Name: 1069-79-0|(2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl distearate|95%
Brand: Ambeed
SKU: A799800
Price: 32.0 USD
Availability: InStock
Rating: 99 (35 reviews)

1
[ 4004-05-1 ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; platinum Hydrogenation;

Reference： [1]Baer; Buchnea [Journal of the American Chemical Society, 1959, vol. 81, p. 1758,1761]

2
[ 22430-36-0 ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium platinum; acetic acid Hydrogenation;

Reference： [1]Baer et al. [Journal of the American Chemical Society, 1952, vol. 74, p. 152,155]

3
[ 10567-21-2 ]
[ 32159-15-2 ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	(i) Py, CHCl₃, (ii) Zn, AcOH, Et₂O; Multistep reaction;

Reference： [1]Pfeiffer; Hoke; Miao; Tedeschi; Pasternak; Hahn; Erickson; Levin; Burton; Weisbach [Journal of medicinal chemistry, 1971, vol. 14, # 6, p. 493 - 499]

4
[ 26531-41-9 ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen

Reference： [1]Aneja,R. et al. [Tetrahedron Letters, 1969, p. 4183 - 4186]

5
1,2-dilinoleoyl-sn-glycero-3-phosphoethanolamine [ No CAS ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen

Reference： [1]Dorofeeva,L.T. et al. [Journal of general chemistry of the USSR, 1963, vol. 33, p. 2807 - 2809][Zhurnal Obshchei Khimii, 1963, vol. 33, p. 2880 - 2883]

6
[ 1069-79-0 ]
[ 123252-11-9 ]
[ 173912-50-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine In tetrahydrofuran at 65℃;

Reference： [1]Alcaraz, Marie-Lyne; Peng, Ling; Klotz, Philippe; Goeldner, Maurice [Journal of Organic Chemistry, 1996, vol. 61, # 1, p. 192 - 201]

7
[ 115265-94-6 ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With trifluoroacetic acid In dichloromethane Ambient temperature;

Reference： [1]Alcaraz, Marie-Lyne; Peng, Ling; Klotz, Philippe; Goeldner, Maurice [Journal of Organic Chemistry, 1996, vol. 61, # 1, p. 192 - 201]

8
[ 1069-79-0 ]
(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-(10-oxo-decyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester [ No CAS ]
(2S,3S,4S,5R,6R)-6-(10-{2-[((R)-2,3-Bis-octadecanoyloxy-propoxy)-hydroxy-phosphoryloxy]-ethylamino}-decyloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride In methanol; chloroform at 58℃; for 0.5h; Yield given;

Reference： [1]Sun, Lijun; Chaikof, Elliot L. [Carbohydrate Research, 1998, vol. 307, # 1-2, p. 77 - 81]

Yield	Reaction Conditions	Operation in experiment
	Synthese;

10
[ 1069-79-0 ]
[ 530-62-1 ]
Octadecanoic acid (R)-2-(hydroxy-{2-[(imidazole-1-carbonyl)-amino]-ethoxy}-phosphoryloxy)-1-octadecanoyloxymethyl-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In toluene at 100℃; for 1h;

Reference： [1]Maeda, Noriyuki; Takeuchi, Yoshito; Takada, Miki; Namba, Yukihiro; Oku, Naoto [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 4, p. 1015 - 1017]

11
[ 1069-79-0 ]
[ 106520-77-8 ]
Octadecanoic acid (R)-2-{hydroxy-[2-(3-methylsulfanyl-propionylamino)-ethoxy]-phosphoryloxy}-1-octadecanoyloxymethyl-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With triethylamine In chloroform

Reference： [1]Zhang, Jianbing; Jing, Bingwen; Tokutake, Nobuya; Regen, Steven L. [Journal of the American Chemical Society, 2004, vol. 126, # 35, p. 10856 - 10857]

12
[ 1069-79-0 ]
[ 769193-58-0 ]
Octadecanoic acid (R)-2-[(2-{2-[2-({2-[((R)-2,3-bis-octadecanoyloxy-propoxy)-hydroxy-phosphoryloxy]-ethylcarbamoyl}-methylsulfanyl)-ethylsulfanyl]-acetylamino}-ethoxy)-hydroxy-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With triethylamine In chloroform

Reference： [1]Zhang, Jianbing; Jing, Bingwen; Tokutake, Nobuya; Regen, Steven L. [Journal of the American Chemical Society, 2004, vol. 126, # 35, p. 10856 - 10857]

13
[ 10567-21-2 ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) Et₃N, POCl₃, 2.) Et₃N / 1.) THF, 0 deg C - room temperature, 2.) THF, 0 deg C - room temperature 2: 93 percent / TFA / CH₂Cl₂ / Ambient temperature
	Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran 2: sodium azide / N,N-dimethyl-formamide / 85 °C 3: palladium on activated charcoal; hydrogen; acetic acid / methanol
	Multi-step reaction with 2 steps 1.1: 1,2,3-triazole / dichloromethane / 1 h / 25 °C 1.2: 2 h / 25 °C 1.3: 0.5 h / -5 - 0 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / 25 °C

Reference： [1]Alcaraz, Marie-Lyne; Peng, Ling; Klotz, Philippe; Goeldner, Maurice [Journal of Organic Chemistry, 1996, vol. 61, # 1, p. 192 - 201]
[2]Song, Yang; Yuan, Wei; Luo, Yu; Lu, Wei [Chinese Chemical Letters, 2012, vol. 23, # 2, p. 154 - 156]
[3]Current Patent Assignee: ANQING RUNKE BIOLOGICAL MEDICINE TECH - CN108727426, 2018, A

14
[ 1069-79-0 ]
4-(3-<2-<((2,3-bis(octadecanoyloxy)propoxy)hydroxyphosphoryl)oxy>ethyl>-1-methylureido)benzenediazonium trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 91 percent / Et₃N / tetrahydrofuran / 65 °C 2: 2.) aq. NaNO₂ / 1.) MeOH, CHCl₃, room temperature, 1 h

Reference： [1]Alcaraz, Marie-Lyne; Peng, Ling; Klotz, Philippe; Goeldner, Maurice [Journal of Organic Chemistry, 1996, vol. 61, # 1, p. 192 - 201]

15
[ 173912-48-6 ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 90 percent / DDQ / CH₂Cl₂; H₂O / Ambient temperature 2: 1.) Et₃N, POCl₃, 2.) Et₃N / 1.) THF, 0 deg C - room temperature, 2.) THF, 0 deg C - room temperature 3: 93 percent / TFA / CH₂Cl₂ / Ambient temperature

Reference： [1]Alcaraz, Marie-Lyne; Peng, Ling; Klotz, Philippe; Goeldner, Maurice [Journal of Organic Chemistry, 1996, vol. 61, # 1, p. 192 - 201]

16
L-(+)-Dilinoleoyl-N-phthaloyl-α-kephalin [ No CAS ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. NaOH, N₂H₄*H₂O 2: H₂ / PtO₂

Reference： [1]Dorofeeva,L.T. et al. [Journal of general chemistry of the USSR, 1963, vol. 33, p. 2807 - 2809][Zhurnal Obshchei Khimii, 1963, vol. 33, p. 2880 - 2883]

17
[ 17966-16-4 ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2,4,6-triisopropyl-benzenesulfonyl chloride, Py / CHCl₃ 2: H₂ / Pd-C

Reference： [1]Aneja,R. et al. [Tetrahedron Letters, 1969, p. 4183 - 4186]

18
[ 1069-79-0 ]
[ 59156-70-6 ]
1,2-distearoyl-sn-glycero-3-phosphoethanolamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In chloroform; N,N-dimethyl-formamide at 20℃; for 2h;	1 To a solution of bis (N-hydroxysuccinimidyl) adipate (A) (70 itig, 205 μmol) in dry N,N-dimethylformamide (1.5 ml) were added DOPE or DSPE (L) (40 μmol) in chloroform (1.5 ml) followed by triethylamine (7 μl) . The mixture was kept for 2 h at room temperature, then neutralized with acetic acid and partially concentrated in vacuo.Column chromatography (Sephadex LH-20, 1:1 chloroform- methanol, 0.2% acetic acid) of the residue yielded the activated lipid (A-L) (37 mg, 95%) as a colorless syrup; TLC (chloroform-methanol-water, 6:3:0.5): Rf = 0.5 (DOPE-A; III), Rf = 0.55 (DSPE-A) . i1H NMR (CDCI3/CD3OD, 2:1) , δ:DSPE-A - 5.39 (m, IH, -OCH2-CHO-CH2O-) , 4.53 (dd, IH, J=3.42, J=Il.98, -CCOOHCH-CHO-CH2O-) , 4.33 (dd, IH, J=6.87, J=Il.98, - CCOOHCH-CHO-CH2O-) , 4.23 (m, 2H, PO-CH2-CH2-NH2) , 4.15 (m, 2H, -CH2-OP) , 3,61 (m, 2H, PO-CH2-CH2-NH2) , 3.00 (s, 4H, ONSuc) , 2.81 (m, 2H, -CH2-CO (Ad) , 2.48 (m, 4H, 2x (-CH2-CO) , 2.42 (m, 2H, -CH2-CO (Ad) , 1.93 (m, 4H, COCH2CH2CH2CH2CO) , 1.78 (m, 4H, 2X(COCH2CH2-) , 1,43, 1.47 (2 bs, 4OH, 20CH2) , 1.04 (m, 6H, 2CH3) .DOPE-A (III) - 5.5 (m, 4H, 2x( -CH=CH-) , 5.39 (m, IH, -OCH2- CHO-CH2O-) , 4.58 (dd, IH, J=3.67, J=Il.98, -CCOOHCH-CHO-CH2O- EPO ) , 4.34 (dd, IH, J=6.61, J=Il.98, -CCOOflCH-CHO-CH^-) , 4.26 (m, 2H, PO-CH2-CH2-NH2) , 4.18 (m, 2H, -CH2-OP) , 3.62 (m, 2H,PO-CH2-CH2-NH2) , 3.00 (s, 4H, ONSuc) , 2.8 (m, 2H, -CH2-CO (Ad) ,2.50 (m, 4H, 2x (-CH2-CO) , 2.42 (m, 2H, -CH2-CO (Ad) , 2.17 (m, 8H, 2x (-CH2-CH=CH-CH2-) , 1.93 (m, 4H, COCH2CH2CH2CH2CO) , 1.78 (m, 4H, 2X(COCH2CH2-) , 1,43, 1.47 (2 bs, 4OH, 20CH2) , 1.04 (m,6H, 2CH3) .

Reference： [1]Current Patent Assignee: KODE BIOTECH LIMITED - WO2007/35116, 2007, A1 Location in patent: Page/Page column 20-21

19
[ 1069-79-0 ]
[ 76931-93-6 ]
[ 1040392-36-6 ]

Yield	Reaction Conditions	Operation in experiment
7.25%	With triethylamine In chloroform at 20℃;	11 FIG. 11 shows synthesis of SATA-DSPE.[0120] 25 mg (33.4 μmol) of DSPE in 2 mL chloroform was added to 17 μL (0.12 mmol) triethylamine in a vial with a stir-bar. 11.6 mg (50.2 μmol) of SATA was added to the mixture while stirring under argon at room temperature. The solution was stirred overnight, then TLC was performed with a mobile phase of chloroform, methanol, and water in 65/25/4 v/v/v ratio. The fluorescamine test for amines was negative for the crude mixture. [0121] The crude was placed in a test tube with 2 mL of chloroform, a drop of methanol, and 4 mL of 18 Mω water. The solution was centrifuged at 2000 rpm for 5 minutes, after which the aqueous phase was decanted and 4 mL of water was added. This process was repeated a total of four times. The aqueous phase fractions were added together, dried under reduced pressure and resuspended in chloroform.[0122] TLC was performed on the fractions and the product was visualized using a phosphorous spray. The fraction containing product were combined and dried under vacuum. The product was stored under chloroform. The concentration was determined by first deprotecting the sulfhydryl group with hydroxylamine from a procedure according to Pierce, then performing the DTNB test (Ellman, G.L (1959). Tissue Sulfhydryl Groups. Arch. Biochem. Biophys. 82, 70-77.; Riddles, P.W., Blakeley, R. L. Zerner, B. (1983) Reassessment of Ellman's Reagent. Methods Enzymol. 91. 49-60.). The yield was 2.14 mg, 7.25% of the desired phospholipid. ES-MS m/z: 909.6 ([M+Na+]), calculated is 909 for C45H85NNa2Oi0PS.

Reference： [1]Current Patent Assignee: SUNGWOO ELECTRONICS CO.,LTD. - WO2008/91655, 2008, A2 Location in patent: Page/Page column 26; Sheet 11

20
[ 108-55-4 ]
[ 1069-79-0 ]
[ 1009838-54-3 ]

Yield	Reaction Conditions	Operation in experiment
39.3%	With triethylamine In chloroform at 20℃; for 12h;	6 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (DSPE) was purchased from Sygena. Glutaric anhydride (97%) and triethylamine (99.5%) were purchased from Aldrich. All reagents were used without further purification. A three-fold molar excess of glutaric anhydride (465 mg, 4.08 mmol) and four-fold molar excess of triethylamine (5.44 mmol) were added to DSPE (1.02 g, 1.36 mmol) in anhydrous chloroform and the resulting mixture stirred under argon at room temperature for 12 h. The reaction mixture was washed with 0.1% acetic acid (2) water (2) and pH 9 NaHCO3 the CHCl3 fraction was chromatographed on a silica column using hexanes/ethyl acetate (2:1). The solvent was removed under vacuum to yield a white cake (460 mg, 39.3% theoretical). Product purity was confirmed by TLC and 1H-NMR. The product gave a negative response to fluorescamine dye indicating complete 1° amine funtionalization. Analytical data: TLC mobile phase hexanes/ethyl acetate (2:1) Rf=0.45, 1H-NMR (CDCl3, 400 MHz) δ0.883 (t, 3H, CH2-CH3), 1.26 (s, 56H, CH2), 1.61 (br, 4H, O-OC-CH2-CH2), 1.95 (q, 2H, CO-CH2-CH2-CH2-CO), 2.30 (m, 4H, CO-CH2-CH2-CH2-CO, 4H, O-OC-CH2-CH2), 3.37 (q, 4H, P-O-CH2-COH2), 4.16 (q, 1H, CO-O-CH2-CHOCH2), 4.38 (q, 1H, CO-O-CH2'-CHOCH2), 5.23 (br, 1H, CO-O-CH2-CHOCH2). The Glu-DSPE derivative can be activated with NHS/DCC and modified with bis(3-aminopropyl) terminated poly(ethylene glycol) (Aldrich, Milwaukee, Wis.). The amino-poly(ethylene glycol)-DSPE can be modified with 1,4,7,10 tetraazacyclododecane-1,4,7-tris(acetic acid-t-butyl ester)-10-acetic acid mono (N-hydroxysuccinimidyl ester) to give the DOTA-PEG-DSPE derivative. Gadolinium can then be inserted into the chelate by incubating the conjugate with gadolinium oxide at 95° C. overnight at pH 7-8. Free gadolinium is then removed on a Sephadex G-75 column.
	With dmap; triethylamine In chloroform at 60℃; for 4h;	33 To the solution of 5 mL of chloroform was added 100 mg of 1,2-distearoyl-sn-glyvero-3-phosphoethanolamine (DSPE, 0.133 mmol), 36 mg of 4-dimethylamino pyridine (DMAP, 0.294 mmol), 17 mg of glutaric anhydride (0.147 mmol), and 28 μL of triethylamine (TEA). The reaction mixture was stirred at 60° C. for 4 hours. DSPE was precipitated by the addition of 20 mL of acetone and the product was collected by filtration.

Reference： [1]Current Patent Assignee: CALIFORNIA PACIFIC MEDICAL CENTER - US2005/112065, 2005, A1 Location in patent: Page/Page column 11
[2]Current Patent Assignee: UNIVERSITY OF UTAH - US2011/269713, 2011, A1 Location in patent: Page/Page column 52; 53

21
[ 1069-79-0 ]
C₁₉H₃₁NO₄S [ No CAS ]
[ 1227472-65-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine

Reference： [1]Burdinski, Dirk; Pikkemaat, Jeroen A.; Emrullahoglu, Mustafa; Costantini, Francesca; Verboom, Willem; Langereis, Sander; Gruell, Holger; Huskens, Jurriaan [Angewandte Chemie - International Edition, 2010, vol. 49, # 12, p. 2227 - 2229]

22
[ 108-55-4 ]
[ 1069-79-0 ]
[ 1186057-85-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dmap; triethylamine / chloroform / 4 h / 60 °C 2: dicyclohexyl-carbodiimide / chloroform / 20 °C

Reference： [1]Current Patent Assignee: UNIVERSITY OF UTAH - US2011/269713, 2011, A1

23
C₄₁H₇₉N₃O₈P^(1-)*Na⁽¹⁺⁾ [ No CAS ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With palladium on activated charcoal; hydrogen; acetic acid In methanol

Reference： [1]Location in patent: scheme or table Song, Yang; Yuan, Wei; Luo, Yu; Lu, Wei [Chinese Chemical Letters, 2012, vol. 23, # 2, p. 154 - 156]

24
[ 1069-79-0 ]
[ 910449-50-2 ]
3-({2-[4-(3,9-bis(carboxymethyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1⁽¹⁴⁾,11⁽¹⁵⁾,12-trien-6-yl)-4-carboxybutyryl-amino]ethoxy}hydroxyphosphoryloxy)-2-(octadecanoyloxy)propyl octadecanoate, gadolinium complex of [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(3,9-bis(carboxymethyl)-3,6,9,15-tetraazabicyclo-[9.3.1]pentadeca-1⁽¹⁴⁾,11⁽¹⁵⁾,12-trien-6-yl)pentanedioic acid, gadolinium complex of With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine In pyridine; N,N-dimethyl-formamide at 20℃; for 20h;	5.a a) Gadolinium complex of the 3-({2-[4-(3,9-bis(carboxymethyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(14),11(15),12-trien-6-yl)-4-carboxybutyryl-amino]ethoxy}hydroxyphosphoryloxy)-2-(octadecanoyloxy)propyl ester of octadecanoic acid 200 mg of the compound obtained in stage c) of Example 3 are dissolved in 10 ml of dimethylformamide. 204 mg of N,N'-dicyclohexylcarbodiimide and 40 mg of N-hydroxysuccinimide are added to this solution. The mixture is stirred at ambient temperature for 1 h and a solution of 250 mg of 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (DSPE, AVANTI Polar Lipids, Inc.) in 5 ml of pyridine is added. The reaction medium is stirred at ambient temperature for 20 h and then precipitated from 50 ml of ethanol. The product is subsequently purified on silica gel. w=190 mg.m/z: ES- 1335

Reference： [1]Current Patent Assignee: GUERBET - US8268810, 2012, B2 Location in patent: Page/Page column 26-27

25
[ 1415981-79-1 ]
[ 1069-79-0 ]
(2R)-3-((((2,2-dimethyl-4,44-dioxo-3,8,11,14,17,20,23,26,29,32,35,38,41-tridecaoxa-5,45-diazaheptatetracontan-47-yl)oxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl distearate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With N-ethyl-N,N-diisopropylamine; HATU In methanol; chloroform; water at 25℃; for 4h; Inert atmosphere;	16.1 l,2-distearoyl-sn-glycero-3-phosphoethanolamine (200 mg, 0.267 mmol), t- Boc-N-amido-dPEGi2-acid (21 1 mg, 0.294 mmol) and N,N,N',N'-Tetramethyl-0-(7- azabenzotriazol- 1 -yl)uronium hexafluorophos-phate (122 mg, 0.320 mmol) were dissolved in a chloroform/methanol/H20 (6 mL, 65:35:8) in a 20 mL scintillation vial flushed with argon. N,N-Diisopropylethylamine (116 uL, 0.668 mmol) was added. Reaction was allowed to stir at 25°C for 4 hours and concentrated. Material was then purified via silica gel chromatography with a dichloromethane/methanol gradient to yield (2R)-3-((((2,2-dimethyl-4,44-dioxo- 3,8, 1 l, 14, 17,20,23,26,29,32,35,38,41-tridecaoxa-5,45-diazaheptatetracontan-47- yl)oxy)(hydroxy)phosphoryl)oxy)propane-l,2-diyl distearate as an oil (252 mg, 65%).

Reference： [1]Current Patent Assignee: NITTO DENKO CORPORATION - WO2012/170952, 2012, A2 Location in patent: Page/Page column 67; 68

26
[ 1069-79-0 ]
[ 880129-82-8 ]
[ 1462237-41-7 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 2-((17-azido-3,6,9,12,15-pentaoxaheptadec-1-yl)oxy)acetic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine In chloroform; N,N-dimethyl-formamide at 50℃; for 1.5h; Inert atmosphere;

Reference： [1]Gianella, Anita; Mieszawska, Aneta J.; Hoeben, Freek J. M.; Janssen, Henk M.; Jarzyna, Peter A.; Cormode, David P.; Costa, Kevin D.; Rao, Satish; Farokhzad, Omid C.; Langer, Robert; Fayad, Zahi A.; Mulder, Willem J. M. [Chemical Communications, 2013, vol. 49, # 82, p. 9392 - 9394]

27
[ 1069-79-0 ]
C₁₉H₂₉N₄O₁₀^(3-)*Gd⁽³⁺⁾ [ No CAS ]
C₆₀H₁₀₉N₅O₁₇P^(3-)*Gd⁽³⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In pyridine; water at 40 - 80℃; for 24h;	3.1 EXAMPLE 3.1 DOTA-DSPE 200 mg of DOTA-Gd carboxylate are dissolved in 1.5 ml of water. 238 mg of 1,2-dioctadecanoyl-sn-glycero-3-phosphoethanolamine (DSPE) dissolved in 70 ml of pyridine at 80° C. are added, along with 85 mg of EDCI and 22 mg of HOBT. The reaction medium is stirred at 40° C. for 24 hours. The pyridine is then evaporated off and the residue is taken up in ethanol and then filtered. C60H108GdN5O17P; m/z (ES-)=1358

Reference： [1]Current Patent Assignee: UNIVERSITY OF BORDEAUX 1; GUERBET - US2013/309176, 2013, A1 Location in patent: Paragraph 0261; 0262

28
[ 1069-79-0 ]
C₄₀H₇₉N₃O₂₁ [ No CAS ]
C₈₁H₁₅₉N₄O₂₈P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: C₄₀H₇₉N₃O₂₁ With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine In chloroform; N,N-dimethyl-formamide at 50℃; for 2h; Inert atmosphere;

Reference： [1]Gianella, Anita; Mieszawska, Aneta J.; Hoeben, Freek J. M.; Janssen, Henk M.; Jarzyna, Peter A.; Cormode, David P.; Costa, Kevin D.; Rao, Satish; Farokhzad, Omid C.; Langer, Robert; Fayad, Zahi A.; Mulder, Willem J. M. [Chemical Communications, 2013, vol. 49, # 82, p. 9392 - 9394]

29
[ 1069-79-0 ]
[ 586-89-0 ]
C₅₀H₈₈NO₁₀P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-acetyl-benzoic acid With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h; Stage #2: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine With triethylamine In dichloromethane at 20℃; for 6h;	Synthesis of DSPE-4-acetylbenzoic acid: 4-acetylbenzoicacid (30 mg), DCC (28.8 mg), and NHS (16.1 mg) were dissolved in 2ml dichloromethane. The mixture was reacted at room temperature for 6 h before DSPE (70 mg)and triethylamine were added to the solution. After stirring at room temperature for another 6 h, the product was extracted by adding water and dichloromethane in the reaction mixture. The organic phase was dried by Na2SO4 and evaporated using a vacuum rotary evaporator.The residue was purified by silica gel chromatography.

Reference： [1]Du, Jiang-Bo; Song, Yan-Feng; Ye, Wei-Liang; Cheng, Ying; Cui, Han; Liu, Dao-Zhou; Liu, Miao; Zhang, Bang-Le; Zhou, Si-Yuan [Anti-Cancer Drugs, 2014, vol. 25, # 7, p. 751 - 766]

30
[ 1069-79-0 ]
[ 68528-80-3 ]
C₅₃H₉₇N₂O₁₃P [ No CAS ]

Reference： [1]Molecular Pharmaceutics,2015,vol. 12,p. 769 - 782

31
[ 1069-79-0 ]
[ 1222468-90-7 ]
3-((hydroxy(2-(3-(4-(3-(3,14,25-trihydroxy-2,10,13,21,24-pentaoxo-3,9,14,20,25-pentaazatriacontan-30-yl)thioureido)phenyl)thioureido)ethoxy)phosphoryl)oxy)propane-1,2-diyldistearate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In chloroform; dimethyl sulfoxide at 50℃; for 72h; Inert atmosphere;	3 Synthesis of3-((hydroxy(2-(3-(4-(3-(3,14,25-trihydroxy-2,1O, 13,21,24-pentaoxo-3,9,14,20,25- pentaazatri-acontan-30-yl) thioureido)phenyl) thioureido)ethoxy)phos-phoryl)oxy)propane-1, 2- diyldi-stearate [0138j To a solution of DFO-NCS (7, 6.0 mg, 8.0 jimol) in dimethyl sulfoxide (0.5 ml) was added 1,2-distearoyl-sn-glycero-3- phosphoethanolamine (DSPE, 1, 9.9 mg, 13.2 jimol), chloroform (0.5 ml) and diisopropylethyl amine (20.0 jiL). The mixture was stirred at 50 °C under nitrogen for three days, after which time chloroform was evaporated and 1 M Tris was added (0.5 ml). Half an hour later, the suspension was filtered and the resulting solid washed with 1 M Tris (2 x 1 ml), water (3 x 1 ml)and dichloromethane (3 x 1 ml). The white solid was dried to afford the title product (11.1 mg, 85 %). 1H-NMR (Tris salt, CDCI3/DMSO-d6):0.91 (t, 6H), 1.25 (bs, 62H), 1.37 (m, 4H), 1.52 (m, 12H), 1.99 (s, 3H), 2.22 (m, 4H), 2.35 (m, 4H), 2.64 (m, 4H), 3.04 (m, 4H), 3.47 (bs, 8H), 3.51 (s, 6H), 3.68 (m, 2H), 3.82 (bs, 2H), 3.88 (bs, 2H), 4.05 (m, 1H), 4.28 (m, 1H), 5.07 (m, 1H), 5.10 (bs, 3H), 7.22 (d, 2H), 7.34 (bs, 3H), 7.59 (s, 1H),7.66 (bs, 4H), 7.72 (bs, 1H), 9.23 (s, 1H), 9.50 (bs, 1H), 9.69 (s, 1H), 9.76 (s, 1H), 9.82 (bs, 1H). HRMS FAB [M-Hr: mlz 1498.8977 (calculated for 4H133N9016PS2 1498.9049).

Reference： [1]Current Patent Assignee: ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI - WO2015/183876, 2015, A1 Location in patent: Paragraph 0138

32
[ 1069-79-0 ]
[ 1427004-19-0 ]
3-((((23-(11,12-dehydrodibenzo[b,f]azocin-S(GH)-yl)-4,20,23-trioxo-7,10,13,16-tetraoxa-3,19-diazatricosyl)oxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyldistearate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 40℃; for 15h; Inert atmosphere;	3 Synthesis of3-{({(23-(1 1, 12-dehydrodibenzo[bj] azocin-S (GH)-yl)-4, 20, 23-trioxo- 7,10,13,16- tetraoxa-3, 19-diazatricosyl)oxy) (hydroxy)phosphoryl)oxy)propane-1, 2- diyldistearate [0136j A solution of DBCO NHS ester (2, 12.8 mg, 19.7 jimol), 1,2- distearoyl-snglycero-3-phosphoethanolamine (DSPE, 1, 16.2 mg, 21.7 jimol), and diisopropylethyl amine (5.4 iL) in dry dichloromethane (2 ml) was prepared in a round bottom flask equipped with a condenser. The system was purged with nitrogen and the mixture stirred at 40 °C for 15 hours. The resulting solution was chromatographed on silica gel, using gradient elution from neat dichloromethane to dichloromethane/methanol 5:1 to obtain the desired product as a pale yellow solid (14.4 mg, 57 % yield). 1H-NMR (CDCb): 0.90 (t, 6H), 1.26 (bs, 56H), 1.60 (bs, 4H), 2.31 (t, 4H), 2.54 (m, 4H), 3.32 (m, 2H), 3.47 (m, 4H), 3.58 (m, 12H), 3.57 (d, 1H), 3.71 (t, 2H), 3.99 (bs, 4H), 4.10 (m, 1H), 4.36 (m, 1H), 5.07 (d, 1H), 5.15 (m, 1H), 7.23 (m, 2H), 7.29 (m, 2H), 7.36 (m, 3H), 7.58 (m, 1H), 7.64 (m, 1H), 11.3 (bs, 1H). HRMS TOF ES [Mr: mlz 1280.8057 (calculated for C71H1 15N3O1sP 1280.8066).

Reference： [1]Current Patent Assignee: ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI - WO2015/183876, 2015, A1 Location in patent: Paragraph 0136

33
[ 1069-79-0 ]
C₃₅H₃₈ClN₃O₁₀S₂ [ No CAS ]
C₇₂H₁₁₅ClN₃O₁₅PS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15.7 mg	In methanol; chloroform; water; N,N-dimethyl-formamide at 20℃; for 18h;

Reference： [1]Clear, Kasey J.; Virga, Katelyn; Gray, Lawrence; Smith, Bradley D. [Journal of Materials Chemistry C, 2016, vol. 4, # 14, p. 2925 - 2930]

34
[ 1069-79-0 ]
[ 955094-26-5 ]
C₅₅H₁₀₀N₃O₁₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylamine In N,N-dimethyl-formamide at 20℃; for 2h;

Reference： [1]Hu, Junjie; Liu, Fei; Ju, Huangxian [Angewandte Chemie - International Edition, 2016, vol. 55, # 23, p. 6667 - 6670][Angew. Chem., 2016, vol. 128, # 23, p. 6779 - 6782,4]

35
[ 108-30-5 ]
[ 1069-79-0 ]
C₄₅H₈₆NO₁₁P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform at 20℃; for 10h;
	With triethylamine at 40℃; for 24h;

Reference： [1]Du, Jiang-Bo; Cheng, Ying; Teng, Zeng-Hui; Huan, Meng-Lei; Liu, Miao; Cui, Han; Zhang, Bang-Le; Zhou, Si-Yuan [Molecular Pharmaceutics, 2016, vol. 13, # 5, p. 1711 - 1722]
[2]Current Patent Assignee: UNIVERSITY OF ULSTER - WO2021/198675, 2021, A1 Location in patent: Page/Page column 22

36
sialic acid [ No CAS ]
[ 1069-79-0 ]
C₅₂H₉₉N₂O₁₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: sialic acid; 1,2-distearoyl-sn-glycero-3-phosphoethanolamine With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine With triethylamine In chloroform; N,N-dimethyl-formamide at 20 - 70℃;	3 Example 3 Synthesis of Neu5Ac -DSPE At room temperature using 4 mL of DMF dissolved 40 mg Neu5Ac,Followed by the addition of 40 mg EDC · HCl and 24 mg NHS,At room temperature, the magnetic stirring was carried out for 2 h.Dissolve 20 mg of DSPE using 4 mL of chloroform,Add 26 μL of triethylamine,Heated to 40 ° C dissolved.The DSPE chloroform solution was gradually added to the DMF solution of Neu5Ac at room temperature,Stir for 2 h to obtain a mist suspension.The suspension was then slowly heated to a stirred condition70 ° C,After the system is clear to stop heating.The system into the room after the precipitation,Diluted with 3 times the volume of water after dialysis (dialysis bag cut molecular weight 1000 Da),The contents of the dialysis bag were lyophilized to obtain Neu5Ac -DSPE.

Reference： [1]Current Patent Assignee: SHENYANG PHARMACEUTICAL UNIVERSITY - CN104031097, 2016, B Location in patent: Paragraph 0067; 0068; 0069; 0070

37
[ 1069-79-0 ]
C₁₈H₂₁NO₁₁S [ No CAS ]
[ 15715-58-9 ]
C₅₉H₁₀₁N₂O₁₈PS*C₆H₁₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine; C₁₈H₂₁NO₁₁S With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane; chloroform; N,N-dimethyl-formamide at 20℃; for 15h; Stage #2: triethylamine carbonate In dichloromethane; water	Synthesis of 9 To a stirred solution of TBTU (0.033 g, 0.104 mmol) in dry DMF (0.6 mL) NMM (0.012 mL, 0.104 mmol) was added. The mixture was left strirring for 15 min at r.t than a solution of 7 (0.024 g, 0.052 mmol) in DMF (0.4 mL)was added. The reaction mixture was left stirring for 10 min than a solution of 8 in dry CH2Cl2:CHCl3 (3:1)was added. The mixture was warmed at 40 °C for 1 h then cooled to r.t and left stirred for 15 h. After this time the reaction mixture was diluted with CH2Cl2 (100 mL) and washed with H2O (1 × 10 mL), a 1 M solution of Triethylammonium bicarbonate (1 × 15 mL). The organic phase was dried over Na2SO4 and concentrated to dryness to give a crude which was purified by flash chromatographyon silica gel (AcOEt +0.1% NEt3 DCM: MeOH 5:1 + 0.1% NEt3 ) . Cationc exchange o f the triethylammonium salt of 9 with amberlite resin IR-120 Na+ (CHCl3: MeOH 2:1) gave 9 (0.028 g, 0.023 mmol,45%) as a glassy solid.

Reference： [1]Fallarini, Silvia; Brittoli, Alvaro; Fiore, Michele; Lombardi, Grazia; Renaudet, Olivier; Richichi, Barbara; Nativi, Cristina [Glycoconjugate Journal, 2017, vol. 34, # 4, p. 553 - 562]

38
[ 1069-79-0 ]
C₅₉H₁₀₀N₂O₁₈PS^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 4-methyl-morpholine / chloroform; N,N-dimethyl-formamide; dichloromethane / 15 h / 20 °C 2: Amberlite IR₁₂₀ Na+ form / chloroform; methanol

Reference： [1]Fallarini, Silvia; Brittoli, Alvaro; Fiore, Michele; Lombardi, Grazia; Renaudet, Olivier; Richichi, Barbara; Nativi, Cristina [Glycoconjugate Journal, 2017, vol. 34, # 4, p. 553 - 562]

39
[ 1069-79-0 ]
C₅₃H₉₅N₂O₁₅PS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 4-methyl-morpholine / chloroform; N,N-dimethyl-formamide; dichloromethane / 15 h / 20 °C 2: Amberlite IR₁₂₀ Na+ form / chloroform; methanol 3: potassium carbonate / chloroform; methanol / 1 h / 20 °C

Reference： [1]Fallarini, Silvia; Brittoli, Alvaro; Fiore, Michele; Lombardi, Grazia; Renaudet, Olivier; Richichi, Barbara; Nativi, Cristina [Glycoconjugate Journal, 2017, vol. 34, # 4, p. 553 - 562]

40
[ 1069-79-0 ]
[ 20769-85-1 ]
C₄₅H₈₇BrNO₉P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine With triethylamine In chloroform at 20℃; for 0.5h; Stage #2: 2-bromoisobutyric acid bromide In chloroform at 40℃;	1 Synthesis of DSPE-Br initiator: Triethylamine (0.3 ml, 2.35 mmol) was added to 30 ml of dried chloroform containing 0.88 gram (1.17 mmol) of distearoylphosphatidylethanolamine (DSPE), and the mixture was stirred at room temperature for 0.5 hour. 2-bromoisobutyryl bromide (0.115 ml, 1.17 mmol) was then injected into the solution. The mixture was then stirred overnight at 40 °C. The solution was washed with water three times, and a white power was obtained by removing the solvent using a rotary evaporator.

Reference： [1]Current Patent Assignee: WEIZMANN INSTITUTE OF SCIENCE - WO2017/109784, 2017, A1 Location in patent: Page/Page column 71-72

41
[ 1069-79-0 ]
p-SCN-Bn-DOTA [ No CAS ]
DOTA-Bn-DSPE [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In methanol; chloroform; water at 20 - 40℃; for 18h;	Synthesis of DOTA-Bn-DSPE 12 tmoles of p-SCN-Bn-DOTA was dissolved in 1 mL of chloroform:methanol:water (65:35:8) mixture and 22 tmoles of DSPE was dissolved in 1 mL of chloroform:methanol:water mixture. After mixing two solutions, 48 tmoles of triethylamine was added. The mixture was stirred at 40 °C for 2 h followed by stirring at room temperature for 16 h. The progress of reaction was monitored using silica gel coated TLC plates using in chloroform/methanol/water (65:35:1) as eluant and product formation was confirmed by mass spectroscopy.

Reference： [1]Current Patent Assignee: MEMORIAL SLOAN-KETTERING CANCER CENTER - WO2017/155948, 2017, A1 Location in patent: Paragraph 0090; 0156

42
[ 1069-79-0 ]
DBCO-NHS ester [ No CAS ]
C₆₃H₁₀₀N₃O₁₁P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72.1%	Stage #1: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine With triethylamine In chloroform at 20℃; for 1h; Stage #2: DBCO-NHS ester In chloroform	1 Preparation of Azabicyclooctynyl Distearoyl Phosphatidylethanolamine 220 mg of the aza-dibenzo cyclooctyne (ADIBO) was dissolved in 15 ml of chloroform, Add dropwise 0.2 ml of triethylamine, The reaction was carried out for 0.5 hour at room temperature. 105 mg of succinic anhydride, Reaction overnight at room temperature. After the reaction is completed, Dilute hydrochloric acid washed twice, Washed with saturated saline once, Dried over anhydrous sodium sulfate, The organic layer was concentrated. Dichloromethane / methanol column chromatography, A yellow oil (ADIBO-COOH, 224 mg, 74.7%) was obtained, 124 mg ADIBO-COOH And 37.9 mg of N-hydroxysuccinimide (NHS) were dissolved in 5 mL In chloroform, 60.3 mg dicyclohexylcarbodiimide (DCC) was added, Stir overnight at room temperature. After the reaction is completed, Suction filtration, The resulting full name (DCU) precipitate was removed, The filtrate spin dry. Dichloromethane / methanol column chromatography, To give a pale yellow solid (ADIBO -NHS, 101mg, 64.7%).74.8 mg of distearoyl phosphatidylethanolamine (DSPE) was dissolved in 4 mL of chloroform, 30.36 mg of triethylamine was added dropwise. After stirring at room temperature for 1 hour, 47.34 mg of ADIBO-NHS, Stir overnight. Dichloromethane / methanol column chromatography, A white solid (azabicyclooctynated distearoyl phosphatidylethanolamine, 72 mg, 72.1%).

Reference： [1]Current Patent Assignee: CHINA PHARMACEUTICAL UNIVERSITY - CN106478718, 2017, A Location in patent: Paragraph 0097; 0098; 0099; 0100

43
[ 1069-79-0 ]
[ 76823-03-5 ]
C₆₂H₉₂NO₁₄P [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 785 - 789
Angew. Chem.,2018,vol. 128,p. 793 - 797,5

44
[ 1069-79-0 ]
C₁₅H₁₂F₅NO₂S₃ [ No CAS ]
[ 121-44-8 ]
C₅₀H₉₃N₂O₉PS₃*C₆H₁₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine; triethylamine In dichloromethane at 20℃; Stage #2: C₁₅H₁₂F₅NO₂S₃ In dichloromethane at 0 - 20℃;	1 Example 1: Synthesis of (R)-1,2-Di-stearoyl-sn-glycero-3-phosphoethanolamine-ECT (DSPE-ECT) [269] This Example describes the synthesis of (i?)-l,2-Di-stearoyl-sn-glycero-3- phosphoethanolamine-ECT (DSPE-ECT), having the structure shown below. (0640) (0641) [270] (i?)-l,2-Di-stearoyl-sn-glycero-3-phosphoethanolamine (4.73 g, 6.32 mmol) was placed into a 500 mL round bottom flask and dissolved in anhydrous dichloromethane (50.0 mL) at RT. Triethylamine (2.20 mL, 15.8 mmol) was added to the mixture and the solution was cooled to 0 °C in an ice bath. In a separate 100 mL round bottom flask, ECT-pentafluorophenylacetate (4.05 g, 9.43 mmol) was dissolved in dichloromethane (20.0 mL) at RT and this mixture was added into the previously cooled DSPE solution via syringe over 10 min. The combined solution was allowed to warm to RT overnight and then diluted with dichloromethane (300 mL). The organic phase was washed with saturated sodium bicarbonate (2 x 50.0 mL) and brine (1 x 50.0 mL). The organic solution was dried over sodium sulfate overnight. The solid salts were filtered out and the organic solution was evaporated in vacuo. The yellow residue was dissolved in anhydrous diethyl ether and cooled to - 20 °C for 60 h. The yellow precipitate was filtered on a Buchner funnel and washed with cold ether, then immediately purified via silica gel chromatography using a gradient of dichloromethane and methanol (0 to 20%). The combined pure fractions were concentrated on the rotovap and the resulting yellow oil was dissolved in anhydrous diethyl ether then cooled to - 20 °C for 24 h. The yellow precipitate was filtered on a Buchner funnel, washed with ether and dried under high vacuum overnight. The pure product (yellow powder) was obtained as a triethylaminium salt (5.67 g, 5.70 mmol). Yield: 90% (Ti-NMR was taken in CDC13 on a Varian 400MHz).

Reference： [1]Current Patent Assignee: ARBUTUS BIOPHARMA CORP; ROIVANT SCIENCES GMBH - WO2018/126084, 2018, A1 Location in patent: Paragraph 269-270

45
C₅₉H₉₅N₂O₁₀P [ No CAS ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 25℃; for 1.5h;	10 Preparation of the compound of formula III (R=CH3(CH2)16): The compound of formula II (R=CH3(CH2)16, R1=-Fmoc) (0.50 g, 0.49 mmol) was dissolved in dichloromethane (10 mL).DBU (0.15 g, 0.98 mmol) was added at 25 ° C and reacted at 25 ° C for 1.5 h.AcOH (0.06 g, 1.08 mmol) was added, and after stirring for 5 min, the solvent was evaporated to dryness.The residual solvent was taken up with methanol and then beaten with ethyl acetate.The white solid compound (R=CH3(CH2)16) represented by formula III is 0.34 g,The yield was 94%.

Reference： [1]Current Patent Assignee: ANQING RUNKE BIOLOGICAL MEDICINE TECH - CN108727426, 2018, A Location in patent: Paragraph 0081; 0082; 0083; 0087; 0091

46
[ 1069-79-0 ]
(E)-2,5-dioxopyrrolidin-1-yl 1-(cyclooct-4-en-1-yloxy)-1-oxo-5,8,11,14-tetraoxa-2-azaheptadecan-17-oate [ No CAS ]
C₆₁H₁₁₅N₂O₁₅P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine In methanol; chloroform for 5h; Inert atmosphere;

Reference： [1]Hernández-Gil, Javier; Braga, Marta; Harriss, Bethany I.; Carroll, Laurence S.; Leow, Chee Hau; Tang, Meng-Xing; Aboagye, Eric O.; Long, Nicholas J. [Chemical Science, 2019, vol. 10, # 21, p. 5603 - 5615]

47
[ 1069-79-0 ]
trans-4-cycloocten-yl 2,5-dioxo-1-pyrrolidinyl ester carbonic acid [ No CAS ]
C₅₀H₉₄NO₁₀P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine In methanol; chloroform for 5h; Inert atmosphere;

Reference： [1]Hernández-Gil, Javier; Braga, Marta; Harriss, Bethany I.; Carroll, Laurence S.; Leow, Chee Hau; Tang, Meng-Xing; Aboagye, Eric O.; Long, Nicholas J. [Chemical Science, 2019, vol. 10, # 21, p. 5603 - 5615]

48
[ 1069-79-0 ]
[ 1338231-09-6 ]
C₅₃H₁₀₁N₄O₁₃P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine In methanol; chloroform for 5h; Inert atmosphere;

Reference： [1]Hernández-Gil, Javier; Braga, Marta; Harriss, Bethany I.; Carroll, Laurence S.; Leow, Chee Hau; Tang, Meng-Xing; Aboagye, Eric O.; Long, Nicholas J. [Chemical Science, 2019, vol. 10, # 21, p. 5603 - 5615]

49
[ 1069-79-0 ]
[ 170908-81-3 ]
C₅₇H₁₀₈N₅O₁₅P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine In methanol; chloroform for 5h; Inert atmosphere;

Reference： [1]Hernández-Gil, Javier; Braga, Marta; Harriss, Bethany I.; Carroll, Laurence S.; Leow, Chee Hau; Tang, Meng-Xing; Aboagye, Eric O.; Long, Nicholas J. [Chemical Science, 2019, vol. 10, # 21, p. 5603 - 5615]

50
[ 1069-79-0 ]
[ 4044-65-9 ]
C₄₉H₈₆N₃O₈PS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine In methanol; chloroform for 5h;

Reference： [1]Hernández-Gil, Javier; Braga, Marta; Harriss, Bethany I.; Carroll, Laurence S.; Leow, Chee Hau; Tang, Meng-Xing; Aboagye, Eric O.; Long, Nicholas J. [Chemical Science, 2019, vol. 10, # 21, p. 5603 - 5615]

51
[ 480436-46-2 ]
[ 1069-79-0 ]
1,2-distearoyl-sn-glycero-3-phosphoethanolamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine In methanol; chloroform at 20℃; Inert atmosphere;

Reference： [1]De Vrieze, Jana; Louage, Benoit; Deswarte, Kim; Zhong, Zifu; De Coen, Ruben; Van Herck, Simon; Nuhn, Lutz; Kaas Frich, Camilla; Zelikin, Alexander N.; Lienenklaus, Stefan; Sanders, Niek N.; Lambrecht, Bart N.; David, Sunil A.; De Geest, Bruno G. [Angewandte Chemie - International Edition, 2019, vol. 58, # 43, p. 15390 - 15395][Angew. Chem., 2019, vol. 131, # 43, p. 15535 - 15541,7]

52
C₁₄H₂₂Cl₃N₂O₈P [ No CAS ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: hydrogenchloride / methanol / 8 h / 18 °C 2: dmap; dicyclohexyl-carbodiimide / dichloromethane / 4.5 h / 18 °C / Cooling with ice 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 18 °C / Cooling with ice 4: acetic acid; zinc / tetrahydrofuran / 7 h / 18 °C

Reference： [1]Current Patent Assignee: EAST CHINA NORMAL UNIVERSITY; BIOCOMPOUNDS PHARMACEUTICAL - CN111285899, 2020, A

53
C₁₁H₁₈Cl₃N₂O₈P [ No CAS ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 4.5 h / 18 °C / Cooling with ice 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 18 °C / Cooling with ice 3: acetic acid; zinc / tetrahydrofuran / 7 h / 18 °C

Reference： [1]Current Patent Assignee: EAST CHINA NORMAL UNIVERSITY; BIOCOMPOUNDS PHARMACEUTICAL - CN111285899, 2020, A

54
C₄₄H₈₃Cl₃NO₁₀P [ No CAS ]
[ 1069-79-0 ]

Yield	Reaction Conditions	Operation in experiment
81.5%	With acetic acid; zinc In tetrahydrofuran at 18℃; for 7h;	17 Final product: Synthesis of Distearoylphosphatidylethanolamine 2g compound IV(R)(2-Hydroxy)(Trichloroethoxyformylaminoethoxy)(2,3-Distearoyloxypropyl)phosphoric esterAdd to 10mL THF, add 703mg zinc powderAnd 650 mg AcOH, the reaction temperature is 18° C., thin layer chromatography (TLC) monitors the progress of the reaction (dichloromethane: methanol = 9:1), and reacts for 7 hours.Suction filtration, evaporate to dryness, toluene is dried, and purified by column to obtain 1.32g of white waxy solid.The yield was 1.32/(2*748.08/923.47) = 81.5%.

Reference： [1]Current Patent Assignee: EAST CHINA NORMAL UNIVERSITY; BIOCOMPOUNDS PHARMACEUTICAL - CN111285899, 2020, A Location in patent: Paragraph 0101-0105

55
[ 1069-79-0 ]
C₁₂H₂₀N₂O₉Pt [ No CAS ]
C₅₃H₁₀₀N₃O₁₆PPt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride

Reference： [1]Feng, Liangzhu; Liu, Zhuang; Peng, Rui; Shen, Fengyun; Tao, Danlei; Xu, Jun; Zhu, Yujie [Biomaterials, 2020, vol. 255]

56
[ 1069-79-0 ]
C₉₀H₁₇₈O₄₈ [ No CAS ]
[ 121-44-8 ]
C₁₃₁H₂₅₇NO₅₅P^(1-)*C₆H₁₅N*Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₉₀H₁₇₈O₄₈ With 1,1'-carbonyldiimidazole In toluene at 90℃; Stage #2: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine; triethylamine In toluene at 90℃; Stage #3: With sodium chloride	1.2 Step 2-Synthesis of DSPE-PEG2-COOH PEG2DA was dissolved in toluene and warmed to 90° C. CDI was added portion-wise to control carbon dioxide evolution. Once all solids were dissolved and all bubbling has ceased, solid DSPE was added to the reaction mixture, followed by triethylamine. The mixture was stirred at 90° C. for 12-24 hours, at which time reaction completion was checked by TLC. Once complete, the reaction mixture was quenched with 5-10 mL of methanol and cooled to ambient temperature. Once cooled, the solution was diluted with chloroform and partitioned against 1 M aqueous hydrochloric acid to remove imidazole, followed by a brine wash. The mixture was neutralized with ammonium hydroxide prior to bulk solvent removal via rotary evaporation. The crude mixture was then sequentially chromatographed first with normal phase media (chloroform/methanol/ammonium hydroxide gradient) then with reverse phase media (methanol/water gradient) including a column wash with sodium chloride to achieve the sodium salt of DSPE-PEG2-COOH. FIGS. 9 and 10 show the 1H-NMR and 31P-NMR spectra of DSPE-PEG2-COOH respectively.

Reference： [1]Current Patent Assignee: APPLAUD MEDICAL - US10953023, 2021, B1 Location in patent: Page/Page column 53-56

57
[ 1069-79-0 ]
C₄₃H₇₃N₃O₂₂ [ No CAS ]
C₈₀H₁₅₀N₃O₂₇P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 72h; Inert atmosphere;	26 Maleimide-PEG2000-DSPE (15). DSPE (0.072 g, 0.096 mmol) and NHS-PEG2000-maleimide (0.200 g, 0.095 mmol) were dissolved in CHCl3 (15 mL) in a 50 mL round bottom, flask with stir bar and DIEA (0.062 g, 0.480) mmol was added via syringe. The flask was evacuated and flushed with nitrogen and stirred for 72 hours at ambient temperature. The volatiles were evaporated under reduced pressure and the residue purified by flash chromatography on silica using a gradient starting with 85:15 DCM: MeOH and increasing in polarity to 80:20 DCM:MeOH. Yield: 0.118 g (43%); TLC: Rf=0.48 (4:1 DCM:MeOH); 1H NMR (CDCl3): δ 0.84 (t 6H), 1.15-1.40 (m 64H), 2.24 (m 4H), 2.48 (t 2H) 2.99 (m 2H), 3.37-4.10 (m 180H), 3.80-3.96 (m 4H), 4.12 (m 2H), 4.34 (d 2H), 5.17 (m 1H), 6.27 (br 1H), 6.67 (s 1H), 7.38 (br 1H).

Reference： [1]Current Patent Assignee: PURDUE UNIVERSITY SYSTEM - US10989681, 2021, B2 Location in patent: Page/Page column 21-24

58
[ 1069-79-0 ]
[ 15026-17-2 ]
C₄₅H₈₆NO₁₁P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: succinic acid mono-tert-butyl ester With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: 1,2-distearoyl-sn-glycero-3-phosphoethanolamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 2h; Stage #3: With trifluoroacetic acid In N,N-dimethyl-formamide

Reference： [1]Jiang, Wei; Luo, Xingyu; Wei, Lulu; Yuan, Shanmei; Cai, Jianfeng; Jiang, Xiqun; Hu, Yong [Small, 2021, vol. 17, # 38]

59
[ 1069-79-0 ]
[ 189275-14-7 ]
C₅₇H₉₉FN₃O₁₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In chloroform at 20℃;

Reference： [1]Current Patent Assignee: UNIVERSITY OF ULSTER - WO2021/198675, 2021, A1 Location in patent: Page/Page column 24

60
[ 1069-79-0 ]
C₃₇H₄₂N₄O₉ [ No CAS ]
C₇₈H₁₂₂N₅O₁₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In chloroform at 45℃; for 24h;

Reference： [1]Current Patent Assignee: UNIVERSITY OF ULSTER - WO2021/198675, 2021, A1 Location in patent: Page/Page column 24

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CAS No. :	1069-79-0	MDL No. :	MFCD00036777
Formula :	C₄₁H₈₂NO₈P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LVNGJLRDBYCPGB-LDLOPFEMSA-N
M.W :	748.07	Pubchem ID :	447078
Synonyms :	1,2-Distearoyl-sn-glycero-3-phosphorylethanolamine;DSPE;1,2-Distearoyl-sn-glycero-3-Phosphoethanolamine 1,2-DSPE	Chemical Name :	(2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl distearate

Num. heavy atoms :	51
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.95
Num. rotatable bonds :	43
Num. H-bond acceptors :	9.0
Num. H-bond donors :	2.0
Molar Refractivity :	216.47
TPSA :	144.19 Å²

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-2.04 cm/s

Log Po/w (iLOGP) :	9.22
Log Po/w (XLOGP3) :	12.43
Log Po/w (WLOGP) :	12.06
Log Po/w (MLOGP) :	5.67
Log Po/w (SILICOS-IT) :	13.06
Consensus Log Po/w :	10.49

[ CAS No. 1069-79-0 ] {[proInfo.proName]}

Quality Control of [ 1069-79-0 ]

Related Doc. of [ 1069-79-0 ]

Product Details of [ 1069-79-0 ]

Calculated chemistry of [ 1069-79-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1069-79-0 ]

Application In Synthesis of [ 1069-79-0 ]

[ 1069-79-0 ] Synthesis Path-Downstream 1~60

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	2.0
Ghose :	None
Veber :	2.0
Egan :	2.0
Muegge :	3.0
Bioavailability Score :	0.17

Log S (ESOL) :	-9.47
Solubility :	0.000000253 mg/ml ; 0.0000000003 mol/l
Class :	Poorly soluble
Log S (Ali) :	-15.48
Solubility :	0.0 mg/ml ; 3.33e-16 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-12.7
Solubility :	0.0000000001 mg/ml ; 0.0 mol/l
Class :	Insoluble

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	7.81

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
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P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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