water) to provide two compounds. Each compound was freeze dried to afford (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,3,4,4a,5, 7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl stearate (92 mg, 10%) as a fluffy white solid: 1H NMR (300 MHz, CDCl3) δ 6.71 (d, J=8.1 Hz, 1H), 6.62 (d, J=8.1 Hz, 1H), 5.57 (dd, J=4.8, 3.9 Hz, 1H), 5.01 (s, 1H), 4.72 (br s, 1H), 3.84 (s, 3H), 3.17 (d, J=18.6 Hz, 1H), 2.85 (d, J=6.3 Hz, 1H), 2.62 (dd, J=18.9, 6.6 Hz, 1H), 2.47-2.18 (m, 8H), 2.16-2.15 (m, 2H), 1.70-1.59 (m, 3H), 1.30-1.25 (m, 28H), 0.88 (t, J=6.3 Hz, 3H); ESI MS m/z 582 [C3H55NO5+H]+; HPLC (Method A) 97.9% (AUC), tR=16.03 min; and (4R, 4aS, 7aR, 12bS)-4a-hydroxy-9-methoxy-3-methyl-2,3,4,4a,5,7a-hexahydro-1H-4,12- methanobenzofuro[3,2-e]isoquinolin-7-yl palmitate(105 mg, 12%) as a fluffy white solid: 1H NMR (300 MHz, CDCl3) δ 6.71 (d, J=8.1 Hz, 1H), 6.62 (d, J=8.4 Hz, 1H), 5.57 (dd, J=4.5, 3.6 Hz, 1H), 5.01 (s, 1H), 3.84 (s, 3H), 3.17 (d, J=18.6 Hz, 1H), 2.85 (d, J=6.3 Hz, 1H), 2.62 (dd, J=18.6, 6.3 Hz, 1H), 2.47-2.35 (m, 6H), 2.322.22 (m, 2H), 2.16- 2.15 (m, 2H), 1.68-1.59 (m, 3H), 1.30-1.25 (m, 24H), 0.88 (t, J=6.3 Hz, 3H), OH proton not observed; ESI MS m/z 554 [C34H51NO5=H]+; HPLC (Method A) 96.9% (AUC), tR=15.20 min.

Reference： [1]Current Patent Assignee: 3ST RESEARCH - US2016/326182, 2016, A1 Location in patent: Paragraph 0124; 0125

44
[ 14464-32-5 ]
tert-butyl ((4R,4aS,7aR,12bS)-4a-hydroxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl) carbonate [ No CAS ]
(4R,4aS,7aR,12bS)-9-((tert-butoxycarbonyl)oxy)-4a-hydroxy-3-methyl-2,3,4,4a,5,7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl stearate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%	Stage #1: tert-butyl ((4R,4aS,7aR,12bS)-4a-hydroxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl) carbonate With lithium hexamethyldisilazane In tetrahydrofuran for 0.5h; Cooling with ice; Stage #2: stearic acid N-hydroxysuccinimide ester In tetrahydrofuran at 0℃; for 1h;	Preparation of (4R,4aS,7aR,12bS)-9-((tert-Butoxycarbonyl)oxy)-4a-hydroxy-3-methyl-2,3,4,4a,5,7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl stearate Preparation of (4R,4aS,7aR,12bS)-9-((tert-Butoxycarbonyl)oxy)-4a-hydroxy-3-methyl-2,3,4,4a,5,7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl stearate A solution of tert-butyl ((4R,4aS,7aR,12bS)-4a-hydroxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl) carbonate (300 mg, 0.748 mmol) in tetrahydrofuran (10 mL) was cooled in an ice bath and treated dropwise with a 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1.90 mL, 1.90 mmol). After 30 min, the mixture was treated dropwise with a solution of 2,5-dioxopyrrolidin-1-yl stearate (314 mg, 0.822 mmol) in tetrahydrofuran (5 mL) and stirred at 0° C. for 1 h. After this time, the reaction mixture was poured into cold saturated aqueous ammonium chloride (10 mL) and extracted with ethyl acetate (2*25 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by reversed phase column chromatography (50 g C18 column, 10-100% acetonitrile/water) and freeze dried to provide (4R,4aS,7aR,12bS)-9-((tert-Butoxycarbonyl)oxy)-4a-hydroxy-3-methyl-2,3,4,4a,5,7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl stearate (42 mg, 8%) as a white solid: ESI LC/MS m/z 668 [C40H61NO7+H]+.

Reference： [1]Current Patent Assignee: 3ST RESEARCH - US2016/326182, 2016, A1 Location in patent: Paragraph 0793; 0794

45
[ 14464-32-5 ]
[ 29390-67-8 ]
mono[6-deoxy-6-(octadecanamido)]-β-cyclodextrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide; at 45℃; for 18h;	General procedure: Mono-6-amino-6-deoxy-beta-CD was prepared from the mono-6-O-p-toluenesulfonyl-beta-CD [36].Mono-6-amino-6-deoxy--CD (50 mg, 45 mumol) was added to NHS esters of stearic acid and oleic acid(36 mg, 90 mumol) in 1 mL of DMSO. The mixture was stirred for 18 h at 45 °C and then purified using flash chromatography (n-propyl alcohol: methanol: ethyl acetate = 7:3:3). The chemical structures ofthe fatty amido-beta-CDs were determined by MALDI-TOF spectrometry and NMR spectroscopy.

Reference： [1]Molecules,2016,vol. 21

46
[ 14464-32-5 ]
(α-D-galactopyranosyl)-(1→1)-(2S,3R,4Z)-2-amino-octadec-4-ene-1,3-diol [ No CAS ]
(α-D-galactopyranosyl)-(1→1)-(2S,3R,4Z)-2-octadecenamino-octadec-4-ene-1,3-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With triethylamine In tetrahydrofuran at 20℃; for 10h;	2.6 Synthesis of (α-D-galactopyranose) -(1 → 1) - (2S, 3R, 4Z) -2-octadecylamino-4-octadecene-1,3-diol Active ester 13a (56.3 mg, 0.144 mmol)THF (2 mL),Amine 12 (32 mg, 0.069 mmol) obtained in the previous step was usedTriethylamine (55 μL, 0.395 mmol) was added.The reaction was carried out at room temperature for 10 hours.Ethyl acetate (5 mL) was added and after workup the product was isolated by column chromatography (CH2Cl2 / MeOH: 20/1).Obtained as a white solid (35 mg, 69%)

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN104497064, 2017, B Location in patent: Paragraph 0038; 0051; 0052

47
[ 14464-32-5 ]
C₆₆H₁₀₆N₁₈O₂₆S [ No CAS ]
C₈₄H₁₄₀N₁₈O₂₈S [ No CAS ]
C₈₄H₁₃₆N₁₈O₂₇S^(4-)*4Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With sodium hydrogencarbonate In water; 1,2-dichloro-ethane; isopropyl alcohol at 20℃; for 23h;	To a stirred solution of sphingosine-p-Ala-CMG ( 2 ) -biot (VIII) (44.3 mg, 24.1 μπιο) in a mixture of water (2 mL) and 2-propanol (3 mL) 1 M aqueous sodium bicarbonate (160 μL) and a solution of N-oxysuccinimide ester of stearic acid (20.3 mg, 53 micromole) in 1 , 2-dichloroethane (0.27 mL) were added, and the mixture stirred for 8 hours at ambient temperature. Additional portions of N- oxysuccinimide ester of stearic acid (20.3 mg, 53 μτηο) in 1 , 2-dichloroethane (0.27 mL) and 1 M aqueous sodium bicarbonate (160 μL) were added and the mixture was stirred for 15 hours at ambient temperature. The reaction mixture was acidified with acetic acid (18 L) , evaporated and the residue dried in vacuum. The reaction products were separated on a silica gel column (volume 75 mL) prepared in 4:1 (v/v) chloroform/methanol and eluted with 2:6:1 (v/v/v) chloroform/methanol/water . Chromatography was accompanied by self- (0106) (0107) oxidation of the biotin group into biotin ( S-oxide ) . Repeated (twice) (0108) separation of ceramide-p-Ala-CMG ( 2 ) -biot (X), ceramide-p-Ala-CMG ( 2 ) -biot ( S- oxide) (IX) and minor sphingosine-p-Ala-CMG ( 2 ) -biot ( S-oxide ) (oxidation of unreacted sphingosine-p-Ala-CMG ( 2 ) -biot (VIII) ) on a silica gel column (volume 75 mL) prepared in 4:1 (v/v) chloroform/methanol and eluted with 1:2:1 (0109) (v/v/v) dichloromethane/ethanol/water including 1% Py provided 20.5 mg (yield 45%) of pure freeze-dried ceramide-p-Ala-CMG ( 2 ) -biot ( S-oxide ) (IX) . TLC: (0110) ceramide-p-Ala-CMG(2) -biot (X) R£ 0.62; ceramide-p-Ala-CMG ( 2 ) -biot ( S- oxide) (IX) R£ 0.54; sphingosine-p-Ala-CMG ( 2 ) -biot ( S-oxide ) R£ 0.46 (1:3:1 (v/v/v) dichloromethane/ethanol/water including 1% (v/v) Py) . (0111) NMR of ceramide-p-Ala-CMG(2) -biot (S-oxide) (IX) (700 MHz, [D2] H20/ [D4] CH3OH 2:1, 30°C) : δ 5.769 (m, 1H; CH=) , 5.454 (m, 1H; =CH) , under water (NHCH of biotin-S-oxide) , 4.721 (dd, J = 8.9, 5.5 Hz, 1H; NHCH of biotin-S-oxide ) , 4.331-3.897 (total 36H; 4 CH2COO, 12 NCH2CO, CH20, CHN, =C-CH-0) , 3.639 (d, J = 13.5, 1,9 Hz, 1H; NHCHCH of biotin-S-oxide), 3.446-3.344 (m, 7H; NCH2CH2N, CH2N of β-Ala and NHCHCH of biotin-S-oxide), 3.219 (dd, J = 13.5, 6.7 Hz, 1H; NHCHCH of biotin-S-oxide), 2.536 (broad t, 2H; CH2CO of β-Ala), 2.394 (t, J = 7.3 Hz, 2H; COCH2 of biotin-S-oxide), 2.208 (broad t, 2H; COCH2 of stearoyl), 2.030 (m, 2H; =C-CH2), 1.901 (m, 2H; COCH2CH2 of stearoyl), 1.734 and 1.593 (m, 6H; 3CH2 of biotin-S-oxide), 1.304 (broad s, 50H; 25CH2), 0.902 (t, J = 6.9 Hz, 3H; CH3), 0.894 (broad t, J = 7.1 Hz, 3H; CH3) ppm. (0112) MALDI TOF mass-spectrum of ceramide-p-Ala-CMG ( 2 ) -biot ( S-oxide ) (0113) (IX) (C84Hl4oNi8028S, MW = 1881) . M/z 1882: M+H; 1904: MNa+H; 1920: MK+H; 1926: MNa2+H; 1942: MNaK+H; 1948: MNa3+H; 1964: MKNa2+H; 1970: MNa4+H; 1986: MKNa3+H; 1992: MNa4+Na; 2008: MNa4+K. Instrument: FLEX-PC, DHB matrix.

Reference： [1]Current Patent Assignee: BOVIN, Nicolai Vladimirovich; HENRY, Stephen Micheal; TUZIKOV, Alexander Borisovich - WO2018/220603, 2018, A1 Location in patent: Page/Page column 16-17; 19-20

48
[ 14464-32-5 ]
[ 112921-00-3 ]
[ 121-44-8 ]
5'-O-[N-(stearoyl)sulfamoyl]-2',3'-O-isopropylideneadenosine triethylammonium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: stearic acid N-hydroxysuccinimide ester; ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate With caesium carbonate In N,N-dimethyl-formamide at 0 - 23℃; for 16h; Inert atmosphere; Stage #2: triethylamine In methanol; ethyl acetate	4.1.3. General procedure for acylation General procedure: To a solution of 5'-O-sulfamoyl-20,30-O-isopropylideneadenosine (1.0 equiv) in anhydrous DMF (0.1 M) at 0 Cwere added cesium carbonate (3.0 equiv) and the appropriate N-hydroxysuccinimylester 9c, 13c-56c (1.5 equiv). The mixture was warmed to 23°C and stirred for 16 h. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. Purification by flash chromatography (0-20% EtOAc/MeOH 0.5%Et3N) afforded the title compounds 9d, 13d-56d as colorless oils.

Reference： [1]Aldrich, Courtney C.; Baran, Marzena; Boshoff, Helena I. M.; Fu, Peng; Grimes, Kimberly D.; Sibbald, Paul A.; Wilson, Daniel J. [European Journal of Medicinal Chemistry, 2020, vol. 201]

49
[ 14464-32-5 ]
(S)-2,3-diaminopropionic acid [ No CAS ]
[ 1389347-69-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In ethanol; water at 75℃; for 16h;	Synthesis of Lipid Motif DTx-03-09 To a stirred solution of 03-09-2 (0.340 g, 3.8 mmol) in 65% aq. EtOH (40 mL) at RT was added slowly Et3N (2.6 mL, 19 mmol) and NHS-linear fatty acid 03-09-1 (5.2 g, 8.16 mmol). The resulting mixture was stirred at 75°C. After 16 h, the reaction mixture was neutralized with 1.5 N HC1. The precipitate was isolated by filtration, washed with water, and dried. Purification of the precipitate by trituration with DCM afforded lipid motif DTx-03-09 as an off-white solid (2.3 g, 95%). -NMR (400 MHz, TFA-d): d 0.85-0.99 (m, 6H), 1.21-1.52 (m, 56H), 1.69-1.91 (m, 4H), 2.49-2.71 (m, 4H), 4.05-4.31 (m, 2H), 4.76-5.06 (m, 1H).

Reference： [1]Current Patent Assignee: DTX PHARMA - WO2021/108640, 2021, A1 Location in patent: Paragraph 0461

50
[ 14464-32-5 ]
[ 2418-95-3 ]
N-2-octadecanoyl-N-6-tert-butoxycarbonyl-L-lysine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With triethylamine In ethanol; water at 75℃; for 16h;	1 Step 1: Synthesis of Intermediate 06-09-3 To a stirred solution of 06-09-1 (2.1 g, 8.7 mmol) in 65% aq. EtOH (50 mL) at RT was added slowly Et3N (6.1 mL, 44 mmol) and NHS-linear fatty acid 06-08-2 (5 g, 13.1 mmol). The resulting mixture was stirred at 75 °C. After 16 h, the reaction mixture was neutralized with 1.5 N HC1. The precipitate was isolated by filtration, washed with water, and dried. Purification of the precipitate by column chromatography (3% MeOH in DCM) afforded 06-09-3 as an off-white solid (2.8 g, 64%).

Reference： [1]Current Patent Assignee: DTX PHARMA - WO2021/108640, 2021, A1 Location in patent: Paragraph 0472

51
[ 14464-32-5 ]
[ 60-32-2 ]
C₂₄H₄₇NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With triethylamine In ethanol; water at 75℃; for 16h;	3 Step 3: Synthesis of Intermediate 06-09-6 To a stirred solution of 06-09-5 (5 g, 38 mmol) in 65% aq. EtOH (40 mL) at RT was added slowly Et3N (13.3 mL, 95 mmol) and NHS-linear fatty acid 06-09-2 (14.5 g, 38 mmol). The resulting mixture was stirred at 75°C. After 16 h, the reaction mixture was neutralized with 1.5 N HC1. The precipitate was isolated via filtration, washed with water, and dried, affording 06-09-6 as an off-white solid (3.5 g, 23%).

Reference： [1]Current Patent Assignee: DTX PHARMA - WO2021/108640, 2021, A1 Location in patent: Paragraph 0474

52
[ 14464-32-5 ]
[ 74381-53-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: leuprolide acetate In aq. phosphate buffer Stage #2: stearic acid N-hydroxysuccinimide ester In tetrahydrofuran at 50℃;

Reference： [1]Ngo, Hai V.; Bak, Hye-Eun; Nguyen, Hy D.; Lee, Kye Wan; Park, Chulhun; Lee, Beom-Jin [International Journal of Nanomedicine, 2023, vol. 18, p. 2325 - 2344]

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CAS No. :	14464-32-5	MDL No. :	MFCD00050403
Formula :	C₂₂H₃₉NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZERWDZDNDJBYKA-UHFFFAOYSA-N
M.W :	381.55	Pubchem ID :	3552761
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
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. 14464-32-5 ] {[proInfo.proName]}

Quality Control of [ 14464-32-5 ]

Related Doc. of [ 14464-32-5 ]

Product Details of [ 14464-32-5 ]

Safety of [ 14464-32-5 ]

Application In Synthesis of [ 14464-32-5 ]

[ 14464-32-5 ] Synthesis Path-Downstream 1~52

Related Functional Groups of
[ 14464-32-5 ]

Amides

Esters

Related Parent Nucleus of
[ 14464-32-5 ]

Pyrrolidines

Precautionary Statements-General

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Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 14464-32-5 ] {[proInfo.proName]}

Quality Control of [ 14464-32-5 ]

Related Doc. of [ 14464-32-5 ]

Product Details of [ 14464-32-5 ]

Safety of [ 14464-32-5 ]

Application In Synthesis of [ 14464-32-5 ]

[ 14464-32-5 ] Synthesis Path-Downstream 1~52

Related Functional Groups of [ 14464-32-5 ]

Amides

Esters

Related Parent Nucleus of [ 14464-32-5 ]

Pyrrolidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 14464-32-5 ]

Related Parent Nucleus of
[ 14464-32-5 ]