Name: 3386-32-1|Octadecyl 4-methylbenzenesulfonate|98%
Brand: Ambeed
SKU: A857408
Rating: 92 (40 reviews)

1
[ 3386-32-1 ]
[ 824-39-5 ]
[ 86996-83-0 ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 458

2
[ 3386-32-1 ]
[ 540-63-6 ]
[ 63347-81-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate at 120℃;

Reference： [1]Shirley; Reedy [Journal of the American Chemical Society, 1951, vol. 73, p. 4885]

3
[ 112-92-5 ]
[ 98-59-9 ]
[ 3386-32-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With aluminum dodecatungstophosphate at 20℃; for 0.483333h;
83%	With pyridine at 15℃; for 5h;
56%	With triethylamine In dichloromethane at 40℃; for 40h;

With pyridine

Reference： [1]Fazaeli, Razieh; Tangestaninejad, Shahram; Aliyan, Hamid [Canadian Journal of Chemistry, 2006, vol. 84, # 5, p. 812 - 818]
[2]Schueler, Fabian; Kerscher, Benjamin; Beckert, Fabian; Thomann, Ralf; Muelhaupt, Rolf [Angewandte Chemie - International Edition, 2013, vol. 52, # 1, p. 455 - 458][Angew. Chem., 2013, vol. 125, # 1, p. 473 - 476,4]
[3]Fedorova; Gromov; Eshcheulova; Zeiss; Moebius; Baryshnikova; Vereshchetin; Sergeeva; Zubov; Zaitsev; Alfimov [Russian Journal of Bioorganic Chemistry, 2000, vol. 26, # 9, p. 637 - 646]
[4]Sekera; Marvel [Journal of the American Chemical Society, 1933, vol. 55, p. 348] Marvel; Sekera [Organic syntheses. Collective volume, 1955, vol. III, p. 366] Barton, Derek H. R.; Jaszberenyi, Joseph Cs.; Theodorakis, Emmanouil A. [Tetrahedron, 1991, vol. 47, # 44, p. 9167 - 9178]
[5]Laughlin,R.G. [Journal of Organic Chemistry, 1962, vol. 27, p. 1005 - 1011]

4
[ 3386-32-1 ]
[ 112-27-6 ]
[ 4439-32-1 ]

Reference： [1]Wrigley,A.N. et al. [Journal of Organic Chemistry, 1960, vol. 25, p. 439 - 444]

5
[ 3386-32-1 ]
[ 100-79-8 ]
[ 16725-43-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydride In tetrahydrofuran
	With sodium hydride In N,N-dimethyl-formamide; Petroleum ether at 50℃;

Reference： [1]Haraldsson, Gudmundur G.; Thordarson, Pall; Halldorsson, Arnar; Kristinsson, Bjorn [Tetrahedron Asymmetry, 1999, vol. 10, # 19, p. 3671 - 3674]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

6
[ 3386-32-1 ]
[ 83526-68-5 ]
[ 83542-45-4 ]

Yield	Reaction Conditions	Operation in experiment
75.5%	With sodium hydride In N,N-dimethyl-formamide at 80℃;

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

7
[ 3386-32-1 ]
[ 22323-82-6 ]
[ 10585-86-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydride In N,N-dimethyl-formamide; Petroleum ether at 50℃; for 3h;

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

8
[ 3386-32-1 ]
butyl-octadecyl sulfide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With water

Reference： [1]Shirley; Reedy [Journal of the American Chemical Society, 1951, vol. 73, p. 4885]

9
[ 3386-32-1 ]
decyl-octadecyl sulfide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With water

Reference： [1]Shirley; Reedy [Journal of the American Chemical Society, 1951, vol. 73, p. 4885]

10
[ 3386-32-1 ]
[ 1844-09-3 ]

Yield	Reaction Conditions	Operation in experiment
	With water

Reference： [1]Shirley; Reedy [Journal of the American Chemical Society, 1951, vol. 73, p. 4885]

11
[ 112-92-5 ]
[ 104-15-4 ]
[ 3386-32-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	In dichloromethane for 10h; Heating;
51%	With tetrachlorosilane In dichloromethane for 4.5h; Heating;

Reference： [1]Das, Biswanath; Reddy, Vtukuri Saidi [Chemistry Letters, 2004, vol. 33, # 11, p. 1428 - 1429]
[2]Das, Biswanath; Reddy, V. Saidi; Reddy, M. Ravinder [Tetrahedron Letters, 2004, vol. 45, # 36, p. 6717 - 6719]

12
[ 3386-32-1 ]
[ 6129-13-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (i) K, benzene, (ii) /BRN= 2011780/ 2: NaOMe / methanol
	Multi-step reaction with 8 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h
	Multi-step reaction with 5 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 78 percent / pyridine / CH₂Cl₂ / 50 °C 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating

	Multi-step reaction with 5 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating
	Multi-step reaction with 2 steps 1: 1.) dibutyltin oxide / 1.) benzene, reflux, 1,5 h; 2.) 180-190 deg C, 30 min 2: H₂ / palladium on charcoal

Reference： [1]Karpova,N.B. et al. [Journal of Organic Chemistry USSR (English Translation), 1966, vol. 2, # 5, p. 791 - 793][Zhurnal Organicheskoi Khimii, 1966, vol. 2, # 5, p. 789 - 791]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[4]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[5]Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio; Kinoshita, Masayoshi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770]

13
[ 3386-32-1 ]
[ 83526-72-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 75 percent / NaH / tetrahydrofuran 2: aq. p-TsOH / tetrahydrofuran / Heating 3: lipase AK (Amano) / CHCl₃ / 72 h / 22 °C
	Multi-step reaction with 7 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: NaH / dimethylformamide / 80 °C 5: 1N HCl / dioxane / 90 °C 6: pyridine / CHCl₃ / Ambient temperature 7: H₂ / 5percent Pd/C / tetrahydrofuran / Ambient temperature
	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 9: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 10: Et₃N / 2 h / 80 °C

	Multi-step reaction with 8 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: toluene / 1 h / 80 °C 5: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 6: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 7: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 8: Et₃N / 2 h / 80 °C
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 72.5 percent / t-BuOK / tetrahydrofuran / Ambient temperature 5: dimethylformamide / 80 °C 6: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 7: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 8: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 9: Et₃N / 2 h / 80 °C

Reference： [1]Haraldsson, Gudmundur G.; Thordarson, Pall; Halldorsson, Arnar; Kristinsson, Bjorn [Tetrahedron Asymmetry, 1999, vol. 10, # 19, p. 3671 - 3674]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[4]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[5]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

14
[ 3386-32-1 ]
[ 82188-61-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) sodiumhydride / 1.) THF, oil, 30 min, room temp., 2.) 190-200 deg C 2: 61 percent / titanium tetrachloride / CH₂Cl₂ / 1 h / 0 °C
	Multi-step reaction with 2 steps 1: 1.) dibutyltin oxide / 1.) benzene, reflux, 1,5 h; 2.) 180-190 deg C, 30 min 2: 90 percent / H₂ / 10percent palladium on charcoal / ethanol; acetic acid / 45 °C / 760 Torr
	Multi-step reaction with 2 steps 1: 67 percent / sodium hydride / 1.) THF, 60 deg C; 2.) 190-200 deg C, 30 min 2: 90 percent / H₂ / 10percent palladium on charcoal / ethanol; acetic acid / 45 °C / 760 Torr

Reference： [1]Yamauchi, Kiyoshi; Hihara, Mitsuyoshi; Kinoshita, Masayoshi [Bulletin of the Chemical Society of Japan, 1987, vol. 60, p. 2169 - 2172]
[2]Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio; Kinoshita, Masayoshi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770]
[3]Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio; Kinoshita, Masayoshi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770]

15
[ 3386-32-1 ]
[ 74430-89-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 13 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h 9: 68.7 percent / pyridine / 72 h / Ambient temperature 10: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 11: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C 12: 79 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 13: 100 percent / H₂ / PdO / methanol; H₂O / 1 h / Ambient temperature
	Multi-step reaction with 11 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 9: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 10: 60 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 11: 61.8 percent / K₂CO₃ / methanol / 3 h / Ambient temperature
	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 78 percent / pyridine / CH₂Cl₂ / 50 °C 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature 7: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 8: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C 9: 79 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 10: 100 percent / H₂ / PdO / methanol; H₂O / 1 h / Ambient temperature

	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature 7: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 8: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C 9: 79 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 10: 100 percent / H₂ / PdO / methanol; H₂O / 1 h / Ambient temperature
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: toluene / 1 h / 80 °C 5: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 6: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 7: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 8: 60 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 9: 61.8 percent / K₂CO₃ / methanol / 3 h / Ambient temperature
	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 72.5 percent / t-BuOK / tetrahydrofuran / Ambient temperature 5: dimethylformamide / 80 °C 6: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 7: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 8: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 9: 60 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 10: 61.8 percent / K₂CO₃ / methanol / 3 h / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[4]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[5]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[6]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

16
[ 3386-32-1 ]
[ 38169-74-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h 9: 68.7 percent / pyridine / 72 h / Ambient temperature
	Multi-step reaction with 6 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 78 percent / pyridine / CH₂Cl₂ / 50 °C 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature
	Multi-step reaction with 6 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

17
[ 3386-32-1 ]
[ 83167-59-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 75.9 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 9: 93.8 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 0.25 h

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

18
[ 3386-32-1 ]
[ 75213-05-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 9: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature
	Multi-step reaction with 7 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: toluene / 1 h / 80 °C 5: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 6: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 7: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature
	Multi-step reaction with 8 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 72.5 percent / t-BuOK / tetrahydrofuran / Ambient temperature 5: dimethylformamide / 80 °C 6: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 7: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 8: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

19
[ 3386-32-1 ]
[ 74389-69-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 9: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 10: 60 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature
	Multi-step reaction with 8 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: toluene / 1 h / 80 °C 5: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 6: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 7: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 8: 60 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 72.5 percent / t-BuOK / tetrahydrofuran / Ambient temperature 5: dimethylformamide / 80 °C 6: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 7: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 8: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 9: 60 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

20
[ 3386-32-1 ]
[ 80707-93-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h 9: 68.7 percent / pyridine / 72 h / Ambient temperature 10: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 11: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C
	Multi-step reaction with 8 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 78 percent / pyridine / CH₂Cl₂ / 50 °C 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature 7: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 8: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C
	Multi-step reaction with 8 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature 7: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 8: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

21
[ 3386-32-1 ]
[ 80736-28-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: NaH / dimethylformamide / 80 °C 5: 1N HCl / dioxane / 90 °C 6: phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 7: H₂ / PdO / methanol; H₂O / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

22
[ 3386-32-1 ]
[ 80483-86-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 12 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h 9: 68.7 percent / pyridine / 72 h / Ambient temperature 10: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 11: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C 12: 79 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 78 percent / pyridine / CH₂Cl₂ / 50 °C 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature 7: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 8: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C 9: 79 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature 7: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 8: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C 9: 79 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

23
[ 3386-32-1 ]
(+)-Edelfosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 75.9 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 9: 93.8 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 0.25 h 10: 65 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

24
[ 3386-32-1 ]
[ 83526-63-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / Et₃N, Ac₂O, 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / -30 °C 9: 96.6 percent / H₂ / 5percent Pd/C / tetrahydrofuran

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

25
[ 3386-32-1 ]
[ 79637-90-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 9: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 10: phosphorus oxychloride, Et₃N / tetrahydrofuran / 0.67 h / 0 °C 11: 1N HCl / propan-2-ol
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: toluene / 1 h / 80 °C 5: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 6: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 7: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 8: phosphorus oxychloride, Et₃N / tetrahydrofuran / 0.67 h / 0 °C 9: 1N HCl / propan-2-ol
	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 72.5 percent / t-BuOK / tetrahydrofuran / Ambient temperature 5: dimethylformamide / 80 °C 6: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 7: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 8: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 9: phosphorus oxychloride, Et₃N / tetrahydrofuran / 0.67 h / 0 °C 10: 1N HCl / propan-2-ol

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

26
[ 3386-32-1 ]
Acetic acid (R)-1-octadecyloxymethyl-2-(2-oxo-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 9: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 10: phosphorus oxychloride, Et₃N / tetrahydrofuran / 0.67 h / 0 °C
	Multi-step reaction with 8 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: toluene / 1 h / 80 °C 5: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 6: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 7: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 8: phosphorus oxychloride, Et₃N / tetrahydrofuran / 0.67 h / 0 °C
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 72.5 percent / t-BuOK / tetrahydrofuran / Ambient temperature 5: dimethylformamide / 80 °C 6: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 7: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 8: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 9: phosphorus oxychloride, Et₃N / tetrahydrofuran / 0.67 h / 0 °C

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

27
[ 3386-32-1 ]
2-O-Acetyl-1-O-octadecyl-sn-glycero-3-(N-acetamidoaethyl)hydrogenphosphorsaeure [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 12 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 9: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 10: phosphorus oxychloride, Et₃N / tetrahydrofuran / 0.67 h / 0 °C 11: 1N HCl / propan-2-ol 12: 85.2 percent / pyridine / CHCl₃ / 8 h / Ambient temperature
	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: toluene / 1 h / 80 °C 5: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 6: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 7: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 8: phosphorus oxychloride, Et₃N / tetrahydrofuran / 0.67 h / 0 °C 9: 1N HCl / propan-2-ol 10: 85.2 percent / pyridine / CHCl₃ / 8 h / Ambient temperature
	Multi-step reaction with 11 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 72.5 percent / t-BuOK / tetrahydrofuran / Ambient temperature 5: dimethylformamide / 80 °C 6: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 7: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 8: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 9: phosphorus oxychloride, Et₃N / tetrahydrofuran / 0.67 h / 0 °C 10: 1N HCl / propan-2-ol 11: 85.2 percent / pyridine / CHCl₃ / 8 h / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

28
[ 3386-32-1 ]
2-O-Formyl-1-O-octadecyl-sn-glyceryl-3-phosphorylcholin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / Et₃N, Ac₂O, 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / -30 °C 9: 96.6 percent / H₂ / 5percent Pd/C / tetrahydrofuran 10: 51.5 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

29
[ 3386-32-1 ]
1-O-Octadecyl-2-O-propionyl-sn-glyceryl-3-phosphorylcholin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 14 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h 9: 68.7 percent / pyridine / 72 h / Ambient temperature 10: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 11: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C 12: 79 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 13: 100 percent / H₂ / PdO / methanol; H₂O / 1 h / Ambient temperature 14: 93.4 percent / 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature
	Multi-step reaction with 12 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 9: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 10: 60 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 11: 61.8 percent / K₂CO₃ / methanol / 3 h / Ambient temperature 12: 93.4 percent / 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature
	Multi-step reaction with 11 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 78 percent / pyridine / CH₂Cl₂ / 50 °C 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature 7: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 8: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C 9: 79 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 10: 100 percent / H₂ / PdO / methanol; H₂O / 1 h / Ambient temperature 11: 93.4 percent / 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature

	Multi-step reaction with 11 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature 7: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 8: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C 9: 79 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 10: 100 percent / H₂ / PdO / methanol; H₂O / 1 h / Ambient temperature 11: 93.4 percent / 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature
	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: toluene / 1 h / 80 °C 5: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 6: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 7: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 8: 60 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 9: 61.8 percent / K₂CO₃ / methanol / 3 h / Ambient temperature 10: 93.4 percent / 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature
	Multi-step reaction with 11 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 72.5 percent / t-BuOK / tetrahydrofuran / Ambient temperature 5: dimethylformamide / 80 °C 6: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 7: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 8: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 9: 60 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 10: 61.8 percent / K₂CO₃ / methanol / 3 h / Ambient temperature 11: 93.4 percent / 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[4]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[5]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[6]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

30
[ 3386-32-1 ]
2-O-Butyroyl-1-O-octadecyl-sn-glyceryl-3-phosphorylcholin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 14 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h 9: 68.7 percent / pyridine / 72 h / Ambient temperature 10: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 11: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C 12: 79 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 13: 100 percent / H₂ / PdO / methanol; H₂O / 1 h / Ambient temperature 14: 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature
	Multi-step reaction with 12 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 9: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 10: 60 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 11: 61.8 percent / K₂CO₃ / methanol / 3 h / Ambient temperature 12: 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature
	Multi-step reaction with 11 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 78 percent / pyridine / CH₂Cl₂ / 50 °C 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature 7: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 8: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C 9: 79 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 10: 100 percent / H₂ / PdO / methanol; H₂O / 1 h / Ambient temperature 11: 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature

	Multi-step reaction with 11 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature 7: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C 8: 88 percent / 1N HCl / dioxane / 1.5 h / 90 °C 9: 79 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 10: 100 percent / H₂ / PdO / methanol; H₂O / 1 h / Ambient temperature 11: 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature
	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: toluene / 1 h / 80 °C 5: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 6: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 7: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 8: 60 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 9: 61.8 percent / K₂CO₃ / methanol / 3 h / Ambient temperature 10: 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature
	Multi-step reaction with 11 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 72.5 percent / t-BuOK / tetrahydrofuran / Ambient temperature 5: dimethylformamide / 80 °C 6: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 7: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 8: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 9: 60 percent / phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature 10: 61.8 percent / K₂CO₃ / methanol / 3 h / Ambient temperature 11: 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[4]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[5]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[6]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

31
[ 3386-32-1 ]
[ 83526-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: NaH / dimethylformamide / 80 °C 5: 1N HCl / dioxane / 90 °C 6: pyridine / CHCl₃ / Ambient temperature 7: H₂ / 5percent Pd/C / tetrahydrofuran / Ambient temperature
	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 9: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 10: Et₃N / 2 h / 80 °C
	Multi-step reaction with 8 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: toluene / 1 h / 80 °C 5: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 6: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 7: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 8: Et₃N / 2 h / 80 °C

Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 72.5 percent / t-BuOK / tetrahydrofuran / Ambient temperature 5: dimethylformamide / 80 °C 6: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 7: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 8: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 9: Et₃N / 2 h / 80 °C

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[4]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

32
[ 3386-32-1 ]
[ 83526-55-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h 9: pyridine / CH₂Cl₂ / Ambient temperature
	Multi-step reaction with 6 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 78 percent / pyridine / CH₂Cl₂ / 50 °C 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: pyridine / CH₂Cl₂ / Ambient temperature
	Multi-step reaction with 6 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: pyridine / CH₂Cl₂ / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

33
[ 3386-32-1 ]
3-O-Acetyl-1-O-octadecyl-sn-glyceryl-2-phosphorylcholin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: NaH / dimethylformamide / 80 °C 5: 1N HCl / dioxane / 90 °C 6: pyridine / CHCl₃ / Ambient temperature 7: H₂ / 5percent Pd/C / tetrahydrofuran / Ambient temperature 8: phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature
	Multi-step reaction with 11 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 9: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 10: Et₃N / 2 h / 80 °C 11: phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: toluene / 1 h / 80 °C 5: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 6: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 7: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 8: Et₃N / 2 h / 80 °C 9: phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature

Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 72.5 percent / t-BuOK / tetrahydrofuran / Ambient temperature 5: dimethylformamide / 80 °C 6: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 7: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 8: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 9: Et₃N / 2 h / 80 °C 10: phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[4]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

34
[ 3386-32-1 ]
1-O-Acetyl-3-O-octadecyl-sn-glyceryl-2-phosphorylcholin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: NaH / dimethylformamide / 80 °C 5: 1N HCl / dioxane / 90 °C 6: pyridine / CHCl₃ / Ambient temperature 7: H₂ / 5percent Pd/C / tetrahydrofuran / Ambient temperature 8: phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature
	Multi-step reaction with 11 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: 100 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 9: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 10: Et₃N / 2 h / 80 °C 11: phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature
	Multi-step reaction with 9 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: toluene / 1 h / 80 °C 5: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 6: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 7: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 8: Et₃N / 2 h / 80 °C 9: phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature

Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 71 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 72.5 percent / t-BuOK / tetrahydrofuran / Ambient temperature 5: dimethylformamide / 80 °C 6: 100 percent / pyridine / 1.) RT; 2.) 80 deg C, 4 h 7: 82.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 8: 99.4 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h / Ambient temperature 9: Et₃N / 2 h / 80 °C 10: phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[4]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

35
[ 3386-32-1 ]
[ 80459-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 81 percent / pyridine / Ambient temperature 4: 99 percent / pyridine / CHCl₃ / Ambient temperature 5: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 6: t-BuOK / tetrahydrofuran / Ambient temperature 7: dimethylformamide / 80 °C 8: H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h 9: 68.7 percent / pyridine / 72 h / Ambient temperature 10: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C
	Multi-step reaction with 7 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: 78 percent / pyridine / CH₂Cl₂ / 50 °C 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature 7: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C
	Multi-step reaction with 7 steps 1: 87 percent / NaH / dimethylformamide; petroleum ether / 3 h / 50 °C 2: 81.5 percent / 1N HCl / dioxane / 1 h / Heating 3: pyridine / CH₂Cl₂ / 48 h / Ambient temperature 4: 81.5 percent / dimethylsulfoxide / 0.5 h / 140 °C 5: 68.5 percent / KOH / methanol; H₂O / 0.5 h / Heating 6: 68.7 percent / pyridine / 72 h / Ambient temperature 7: 98.6 percent / NaH / dimethylformamide / 2 h / 80 °C

Reference： [1]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[2]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]
[3]Hirth; Barner [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 1059 - 1084]

36
[ 3386-32-1 ]
[ 1069-97-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) dibutyltin oxide / 1.) benzene, reflux, 1,5 h; 2.) 180-190 deg C, 30 min 2: 90 percent / H₂ / 10percent palladium on charcoal / ethanol; acetic acid / 45 °C / 760 Torr 3: 60 percent / TPS-Cl / pyridine / 3 h / Ambient temperature 4: 84 percent / H₂ / 10percent palladium-on-charcoal / ethanol; ethyl acetate / 3 h / 40 - 50 °C
	Multi-step reaction with 4 steps 1: 67 percent / sodium hydride / 1.) THF, 60 deg C; 2.) 190-200 deg C, 30 min 2: 90 percent / H₂ / 10percent palladium on charcoal / ethanol; acetic acid / 45 °C / 760 Torr 3: 60 percent / TPS-Cl / pyridine / 3 h / Ambient temperature 4: 84 percent / H₂ / 10percent palladium-on-charcoal / ethanol; ethyl acetate / 3 h / 40 - 50 °C

Reference： [1]Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio; Kinoshita, Masayoshi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770]
[2]Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio; Kinoshita, Masayoshi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770]

37
[ 3386-32-1 ]
[ 106235-17-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) dibutyltin oxide / 1.) benzene, reflux, 1,5 h; 2.) 180-190 deg C, 30 min 2: 90 percent / H₂ / 10percent palladium on charcoal / ethanol; acetic acid / 45 °C / 760 Torr 3: 75 percent / TPS-Cl / pyridine / 3 h / Ambient temperature 4: 62 percent / H₂ / 10percent palladium-on-charcoal / ethanol; ethyl acetate
	Multi-step reaction with 4 steps 1: 67 percent / sodium hydride / 1.) THF, 60 deg C; 2.) 190-200 deg C, 30 min 2: 90 percent / H₂ / 10percent palladium on charcoal / ethanol; acetic acid / 45 °C / 760 Torr 3: 75 percent / TPS-Cl / pyridine / 3 h / Ambient temperature 4: 62 percent / H₂ / 10percent palladium-on-charcoal / ethanol; ethyl acetate

Reference： [1]Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio; Kinoshita, Masayoshi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770]
[2]Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio; Kinoshita, Masayoshi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770]

38
[ 3386-32-1 ]
[ 106235-12-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) dibutyltin oxide / 1.) benzene, reflux, 1,5 h; 2.) 180-190 deg C, 30 min 2: 90 percent / H₂ / 10percent palladium on charcoal / ethanol; acetic acid / 45 °C / 760 Torr 3: 60 percent / TPS-Cl / pyridine / 3 h / Ambient temperature
	Multi-step reaction with 3 steps 1: 67 percent / sodium hydride / 1.) THF, 60 deg C; 2.) 190-200 deg C, 30 min 2: 90 percent / H₂ / 10percent palladium on charcoal / ethanol; acetic acid / 45 °C / 760 Torr 3: 60 percent / TPS-Cl / pyridine / 3 h / Ambient temperature

Reference： [1]Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio; Kinoshita, Masayoshi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770]
[2]Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio; Kinoshita, Masayoshi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770]

39
[ 3386-32-1 ]
[ 106235-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) dibutyltin oxide / 1.) benzene, reflux, 1,5 h; 2.) 180-190 deg C, 30 min 2: 90 percent / H₂ / 10percent palladium on charcoal / ethanol; acetic acid / 45 °C / 760 Torr 3: 75 percent / TPS-Cl / pyridine / 3 h / Ambient temperature
	Multi-step reaction with 3 steps 1: 67 percent / sodium hydride / 1.) THF, 60 deg C; 2.) 190-200 deg C, 30 min 2: 90 percent / H₂ / 10percent palladium on charcoal / ethanol; acetic acid / 45 °C / 760 Torr 3: 75 percent / TPS-Cl / pyridine / 3 h / Ambient temperature

Reference： [1]Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio; Kinoshita, Masayoshi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770]
[2]Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio; Kinoshita, Masayoshi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770]

40
[ 3386-32-1 ]
[ 106235-13-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) dibutyltin oxide / 1.) benzene, reflux, 1,5 h; 2.) 180-190 deg C, 30 min 2: 90 percent / H₂ / 10percent palladium on charcoal / ethanol; acetic acid / 45 °C / 760 Torr 3: 55 percent / TPS-Cl / pyridine / 3 h / Ambient temperature
	Multi-step reaction with 3 steps 1: 67 percent / sodium hydride / 1.) THF, 60 deg C; 2.) 190-200 deg C, 30 min 2: 90 percent / H₂ / 10percent palladium on charcoal / ethanol; acetic acid / 45 °C / 760 Torr 3: 55 percent / TPS-Cl / pyridine / 3 h / Ambient temperature

Reference： [1]Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio; Kinoshita, Masayoshi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770]
[2]Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio; Kinoshita, Masayoshi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770]

41
[ 3386-32-1 ]
[ 4105-89-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. NaOH solution 2: SnCl₂; acetic acid

Reference： [1]Shirley; Reedy [Journal of the American Chemical Society, 1951, vol. 73, p. 458]

42
[ 3386-32-1 ]
[ 42714-86-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: water 2: potassium permanganate; acetic acid

Reference： [1]Shirley; Reedy [Journal of the American Chemical Society, 1951, vol. 73, p. 4885]

43
[ 3386-32-1 ]
[ 24244-61-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. NaOH solution 2: potassium permanganate; acetic acid

Reference： [1]Shirley; Reedy [Journal of the American Chemical Society, 1951, vol. 73, p. 4885]

44
[ 3386-32-1 ]
4-octadecylmercapto-aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. NaOH solution 2: SnCl₂; acetic acid

Reference： [1]Shirley; Reedy [Journal of the American Chemical Society, 1951, vol. 73, p. 4885]

45
[ 3386-32-1 ]
4-(octadecane-1-sulfonyl)-aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: aq. NaOH solution 2: potassium permanganate; acetic acid 3: SnCl₂; acetic acid

Reference： [1]Shirley; Reedy [Journal of the American Chemical Society, 1951, vol. 73, p. 4885]

46
[ 3386-32-1 ]
[ 860711-78-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. NaOH solution 2: potassium permanganate; acetic acid

Reference： [1]Shirley; Reedy [Journal of the American Chemical Society, 1951, vol. 73, p. 4885]

47
[ 120987-21-5 ]
[ 3386-32-1 ]
(+)-p-chlorobenzyl 4'-(1-octadecyloxyethyl)-4-biphenylcarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In <i>N</i>-methyl-acetamide	17 EXAMPLE 17 3.65 g (10 mmol) of V-17 was dissolved in 30 mo of dimethylformamide and cooled to 10° C. To this solution was added 0.48 g (12 mmol) of sodium hydride, followed by standing at 30°-35° C. for one hour. Then the mixture was further added with 5.1 g (12 mmol) of n-octadecyl tosylate at 20°-25° C. and reacted at 40° C. for 5 hours. The reaction mixture was poured into ice-water and extracted with 50 ml of ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure. The residue was purified by column chromatography to obtain 5.07 g (82% yield) of (+)-p-chlorobenzyl 4'-(1-octadecyloxyethyl)-4-biphenylcarboxylate (VII-17). [α]D20 =+21.1° (c=0.98, CHCl3), nD20 =1.5314.

Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US5019298, 1991, A

48
[ 3386-32-1 ]
[ 100565-84-2 ]

Yield	Reaction Conditions	Operation in experiment
65%		6 EXAMPLE 6: EXAMPLE 6: 2-Methyl-3-n-octadecyloxy-7-ethoxycarbonylmethylthio-pyrazolo[4,3-d]pyrimidine. STR49 Starting compound: n-octadecyl p-toluenesulfonate. Yield: 65%. Melting point: 49.5°-50.5° C. (as recrystallized from hexane). pmr (CDC13) δppm: 0.7-2.0 (m, 38H), 3.95 (s, 3H), 4.12 (s, 2H), 4.21 (q, 2H, J=7.5 Hz), 4.87 2H, J=6.5 Hz), 8.47 (s, 1H).

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US4654348, 1987, A

49
[ 3386-32-1 ]
[ 100566-53-8 ]

Yield	Reaction Conditions	Operation in experiment
57%		67 EXAMPLE 67: EXAMPLE 67: 2-t-Butyl-3-n-octadecyloxy-7-ethoxycarbonylmethylthio-pyrazolo[4,3-d]pyrimidine STR111 Starting compound: n-octadecyl p-toluenesulfonate. Yield 57%. Melting point: 33°-37° C. (Oily substance solidifies when left to stand still.). pmr (CDCl3) δppm: 0.88 (t, 3H, J=6 Hz), 1.21-1.92 (m, 35H), 1.71 (s, 9H), 4.13 (s, 2H), 4.23 (q, 2H, J=7 Hz), 4.91 (t, 2H, J=6 Hz), 8.45 (s, 1H).

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US4654348, 1987, A

50
[ 3386-32-1 ]
[ 173537-40-1 ]
[ 1451057-79-6 ]

Yield	Reaction Conditions	Operation in experiment
25%	With potassium carbonate In acetonitrile Reflux;

Reference： [1]Bussolati, Rocco; Carrieri, Pasquale; Secchi, Andrea; Arduini, Arturo; Credi, Alberto; Semeraro, Monica; Venturi, Margherita; Silvi, Serena; Velluto, Diana; Zappacosta, Romina; Fontana, Antonella [Organic and Biomolecular Chemistry, 2013, vol. 11, # 35, p. 5944 - 5953]

51
[ 553-26-4 ]
[ 3386-32-1 ]
1-octadecy-[4,4’-bipyridin]-1-ium 4-methylbenzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In acetonitrile for 24h; Reflux;	Salt 11. In a 100 mL round-bottomed flask, 1-octadecyl tosylate 10 (1 g, 2.4 mmol) and 4,4'-dipyridyl (1.1 g, 7.1 mmol) were dissolved in CH3CN (50 mL) and the solution was refluxed for 24 h. Then the solvent was evaporated at reduced pressure and the oily residue obtained was triturated with EtOAc (320 mL) until of 11 precipitated as a white solid recovered by suction filtration (1 g,64%). m.p. = 97-99 °C; 1H NMR (CD3OD, 400 MHz) δ = 9.12 (d, 2H,J = 6.0 Hz), 8.85 (d, 2H, J = 6.8 Hz), 8.52 (d, 2H, J = 5.6 Hz), 7.99 (d, 2H,J = 6.4 Hz), 7.72 (d, 2H, J = 7.6 Hz), 7.24 (d, 2H, J = 8.0 Hz), 4.68 (t, 2H,J = 7.6 Hz), 2.37 (s, 3H), 2.18 (t, 2H, J = 6.8 Hz), 1.4-1.3 (m, 30H), 0.92(t, 3H, J = 6.0 Hz); 13C NMR (CD3OD,100 MHz) δ = 153.9, 150.4,142.3,142.2, 140.2, 128.4, 125.7, 125.6, 122.1, 61.4, 31.7, 31.1, 29.4, 29.3,29.2, 29.1, 28.7, 25.8, 22.3, 19.9, 13.0; MS (ESI): m/z: 409.3 (100)[MTsO]+, 410.3 (33) [MTsO]+.
64%	In acetonitrile for 24h; Reflux;
64%	In acetonitrile for 24h; Reflux;

Reference： [1]Orlandini, Guido; Groppi, Jessica; Secchi, Andrea; Arduini, Arturo; Kilburn, Jeremy D. [Electrochimica Acta, 2017, vol. 227, p. 391 - 400]
[2]Orlandini, Guido; Ragazzon, Giulio; Zanichelli, Valeria; Secchi, Andrea; Silvi, Serena; Venturi, Margherita; Arduini, Arturo; Credi, Alberto [Chemical Communications, 2017, vol. 53, # 45, p. 6172 - 6174]
[3]Zanichelli, Valeria; Ragazzon, Giulio; Orlandini, Guido; Venturi, Margherita; Credi, Alberto; Silvi, Serena; Arduini, Arturo; Secchi, Andrea [Organic and Biomolecular Chemistry, 2017, vol. 15, # 32, p. 6753 - 6763]

52
[ 3386-32-1 ]
[ 480-44-4 ]
C₅₂H₈₄O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.28%	With sodium carbonate In benzene at 20 - 130℃; for 8h;	1 Example 1 Dissolve 23g acacetin in 100mL anhydrous benzene solution, add 69.1g octadecyl p-toluenesulfonate at room temperature, stir to dissolve, heat up to 130, add sodium carbonate, react for 8h, detect by thin layer chromatography After the reaction is complete, cool to room temperature, filter, extract the filtrate with ethyl acetate, wash the organic phase with 5% hydrochloric acid solution, saturated brine, and water successively, dry and concentrate to obtain a concentrated solution. Add 6 times the weight of silica gel to the concentrated solution. Mix the sample, dry the mixed sample silica gel at 3040, elution chromatography on a silica gel column, the eluent is a mixture of petroleum ether and ethyl acetate, the volume ratio of the two is 6:1, collect the column chromatography solution, 45 The extract is concentrated to dryness, and the extract is further purified by high performance liquid chromatography. The conditions of high performance liquid chromatography are as follows: the chromatographic column is an octadecylsilane bonded silica gel column, and its model is Agilent XDB-C18, 250 *4.6um, 5um, the mobile phase is a methanol solution with a volume ratio of methanol to water of 80:25, the mobile phase flow rate is 2.0mL/min, the injection volume is 15uL, the UV detection wavelength is 285nm, and the column temperature is room temperature. According to the UV detection results, Collect the eluent for 25 to 26 minutes, and concentrate the eluent under reduced pressure to obtain the acacetin derivative. The yield was 80.28%.

Reference： [1]- CN112876442, 2021, A Location in patent: Paragraph 0019-0022

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CAS No. :	3386-32-1	MDL No. :	MFCD00191588
Formula :	C₂₅H₄₄O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IZSBVVGANRHKEE-UHFFFAOYSA-N
M.W :	424.68	Pubchem ID :	229551
Synonyms :

Num. heavy atoms :	29
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.76
Num. rotatable bonds :	19
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	127.31
TPSA :	51.75 Å²

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-1.59 cm/s

Log Po/w (iLOGP) :	6.06
Log Po/w (XLOGP3) :	10.28
Log Po/w (WLOGP) :	9.04
Log Po/w (MLOGP) :	6.03
Log Po/w (SILICOS-IT) :	7.96
Consensus Log Po/w :	7.87

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Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	-7.85
Solubility :	0.00000602 mg/ml ; 0.0000000142 mol/l
Class :	Poorly soluble
Log S (Ali) :	-11.31
Solubility :	0.0000000021 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-9.62
Solubility :	0.000000102 mg/ml ; 0.0000000002 mol/l
Class :	Poorly soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	4.14

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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[ CAS No. 3386-32-1 ] {[proInfo.proName]}

Quality Control of [ 3386-32-1 ]

Related Doc. of [ 3386-32-1 ]

Product Details of [ 3386-32-1 ]

Calculated chemistry of [ 3386-32-1 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3386-32-1 ]

Application In Synthesis of [ 3386-32-1 ]

[ 3386-32-1 ] Synthesis Path-Downstream 1~52

Related Functional Groups of [ 3386-32-1 ]

Aryls

Sulfonates

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 3386-32-1 ]