Name: 226393-33-5|(2R,5R)-1-Hydroxy-2,5-diphenylphospholane 1-oxide|98%
Brand: Ambeed
SKU: A1326423
Price: 31.0 USD
Availability: InStock
Rating: 93 (25 reviews)

1
[ 226393-33-5 ]
(2R,5R)-1-Chloro-2,5-diphenyl-phospholane 1-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride In tetrahydrofuran Yield given;

Reference： [1]Guillen, Frederic; Fiaud, Jean-Claude [Tetrahedron Letters, 1999, vol. 40, # 15, p. 2939 - 2942]

2
(+/-)-1-(N,N-dimethylamino)-1-r-oxo-2-c,5-t-diphenylphospholane [ No CAS ]
[ 226393-33-5 ]
[ 474049-73-5 ]

Yield	Reaction Conditions	Operation in experiment
40%	With hydrogenchloride In methanol
1: 1.18 g 2: 1.15 g	With hydrogenchloride In ethanol; water at 20℃; for 16h;

Reference： [1]Guillen, Frederic; Fiaud, Jean-Claude [Tetrahedron Letters, 1999, vol. 40, # 15, p. 2939 - 2942]
[2]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]

3
[ 908094-01-9 ]
[ 226393-33-5 ]
(R,R)-(+)-1-methoxy-1-r-oxo-2-c,5-t-diphenylphospholane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	In diethyl ether; dichloromethane at 20℃;

Reference： [1]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]

4
[ 226393-33-5 ]
[ 226393-40-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With oxalyl dichloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
	With oxalyl dichloride In tetrahydrofuran for 2h;
	With oxalyl dichloride In tetrahydrofuran

	With oxalyl dichloride In tetrahydrofuran at 0 - 20℃; for 2.08333h;
	With oxalyl dichloride In tetrahydrofuran Inert atmosphere; Autoclave;

Reference： [1]Location in patent: experimental part Goudriaan, P. Elsbeth; Jang, Xiao-Bin; Kuil, Mark; Lemmens, Renske; Van Leeuwen, Piet W. N. M.; Reek, Joost N. H. [European Journal of Organic Chemistry, 2008, # 36, p. 6079 - 6092]
[2]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]
[3]Rivard, Michael; Guillen, Frederic; Fiaud, Jean-Claude; Aroulanda, Christie; Lesot, Philippe [Tetrahedron Asymmetry, 2003, vol. 14, # 9, p. 1141 - 1152]
[4]Birkholz, Mandy-Nicole; Dubrovina, Natalia V.; Jiao, Haijun; Michalik, Dirk; Holz, Jens; Paciello, Rocco; Breit, Bernhard; Boerner, Armin [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5896 - 5907]
[5]Location in patent: scheme or table Dobrota, Cristian; Duraud, Amelie; Toffano, Martial; Fiaud, Jean-Claude [European Journal of Organic Chemistry, 2008, # 14, p. 2439 - 2445]

5
[ 226393-33-5 ]
(R,R)-2,5-trans-diphenylphospholane-borane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: (R,R)-(+)-1-hydroxy-1-oxo-2,5-trans-diphenylphospholane With phenylsilane In toluene at 110℃; for 16h; Stage #2: With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 16h;
83%	Stage #1: (R,R)-(+)-1-hydroxy-1-oxo-2,5-trans-diphenylphospholane With phenylsilane In toluene Stage #2: With dimethylsulfide borane complex Further stages.;
	Multi-step reaction with 2 steps 1.1: (COCl)2 / tetrahydrofuran 2.1: LiAlH₄ / diethyl ether 2.2: 50 percent / BH₃*Me₂S / diethyl ether / 2 h / 20 °C

Reference： [1]Pilkington, Christopher J.; Zanotti-Gerosa, Antonio [Organic Letters, 2003, vol. 5, # 8, p. 1273 - 1275]
[2]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]
[3]Rivard, Michael; Guillen, Frederic; Fiaud, Jean-Claude; Aroulanda, Christie; Lesot, Philippe [Tetrahedron Asymmetry, 2003, vol. 14, # 9, p. 1141 - 1152]

6
[ 226393-33-5 ]
(2R,5R)-2,5-diphenylphospholane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With phenylsilane In toluene at 100℃; for 4h;	1.i (RJi)-I -Hydroxy- l-oxo-2,5-.rα/ts-diphenylphospholane (40.1 g, 147.3 mmol; prepared according the method of Guillen, F et al. Tetrahedron 2002, 58, 5895) was suspended in toluene (450 ml). The mixture was degassed by evacuation and filling with nitrogen (*5) and then heated in an oil bath at 120 0C (internal temperature 100 0C). Phenylsilane (36.3 ml, 294.5 mmol) was added in portions over 2h. The solution was heated for a further 2h and then cooled to 5 0C. Borane dimethyl sulfide complex (94%, 15 ml, 147.3 mmol) was added over 5 minutes. The mixture was allowed to warm to room temperature and stirred overnight. The solution was filtered through a pad of silica (10Og), eluting with toluene (600 ml). Concentrated under reduced pressure and crystallized from toluene/heptane (1 :4, 150 ml). The solid was filtered and washed with toluene/heptane (1 :4, 50 ml). Dried under vacuum to give the title compound (31.22 g, 83%).1H NMR (400 MHz, CDCl3) δ ppm 7.2-7.4 (10 H, m), 4.82 (1 H, dq, Jm 361 Hz, JHH 11Hz), 3.95 (1 H, m), 3.52 (1 H, m), 2.55-2.65 (2 H, m), 2.15-2.25 (2 H, m) and 0.1-0.9 (3 H, br q, BH3).13C NMR (100 MHz, CDCl3) 6 ppm 138.1 (d, J 5 Hz), 136.9, 129.4, 129.1, 129.0, 128.9,128.2, 127.7, 44.9 (d, J33 Hz), 41.0 (d, 729 Hz), 35.0 (d, JA Hz) and 34.3.31P NMR (162 MHz, CDCl3) δppm 30.1.
	With phenylsilane In toluene at 110℃; for 19h; Inert atmosphere;

Reference： [1]Current Patent Assignee: DOW INC; DR REDDY'S LABORATORIES LIMITED - WO2007/123957, 2007, A2 Location in patent: Page/Page column 8
[2]Lloret Fillol, Julio; Kruckenberg, Achim; Scherl, Peter; Wadepohl, Hubert; Gade, Lutz H. [Chemistry - A European Journal, 2011, vol. 17, # 50, p. 14047 - 14062]

7
(+/-)-1-hydroxy-1-oxo-2,5-trans-diphenylphospholane [ No CAS ]
[ 226393-33-5 ]
[ 474049-73-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 28% 2: 24%	Stage #1: (+/-)-1-hydroxy-1-oxo-2,5-trans-diphenylphospholane With quinine In methanol Reflux; Resolution of racemate; Stage #2: With sodium hydroxide In dichloromethane; water for 0.166667h; Further stages;
	With Quinine

Reference： [1]Busacca, Carl A.; Farber, Elisa; Deyoung, Jay; Campbell, Scot; Gonnella, Nina C.; Grinberg, Nelu; Haddad, Nizar; Lee, Heewon; Ma, Shengli; Reeves, Diana; Shen, Sherry; Senanayake, Chris H. [Organic Letters, 2009, vol. 11, # 24, p. 5594 - 5597]
[2]Birkholz, Mandy-Nicole; Dubrovina, Natalia V.; Jiao, Haijun; Michalik, Dirk; Holz, Jens; Paciello, Rocco; Breit, Bernhard; Boerner, Armin [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5896 - 5907]

8
[ 538-81-8 ]
[ 226393-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 83 percent / AlCl₃ / H₂O 2.1: 99 percent / H₂ / Pd/C / 37503.8 Torr 3.1: MeONa / methanol 3.2: 94 percent / aq. HCl 4.1: quinine
	Multi-step reaction with 5 steps 1: AlCl₃ / CH₂Cl₂ / 16 h / 0 °C 2: 16.5 g / NaHCO₃; EDTA / CH₂Cl₂ / 4 h / 0 °C 3: 92 percent / hydrogen / 10 percent Pd/C / methanol / 16 h / 37503 Torr 4: 95 percent / NaOMe / methanol / 1.25 h / 20 °C 5: 1.15 g / HCl / H₂O; ethanol / 16 h / 20 °C
	Multi-step reaction with 5 steps 1: AlCl₃ / CH₂Cl₂ / 16 h / 0 °C 2: 16.5 g / NaHCO₃; EDTA / CH₂Cl₂ / 4 h / 0 °C 3: 92 percent / hydrogen / 10 percent Pd/C / methanol / 16 h / 37503 Torr 4: 61 percent / MeLi / tetrahydrofuran / 16 h / 20 °C 5: 1.15 g / HCl / H₂O; ethanol / 16 h / 20 °C

Reference： [1]Birkholz, Mandy-Nicole; Dubrovina, Natalia V.; Jiao, Haijun; Michalik, Dirk; Holz, Jens; Paciello, Rocco; Breit, Bernhard; Boerner, Armin [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5896 - 5907]
[2]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]
[3]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]

9
[ 226393-33-5 ]
[ 949160-19-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: oxalyl chloride / tetrahydrofuran / 2.08 h / 0 - 20 °C 2.1: LiAlH₄ / tetrahydrofuran / 1 h / -20 °C 2.2: air / propan-2-ol / 5 h 3.1: iPr₂NEt; 1,3-bis(diphenylphosphanyl)propane / Pd(trans,trans-dibenzylideneacetone)2 / dimethylformamide / 18 h / 105 °C

Reference： [1]Birkholz, Mandy-Nicole; Dubrovina, Natalia V.; Jiao, Haijun; Michalik, Dirk; Holz, Jens; Paciello, Rocco; Breit, Bernhard; Boerner, Armin [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5896 - 5907]

10
[ 226393-33-5 ]
C₂₅H₂₉BNOP [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: oxalyl chloride / tetrahydrofuran / 2.08 h / 0 - 20 °C 2.1: LiAlH₄ / tetrahydrofuran / 1 h / -20 °C 2.2: air / propan-2-ol / 5 h 3.1: iPr₂NEt; 1,3-bis(diphenylphosphanyl)propane / Pd(trans,trans-dibenzylideneacetone)2 / dimethylformamide / 18 h / 105 °C 4.1: methyl triflate / 1,2-dimethoxy-ethane / 2 h 4.2: LiAlH₄ / 1,2-dimethoxy-ethane / 1.5 h / 20 °C 4.3: 60 percent / BH₃*SMe₂ / toluene / 15 h

Reference： [1]Birkholz, Mandy-Nicole; Dubrovina, Natalia V.; Jiao, Haijun; Michalik, Dirk; Holz, Jens; Paciello, Rocco; Breit, Bernhard; Boerner, Armin [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5896 - 5907]

11
[ 226393-33-5 ]
[ 949160-25-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: oxalyl chloride / tetrahydrofuran / 2.08 h / 0 - 20 °C 2.1: LiAlH₄ / tetrahydrofuran / 1 h / -20 °C 2.2: air / propan-2-ol / 5 h 3.1: iPr₂NEt; 1,3-bis(diphenylphosphanyl)propane / Pd(trans,trans-dibenzylideneacetone)2 / dimethylformamide / 18 h / 105 °C 4.1: methyl triflate / 1,2-dimethoxy-ethane / 2 h 4.2: LiAlH₄ / 1,2-dimethoxy-ethane / 1.5 h / 20 °C 4.3: 60 percent / BH₃*SMe₂ / toluene / 15 h 5.1: 74 percent / DABCO / tetrahydrofuran / 2 h / Heating
	Multi-step reaction with 4 steps 1.1: oxalyl chloride / tetrahydrofuran / 2.08 h / 0 - 20 °C 2.1: LiAlH₄ / tetrahydrofuran / 1 h / -20 °C 2.2: air / propan-2-ol / 5 h 3.1: iPr₂NEt; 1,3-bis(diphenylphosphanyl)propane / Pd(trans,trans-dibenzylideneacetone)2 / dimethylformamide / 18 h / 105 °C 4.1: HSiCl₃; NEt₃ / acetonitrile / 24 h / Heating

Reference： [1]Birkholz, Mandy-Nicole; Dubrovina, Natalia V.; Jiao, Haijun; Michalik, Dirk; Holz, Jens; Paciello, Rocco; Breit, Bernhard; Boerner, Armin [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5896 - 5907]
[2]Birkholz, Mandy-Nicole; Dubrovina, Natalia V.; Jiao, Haijun; Michalik, Dirk; Holz, Jens; Paciello, Rocco; Breit, Bernhard; Boerner, Armin [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5896 - 5907]

12
[ 226393-33-5 ]
(2R,5R)-(+)-(1H-pyrid-6-on-2-yl)-2,5-diphenylphospholane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: oxalyl chloride / tetrahydrofuran / 2.08 h / 0 - 20 °C 2.1: LiAlH₄ / tetrahydrofuran / 1 h / -20 °C 2.2: air / propan-2-ol / 5 h 3.1: iPr₂NEt; 1,3-bis(diphenylphosphanyl)propane / Pd(trans,trans-dibenzylideneacetone)2 / dimethylformamide / 18 h / 105 °C 4.1: methyl triflate / 1,2-dimethoxy-ethane / 2 h 4.2: LiAlH₄ / 1,2-dimethoxy-ethane / 1.5 h / 20 °C 4.3: 60 percent / BH₃*SMe₂ / toluene / 15 h 5.1: 74 percent / DABCO / tetrahydrofuran / 2 h / Heating 6.1: conc. formic acid / 3 h
	Multi-step reaction with 5 steps 1.1: oxalyl chloride / tetrahydrofuran / 2.08 h / 0 - 20 °C 2.1: LiAlH₄ / tetrahydrofuran / 1 h / -20 °C 2.2: air / propan-2-ol / 5 h 3.1: iPr₂NEt; 1,3-bis(diphenylphosphanyl)propane / Pd(trans,trans-dibenzylideneacetone)2 / dimethylformamide / 18 h / 105 °C 4.1: HSiCl₃; NEt₃ / acetonitrile / 24 h / Heating 5.1: conc. formic acid / 3 h

Reference： [1]Birkholz, Mandy-Nicole; Dubrovina, Natalia V.; Jiao, Haijun; Michalik, Dirk; Holz, Jens; Paciello, Rocco; Breit, Bernhard; Boerner, Armin [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5896 - 5907]
[2]Birkholz, Mandy-Nicole; Dubrovina, Natalia V.; Jiao, Haijun; Michalik, Dirk; Holz, Jens; Paciello, Rocco; Breit, Bernhard; Boerner, Armin [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5896 - 5907]

13
[ 226393-33-5 ]
[ 226417-49-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: oxalyl chloride / tetrahydrofuran / 2.08 h / 0 - 20 °C 2.1: LiAlH₄ / tetrahydrofuran / 1 h / -20 °C 2.2: air / propan-2-ol / 5 h
	Multi-step reaction with 2 steps 1.1: oxalyl chloride / tetrahydrofuran / 2 h 2.1: LiAlH₄ / diethyl ether 2.2: 53 percent / H₂O / diethyl ether

Reference： [1]Birkholz, Mandy-Nicole; Dubrovina, Natalia V.; Jiao, Haijun; Michalik, Dirk; Holz, Jens; Paciello, Rocco; Breit, Bernhard; Boerner, Armin [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5896 - 5907]
[2]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]

14
[ 226393-31-3 ]
[ 226393-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 99 percent / H₂ / Pd/C / 37503.8 Torr 2.1: MeONa / methanol 2.2: 94 percent / aq. HCl 3.1: quinine
	Multi-step reaction with 3 steps 1: 92 percent / hydrogen / 10 percent Pd/C / methanol / 16 h / 37503 Torr 2: 95 percent / NaOMe / methanol / 1.25 h / 20 °C 3: 1.15 g / HCl / H₂O; ethanol / 16 h / 20 °C
	Multi-step reaction with 3 steps 1: 92 percent / hydrogen / 10 percent Pd/C / methanol / 16 h / 37503 Torr 2: 61 percent / MeLi / tetrahydrofuran / 16 h / 20 °C 3: 1.15 g / HCl / H₂O; ethanol / 16 h / 20 °C

Reference： [1]Birkholz, Mandy-Nicole; Dubrovina, Natalia V.; Jiao, Haijun; Michalik, Dirk; Holz, Jens; Paciello, Rocco; Breit, Bernhard; Boerner, Armin [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5896 - 5907]
[2]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]
[3]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]

15
[ 226393-36-8 ]
[ 226393-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: MeONa / methanol 1.2: 94 percent / aq. HCl 2.1: quinine
	Multi-step reaction with 2 steps 1: 95 percent / NaOMe / methanol / 1.25 h / 20 °C 2: 1.15 g / HCl / H₂O; ethanol / 16 h / 20 °C
	Multi-step reaction with 2 steps 1: 61 percent / MeLi / tetrahydrofuran / 16 h / 20 °C 2: 1.15 g / HCl / H₂O; ethanol / 16 h / 20 °C

Reference： [1]Birkholz, Mandy-Nicole; Dubrovina, Natalia V.; Jiao, Haijun; Michalik, Dirk; Holz, Jens; Paciello, Rocco; Breit, Bernhard; Boerner, Armin [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5896 - 5907]
[2]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]
[3]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]

16
[ 226393-33-5 ]
C₁₆H₁₇PBH₃CH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: 86 percent / KOH / methanol 3.1: 90 percent / DIPEA / tetrahydrofuran 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -65 °C 4.2: tetrahydrofuran; hexane

Reference： [1]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]

17
[ 226393-33-5 ]
((R,R)-2,5-diphenylphospholan-1-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: 86 percent / KOH / methanol

Reference： [1]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]

18
[ 226393-33-5 ]
C₁₆H₁₇PBH₃CH₂OCH₂SO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: 86 percent / KOH / methanol 3.1: 90 percent / DIPEA / tetrahydrofuran

Reference： [1]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]

19
[ 226393-33-5 ]
trifluoromethanesulfonic acid (R,R)-2,5-diphenyl-phospholan-1-ylmethyl ester borane adduct [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: 86 percent / KOH / methanol 3.1: 90 percent / Et₃N / CH₂Cl₂

Reference： [1]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]

20
[ 226393-33-5 ]
1,2-bis[(R,R)-2,5-diphenylphospholano]methane-borane adduct [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -65 °C 2.2: 61 percent / tetrahydrofuran; hexane / -65 - 20 °C
	Multi-step reaction with 4 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: 86 percent / KOH / methanol 3.1: 90 percent / DIPEA / tetrahydrofuran 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -65 °C 4.2: 12 percent / tetrahydrofuran; hexane
	Multi-step reaction with 4 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: 86 percent / KOH / methanol 3.1: 90 percent / Et₃N / CH₂Cl₂ 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -65 °C 4.2: 61 percent / tetrahydrofuran; hexane / -65 - 20 °C

Reference： [1]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]
[2]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]
[3]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]

21
[ 226393-33-5 ]
[ 933474-81-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: n-BuLi; TMEDA / tetrahydrofuran 3.1: DABCO
	Multi-step reaction with 3 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -65 °C 2.2: 61 percent / tetrahydrofuran; hexane / -65 - 20 °C 3.1: 99 percent / DABCO / toluene / 2 h / 60 °C
	Multi-step reaction with 5 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: 86 percent / KOH / methanol 3.1: 90 percent / DIPEA / tetrahydrofuran 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -65 °C 4.2: 12 percent / tetrahydrofuran; hexane 5.1: 99 percent / DABCO / toluene / 2 h / 60 °C

	Multi-step reaction with 5 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: 86 percent / KOH / methanol 3.1: 90 percent / DIPEA / tetrahydrofuran 4.1: n-BuLi; TMEDA / tetrahydrofuran 5.1: DABCO
	Multi-step reaction with 5 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: 86 percent / KOH / methanol 3.1: 90 percent / Et₃N / CH₂Cl₂ 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -65 °C 4.2: 61 percent / tetrahydrofuran; hexane / -65 - 20 °C 5.1: 99 percent / DABCO / toluene / 2 h / 60 °C

Reference： [1]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]
[2]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]
[3]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]
[4]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]
[5]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]

22
[ 226393-33-5 ]
(H₃C₁₆H₁₃P)2BH₃CH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: n-BuLi; TMEDA / tetrahydrofuran
	Multi-step reaction with 4 steps 1.1: PhSiH₃ / toluene 1.2: 83 percent / BH₃*Me₂S 2.1: 86 percent / KOH / methanol 3.1: 90 percent / DIPEA / tetrahydrofuran 4.1: n-BuLi; TMEDA / tetrahydrofuran

Reference： [1]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]
[2]Jackson, Mark; Lennon, Ian C. [Tetrahedron Letters, 2007, vol. 48, # 10, p. 1831 - 1834]

23
[ 226393-33-5 ]
[ 528565-79-9 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 1273 - 1275

24
[ 226393-33-5 ]
1,2-bis[(R,R)-2,5-diphenylphospholano]ethane oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: PhSiH₃ / toluene / 16 h / 110 °C 1.2: 95 percent / BH₃SMe₂ / tetrahydrofuran / 16 h / 20 °C 2.1: nBuLi / tetrahydrofuran; hexane / 1 h / -20 °C 2.2: 69 percent / tetrahydrofuran; hexane / 40 h / 20 °C 3.1: 92 percent / HBF₄OMe₂ / CH₂Cl₂ / 16 h / 20 °C 4.1: 98 percent / aq. H₂O₂ / CH₂Cl₂ / 16 h / 20 °C

Reference： [1]Pilkington, Christopher J.; Zanotti-Gerosa, Antonio [Organic Letters, 2003, vol. 5, # 8, p. 1273 - 1275]

25
[ 226393-33-5 ]
1,2-bis[(R,R)-2,5-diphenylphospholano]ethane-borane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: PhSiH₃ / toluene / 16 h / 110 °C 1.2: 95 percent / BH₃*SMe₂ / tetrahydrofuran / 16 h / 20 °C 2.1: nBuLi / tetrahydrofuran; hexane / 1 h / -20 °C 2.2: 69 percent / tetrahydrofuran; hexane / 40 h / 20 °C

Reference： [1]Pilkington, Christopher J.; Zanotti-Gerosa, Antonio [Organic Letters, 2003, vol. 5, # 8, p. 1273 - 1275]

26
[ 226393-33-5 ]
(R,R)-(+)-1-benzyl-1-r-oxo-2-c,5-t-diphenylphospholane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: oxalyl chloride / tetrahydrofuran / 2 h 2.1: lithium tri-tert-butoxyaluminohydride / diethyl ether / 20 °C 2.2: 70 percent / diethyl ether
	Multi-step reaction with 3 steps 1.1: oxalyl chloride / tetrahydrofuran / 2 h 2.1: LiAlH₄ / diethyl ether 2.2: 53 percent / H₂O / diethyl ether 3.1: n-BuLi / tetrahydrofuran / -78 °C 3.2: 50 percent / tetrahydrofuran

Reference： [1]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]
[2]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]

27
(1S,2S,5R)-1-Chloro-1-dimethylamino-2,5-diphenyl-2,5-dihydro-1H-phospholium; chloride [ No CAS ]
[ 226393-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 16.5 g / NaHCO₃; EDTA / CH₂Cl₂ / 4 h / 0 °C 2: 92 percent / hydrogen / 10 percent Pd/C / methanol / 16 h / 37503 Torr 3: 95 percent / NaOMe / methanol / 1.25 h / 20 °C 4: 1.15 g / HCl / H₂O; ethanol / 16 h / 20 °C
	Multi-step reaction with 4 steps 1: 16.5 g / NaHCO₃; EDTA / CH₂Cl₂ / 4 h / 0 °C 2: 92 percent / hydrogen / 10 percent Pd/C / methanol / 16 h / 37503 Torr 3: 61 percent / MeLi / tetrahydrofuran / 16 h / 20 °C 4: 1.15 g / HCl / H₂O; ethanol / 16 h / 20 °C

Reference： [1]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]
[2]Guillen, Frédéric; Rivard, Michael; Toffano, Martial; Legros, Jean-Yves; Daran, Jean-Claude; Fiaud, Jean-Claude [Tetrahedron, 2002, vol. 58, # 29, p. 5895 - 5904]

28
[ 538-81-8 ]
[ 226393-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) AlCl₃; 2.) NaHCO₃/EDTA / CH₂Cl₂ / -10 °C 2: hydrogen / Pd/C / CH₂Cl₂ / 16 h / 22800 - 38000 Torr 3: sodium methoxide / methanol / 16 h / Ambient temperature 4: 40 percent / aq. HCl / methanol

Reference： [1]Guillen, Frederic; Fiaud, Jean-Claude [Tetrahedron Letters, 1999, vol. 40, # 15, p. 2939 - 2942]

29
[ 949575-77-3 ]
[ 226393-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: hydrogen / Pd/C / CH₂Cl₂ / 16 h / 22800 - 38000 Torr 2: sodium methoxide / methanol / 16 h / Ambient temperature 3: 40 percent / aq. HCl / methanol

Reference： [1]Guillen, Frederic; Fiaud, Jean-Claude [Tetrahedron Letters, 1999, vol. 40, # 15, p. 2939 - 2942]

30
[ 226393-33-5 ]
(2R,5R)-2,5-Diphenyl-phospholane 1-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (COCl)2 / tetrahydrofuran 2: 63 percent / DIBAL-H

Reference： [1]Guillen, Frederic; Fiaud, Jean-Claude [Tetrahedron Letters, 1999, vol. 40, # 15, p. 2939 - 2942]

31
[ 226393-33-5 ]
(2R,5R)-1,2,5-Triphenyl-phospholane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: (COCl)2 / tetrahydrofuran 2: 63 percent / DIBAL-H 3: 88 percent / iPr₂NEt, dppp / <Pd(dba)2> 4: 1.) LiAlH₄, CeCl₃, BH₃*THF; 2.) DABCO / 2.) PhMe
	Multi-step reaction with 3 steps 1: (COCl)2 / tetrahydrofuran 2: 65 percent / tetrahydrofuran / -78 °C 3: 1.) LiAlH₄, CeCl₃, BH₃*THF; 2.) DABCO / 2.) PhMe

Reference： [1]Guillen, Frederic; Fiaud, Jean-Claude [Tetrahedron Letters, 1999, vol. 40, # 15, p. 2939 - 2942]
[2]Guillen, Frederic; Fiaud, Jean-Claude [Tetrahedron Letters, 1999, vol. 40, # 15, p. 2939 - 2942]

32
[ 226393-33-5 ]
(2R*,5R*)-(1,2,5)-triphenylphospholane-1-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: (COCl)2 / tetrahydrofuran 2: 63 percent / DIBAL-H 3: 88 percent / iPr₂NEt, dppp / <Pd(dba)2>
	Multi-step reaction with 2 steps 1: (COCl)2 / tetrahydrofuran 2: 65 percent / tetrahydrofuran / -78 °C

Reference： [1]Guillen, Frederic; Fiaud, Jean-Claude [Tetrahedron Letters, 1999, vol. 40, # 15, p. 2939 - 2942]
[2]Guillen, Frederic; Fiaud, Jean-Claude [Tetrahedron Letters, 1999, vol. 40, # 15, p. 2939 - 2942]

33
1-[(N,N)-dimethylamino]-1-r-oxo-2-t,5-t-diphenylphospholane [ No CAS ]
[ 226393-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methoxide / methanol / 16 h / Ambient temperature 2: 40 percent / aq. HCl / methanol

Reference： [1]Guillen, Frederic; Fiaud, Jean-Claude [Tetrahedron Letters, 1999, vol. 40, # 15, p. 2939 - 2942]

34
C₁₆H₁₇O₂P [ No CAS ]
[ 226393-33-5 ]
[ 474049-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	With Quinine In methanol Inert atmosphere; Reflux; Resolution of racemate;

Reference： [1]Location in patent: body text Goudriaan, P. Elsbeth; Jang, Xiao-Bin; Kuil, Mark; Lemmens, Renske; Van Leeuwen, Piet W. N. M.; Reek, Joost N. H. [European Journal of Organic Chemistry, 2008, # 36, p. 6079 - 6092]

35
[ 226393-33-5 ]
(2R,5R)-2,5-diphenylphospholane-borane complex [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.8 g	Stage #1: (R,R)-(+)-1-hydroxy-1-oxo-2,5-trans-diphenylphospholane With phenylsilane In toluene Inert atmosphere; Reflux; Stage #2: With dimethylsulfide borane complex In toluene at 20℃; for 16h; Inert atmosphere;

Reference： [1]Busacca, Carl A.; Farber, Elisa; Deyoung, Jay; Campbell, Scot; Gonnella, Nina C.; Grinberg, Nelu; Haddad, Nizar; Lee, Heewon; Ma, Shengli; Reeves, Diana; Shen, Sherry; Senanayake, Chris H. [Organic Letters, 2009, vol. 11, # 24, p. 5594 - 5597]

36
[ 1159633-63-2 ]
[ 226393-33-5 ]
[ 287733-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hydrogenchloride; water / methanol / 16 h / 60 °C 2: palladium on activated charcoal; hydrogen / ethanol / 3 h / 20 °C
	Multi-step reaction with 2 steps 1: hydrogenchloride; water / methanol / 20 h / 60 °C / Large scale 2: palladium on activated charcoal; hydrogen / ethanol / 3 h / 20 °C

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]
[2]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

37
[ 1159633-63-2 ]
[ 226393-33-5 ]
[ 474049-73-5 ]
[ 287733-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hydrogenchloride; water / methanol / 16 h / 60 °C 2: sodium; ammonia / tetrahydrofuran / 0.08 h / -78 °C
	Multi-step reaction with 2 steps 1: hydrogenchloride; water / methanol / 20 h / 60 °C / Large scale 2: sodium; ammonia / tetrahydrofuran / 0.08 h / -78 °C

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]
[2]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

38
[ 1159633-63-2 ]
[ 226393-33-5 ]
[ 474049-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: magnesium / methanol / 15 h / -20 °C 2: hydrogenchloride; water / methanol / 16 h / 60 °C
	Multi-step reaction with 2 steps 1: sodium tetrahydroborate; iodine / tetrahydrofuran / 6 h / 0 °C 2: hydrogenchloride; water / methanol / 16 h / 60 °C

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]
[2]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

39
[ 1159633-62-1 ]
[ 226393-33-5 ]
[ 287733-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / acetonitrile / 20 h / 50 °C 2: hydrogenchloride; water / methanol / 16 h / 60 °C 3: palladium on activated charcoal; hydrogen / ethanol / 3 h / 20 °C
	Multi-step reaction with 3 steps 1: 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / acetonitrile / 20 h / 50 °C 2: hydrogenchloride; water / methanol / 20 h / 60 °C / Large scale 3: palladium on activated charcoal; hydrogen / ethanol / 3 h / 20 °C

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]
[2]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

40
[ 1159633-62-1 ]
[ 226393-33-5 ]
[ 474049-73-5 ]
[ 287733-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / acetonitrile / 20 h / 50 °C 2: hydrogenchloride; water / methanol / 16 h / 60 °C 3: sodium; ammonia / tetrahydrofuran / 0.08 h / -78 °C
	Multi-step reaction with 3 steps 1: 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / acetonitrile / 20 h / 50 °C 2: hydrogenchloride; water / methanol / 20 h / 60 °C / Large scale 3: sodium; ammonia / tetrahydrofuran / 0.08 h / -78 °C

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]
[2]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

41
[ 1159633-62-1 ]
[ 226393-33-5 ]
[ 474049-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / acetonitrile / 20 h / 50 °C 2: magnesium / methanol / 15 h / -20 °C 3: hydrogenchloride; water / methanol / 16 h / 60 °C
	Multi-step reaction with 3 steps 1: 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / acetonitrile / 20 h / 50 °C 2: sodium tetrahydroborate; iodine / tetrahydrofuran / 6 h / 0 °C 3: hydrogenchloride; water / methanol / 16 h / 60 °C

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]
[2]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

42
[ 88123-43-7 ]
[ 226393-33-5 ]
[ 287733-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 16 h / 0 - 20 °C 1.2: 4 h / 0 °C 2.1: Cinchonin / acetonitrile / 20 h / 50 °C 3.1: hydrogenchloride; water / methanol / 16 h / 60 °C 4.1: palladium on activated charcoal; hydrogen / ethanol / 3 h / 20 °C
	Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 16 h / 0 - 20 °C 1.2: 4 h / 0 °C 2.1: Cinchonin / acetonitrile / 20 h / 50 °C 3.1: hydrogenchloride; water / methanol / 20 h / 60 °C / Large scale 4.1: palladium on activated charcoal; hydrogen / ethanol / 3 h / 20 °C

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]
[2]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

43
[ 88123-43-7 ]
[ 226393-33-5 ]
[ 474049-73-5 ]
[ 287733-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 16 h / 0 - 20 °C 1.2: 4 h / 0 °C 2.1: Cinchonin / acetonitrile / 20 h / 50 °C 3.1: hydrogenchloride; water / methanol / 16 h / 60 °C 4.1: sodium; ammonia / tetrahydrofuran / 0.08 h / -78 °C
	Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 16 h / 0 - 20 °C 1.2: 4 h / 0 °C 2.1: Cinchonin / acetonitrile / 20 h / 50 °C 3.1: hydrogenchloride; water / methanol / 20 h / 60 °C / Large scale 4.1: sodium; ammonia / tetrahydrofuran / 0.08 h / -78 °C

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]
[2]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

44
[ 88123-43-7 ]
[ 226393-33-5 ]
[ 474049-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 16 h / 0 - 20 °C 1.2: 4 h / 0 °C 2.1: Cinchonin / acetonitrile / 20 h / 50 °C 3.1: magnesium / methanol / 15 h / -20 °C 4.1: hydrogenchloride; water / methanol / 16 h / 60 °C
	Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 16 h / 0 - 20 °C 1.2: 4 h / 0 °C 2.1: Cinchonin / acetonitrile / 20 h / 50 °C 3.1: sodium tetrahydroborate; iodine / tetrahydrofuran / 6 h / 0 °C 4.1: hydrogenchloride; water / methanol / 16 h / 60 °C

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]
[2]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

45
(1S,2R,5S)-1-(diethylamino)-1-oxo-2,5-diphenyl-2,5-dideuterio-1H-phosphole [ No CAS ]
[ 226393-33-5 ]
[ 287733-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Cinchonin / acetonitrile / 20 h / 50 °C 2: hydrogenchloride; water / methanol / 16 h / 60 °C 3: palladium on activated charcoal; hydrogen / ethanol / 3 h / 20 °C
	Multi-step reaction with 3 steps 1: Cinchonin / acetonitrile / 20 h / 50 °C 2: hydrogenchloride; water / methanol / 20 h / 60 °C / Large scale 3: palladium on activated charcoal; hydrogen / ethanol / 3 h / 20 °C

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]
[2]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

46
(1S,2R,5S)-1-(diethylamino)-1-oxo-2,5-diphenyl-2,5-dideuterio-1H-phosphole [ No CAS ]
[ 226393-33-5 ]
[ 474049-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Cinchonin / acetonitrile / 20 h / 50 °C 2: magnesium / methanol / 15 h / -20 °C 3: hydrogenchloride; water / methanol / 16 h / 60 °C
	Multi-step reaction with 3 steps 1: Cinchonin / acetonitrile / 20 h / 50 °C 2: sodium tetrahydroborate; iodine / tetrahydrofuran / 6 h / 0 °C 3: hydrogenchloride; water / methanol / 16 h / 60 °C

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]
[2]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

47
[ 1159633-65-4 ]
[ 226393-33-5 ]
[ 287733-60-2 ]

Yield	Reaction Conditions	Operation in experiment
74.026 % de	With palladium on activated charcoal; hydrogen In ethanol at 20℃; for 3h;

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

48
[ 1159633-65-4 ]
[ 226393-33-5 ]
[ 474049-73-5 ]
[ 287733-60-2 ]

Yield	Reaction Conditions	Operation in experiment
82 % ee	With ammonia; sodium In tetrahydrofuran at -78℃; for 0.0833333h; Overall yield = 98 %; Overall yield = 0.0978 g;

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

49
[ 1428255-91-7 ]
[ 226393-33-5 ]
[ 474049-73-5 ]

Yield	Reaction Conditions	Operation in experiment
81 % ee	With hydrogenchloride; water In methanol at 60℃; for 16h; Overall yield = 75 %; Overall yield = 0.225 g;

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

50
[ 538-81-8 ]
[ 226393-33-5 ]
[ 287733-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 1.2: 4 h / 0 °C / Inert atmosphere 2.1: 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / acetonitrile / 20 h / 50 °C 3.1: hydrogenchloride; water / methanol / 16 h / 60 °C 4.1: palladium on activated charcoal; hydrogen / ethanol / 3 h / 20 °C
	Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 1.2: 4 h / 0 °C / Inert atmosphere 2.1: 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / acetonitrile / 20 h / 50 °C 3.1: hydrogenchloride; water / methanol / 20 h / 60 °C / Large scale 4.1: palladium on activated charcoal; hydrogen / ethanol / 3 h / 20 °C

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]
[2]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

51
[ 538-81-8 ]
[ 226393-33-5 ]
[ 474049-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 1.2: 4 h / 0 °C / Inert atmosphere 2.1: 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / acetonitrile / 20 h / 50 °C 3.1: magnesium / methanol / 15 h / -20 °C 4.1: hydrogenchloride; water / methanol / 16 h / 60 °C
	Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 1.2: 4 h / 0 °C / Inert atmosphere 2.1: 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / acetonitrile / 20 h / 50 °C 3.1: sodium tetrahydroborate; iodine / tetrahydrofuran / 6 h / 0 °C 4.1: hydrogenchloride; water / methanol / 16 h / 60 °C

Reference： [1]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]
[2]Hintermann, Lukas; Schmitz, Marco; Maltsev, Olegv.; Naumov, Pance [Synthesis, 2013, vol. 45, # 3, p. 308 - 325]

52
[ 226393-33-5 ]
[ 474049-73-5 ]

Yield	Reaction Conditions	Operation in experiment
23.6 g	With quinine In methanol Reflux;	1-2 Dissolve 2,5-diphenylphosphate racemate (5.4 g, 0.2 mol) in a minimum amount of refluxing methanol, then add quinine (6.5 g, 0.2 mol), cool to room temperature and collect the white precipitate and dissolve In dichloromethane, then decompose with aqueous NaOH solution (2N, 1000mL), wash the organic layer with NaOH solution (2N, 3×50mL) after decantation, then wash with brine, dry with MgSO4, and collect quinine under negative pressure; The aqueous phase was treated with concentrated HCl to obtain 23.6 g of the product, and the ee value of 2S,5S-diphenylphosphoric acid was 98.6%.

Reference： [1]Current Patent Assignee: ANHUI HYEA AROMAS CO LTD - CN116396331, 2023, A Location in patent: Paragraph 0025; 0029-0030; 0034

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CAS No. :	226393-33-5	MDL No. :	N/A
Formula :	C₁₆H₁₇O₂P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JXBQOEHGCNDFQE-HZPDHXFCSA-N
M.W :	272.28	Pubchem ID :	10978593
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-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.
P250	Do not subject to grinding/shock/friction.
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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 226393-33-5 ] {[proInfo.proName]}

Quality Control of [ 226393-33-5 ]

Related Doc. of [ 226393-33-5 ]

Product Details of [ 226393-33-5 ]

Safety of [ 226393-33-5 ]

Application In Synthesis of [ 226393-33-5 ]

[ 226393-33-5 ] Synthesis Path-Downstream 1~52

Similar Product of
[ 226393-33-5 ]

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 226393-33-5 ] {[proInfo.proName]}

Quality Control of [ 226393-33-5 ]

Related Doc. of [ 226393-33-5 ]

Product Details of [ 226393-33-5 ]

Safety of [ 226393-33-5 ]

Application In Synthesis of [ 226393-33-5 ]

[ 226393-33-5 ] Synthesis Path-Downstream 1~52

Similar Product of [ 226393-33-5 ]

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Similar Product of
[ 226393-33-5 ]