13807-91-5|1-(Benzyloxy)propan-2-ol| Ambeed

CAS No. :	13807-91-5
Formula :	C₁₀H₁₄O₂
M.W :	166.22
SMILES Code :	CC(O)COCC1=CC=CC=C1
MDL No. :	MFCD00085681
InChI Key :	KJBPYIUAQLPHJG-UHFFFAOYSA-N
Pubchem ID :	295955

Safety of [ 13807-91-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 13807-91-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.4
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	48.08
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	29.46 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.35
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.54
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.43
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.56
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.06
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.79

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.95
Solubility	1.88 mg/ml ; 0.0113 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.77
Solubility	2.84 mg/ml ; 0.0171 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.8
Solubility	0.263 mg/ml ; 0.00158 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.22 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.04

Application In Synthesis of [ 13807-91-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 13807-91-5 ]

[ 13807-91-5 ] Synthesis Path-Downstream 1~54

1
[ 2568-25-4 ]
[ 13807-91-5 ]
[ 33106-26-2 ]

References: [1]Gazzetta Chimica Italiana,1991,vol. 121,p. 445 - 447.
[2]Chemistry Letters,1983,p. 1593 - 1596.
[3]Gazzetta Chimica Italiana,1991,vol. 121,p. 445 - 447.

2
[ 2568-25-4 ]
[ 13807-91-5 ]
[ 33106-26-2 ]
[ 108-88-3 ]

References: [1]Bulletin des Societes Chimiques Belges,1991,vol. 100,p. 421 - 424.

3
[ 22539-93-1 ]
[ 13807-91-5 ]

References: [1]Synthesis,1987,p. 1007 - 1009.

4
[ 4254-15-3 ]
[ 100-39-0 ]
[ 13807-91-5 ]

References: [1]Agricultural and Biological Chemistry,1986,vol. 50,p. 2261 - 2272.
[2]Carbohydrate Research,1983,vol. 123,p. C25 - C28.
[3]Journal of the American Chemical Society,2012,vol. 134,p. 11124 - 11127.

5
[ 13807-91-5 ]
[ 89387-41-7 ]
[ 89387-46-2 ]
[ 89387-45-1 ]

References: [1]Carbohydrate Research,1983,vol. 123,p. C25 - C28.

6
[ 13807-91-5 ]
[ 89387-41-7 ]
1-O-benzyl-2-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-3-deoxy-2(S)-glycerol [ No CAS ]
[ 108811-18-3 ]

References: [1]Agricultural and Biological Chemistry,1986,vol. 50,p. 2261 - 2272.

7
[ 13807-91-5 ]
2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxaphospholidin-2-<17O>one [ No CAS ]
C₂₀H₂₆NO₃⁽¹⁷⁾OP [ No CAS ]

References: [1]Journal of the American Chemical Society,1984,vol. 106,p. 4916 - 4922.

8
[ 13807-91-5 ]
[ 89401-28-5 ]

References: [1]Carbohydrate Research,1983,vol. 123,p. C25 - C28.

9
[ 13807-91-5 ]
[ 4254-15-3 ]

References: [1]Synthesis,1987,p. 1007 - 1009.

10
[(S)-2-(1-Ethoxy-ethoxy)-propoxymethyl]-benzene [ No CAS ]
[ 13807-91-5 ]

References: [1]Synthesis,1991,p. 832 - 834.

11
[ 13807-91-5 ]
[ 598-21-0 ]
[ 125749-46-4 ]

References: [1]Synthetic Communications,1989,vol. 19,p. 2035 - 2040.

12
[ 13807-91-5 ]
[ 98-59-9 ]
[ 119233-39-5 ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; toluene;	A mixture of this (S)-1-benzyloxy-2-hydroxypropane (60 g, 0.36 mol) with anhydrous pyridine (300 g) was cooled with ice, followed by dropwise adding a solution of p-toluenesulfonyl chloride (75.8 g, 0.20 mol) in pyridine (70 ml) at 0 C., agitating the mixture at room temperature for 3 hours, adding toluene (800 ml), agitating the mixture, several times washing the resulting organic layer with water, drying it over anhydrous magnesium sulfate and distilling off toluene to obtain (S)-1-benzyloxy-2-(p-toluenesulfonyloxy)propane (115.2 g).

References: [1]Synthesis,1991,p. 832 - 834.
[2]Tetrahedron,1999,vol. 55,p. 1491 - 1504.
[3]Patent: US5080827,1992,A .

13
[ 85483-96-1 ]
[ 13807-91-5 ]

References: [1]Chemistry - An Asian Journal,2011,vol. 6,p. 149 - 156.
[2]Journal of the American Chemical Society,2000,vol. 122,p. 6175 - 6182.
[3]Journal of Organic Chemistry,2009,vol. 74,p. 8154 - 8163.
[4]Journal of the American Chemical Society,1984,vol. 106,p. 4916 - 4922.
[5]Tetrahedron Asymmetry,1995,vol. 6,p. 1873 - 1876.
[6]Journal of the Chemical Society. Perkin transactions I,1997,p. 3227 - 3236.
[7]Tetrahedron Asymmetry,2006,vol. 17,p. 2538 - 2547.

14
[ 13807-91-5 ]
[ 4753-07-5 ]
Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-((S)-2-benzyloxy-1-methyl-ethoxy)-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester [ No CAS ]

References: [1]Agricultural and Biological Chemistry,1986,vol. 50,p. 2261 - 2272.

15
[ 22539-93-1 ]
[ 13807-91-5 ]
[ 89401-28-5 ]

References: [1]Acta Chemica Scandinavica,1994,vol. 48,p. 506 - 510.

16
[ 50-00-0 ]
[ 13807-91-5 ]
((S)-2-Chloromethoxy-propoxymethyl)-benzene [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1390 - 1409.

17
[ 100-39-0 ]
[ 76946-21-9 ]
[ 13807-91-5 ]

References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1390 - 1409.

18
[ 13807-91-5 ]
[ 535-11-5 ]
2-((S)-2-Benzyloxy-1-methyl-ethoxy)-propionic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron Asymmetry,1995,vol. 6,p. 1873 - 1876.
[2]Journal of the Chemical Society. Perkin transactions I,1997,p. 3227 - 3236.

19
[ 13807-91-5 ]
[ 13807-91-5 ]

References: [1]Tetrahedron Asymmetry,1996,vol. 7,p. 3187 - 3192.

20
(R)-1-Benzyloxy-3-phenylsulfanyl-propan-2-ol [ No CAS ]
[ 13807-91-5 ]

References: [1]Tetrahedron,1997,vol. 53,p. 12883 - 12894.

21
(R)-1-Benzyloxy-3-benzylsulfanyl-propan-2-ol [ No CAS ]
[ 13807-91-5 ]

References: [1]Tetrahedron,1997,vol. 53,p. 12883 - 12894.

22
[ 13807-91-5 ]
[ 98-74-8 ]
[ 221310-60-7 ]

References: [1]Tetrahedron,1999,vol. 55,p. 1491 - 1504.

23
[ 2568-25-4 ]
[ 4799-68-2 ]
[ 13807-91-5 ]
[ 33106-26-2 ]

References: [1]Organic Preparations and Procedures International,1991,vol. 23,p. 427 - 431.

24
[ 62921-76-0 ]
[ 13807-91-5 ]
[ 287171-13-5 ]

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 6175 - 6182.

25
[ 13807-91-5 ]
[ 7460-82-4 ]
[ 857682-82-7 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 4609 - 4616.
[2]Tetrahedron Asymmetry,2006,vol. 17,p. 2538 - 2547.

26
[ 62921-74-8 ]
[ 13807-91-5 ]
[ 885620-02-0 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 5923 - 5929.

27
[ 13807-91-5 ]
[ 19249-03-7 ]
C₂₆H₃₈O₆ [ No CAS ]

References: [1]Tetrahedron Asymmetry,2006,vol. 17,p. 2538 - 2547.

28
[ 124-63-0 ]
[ 13807-91-5 ]
[ 948996-19-8 ]

Yield	Reaction Conditions	Operation in experiment
53 g	With N-ethyl-N,N-diisopropylamine; In toluene; at 0 - 20℃; for 1h;	The starting compound (S) - 1 - (benzyloxy) propan-2-ol (36g, 217mmol) and diisopropyl ethylamine (39.2g, 303mmol) dissolved in toluene (540 ml) in. In 0 C add a sulfonyl chloride (2.32 ml, 29 . 8mmol), then stirring 2 hours, then the stirring at room temperature 1 hour. After the completion of reaction, water (500 ml) to and toluene (200 ml, two) extraction. First organic layer and ammonium chloride aqueous solution (200 ml) and saturated aqueous sodium chloride solution (200 ml) washing and extraction. Organic layer is dried with anhydrous sodium sulfate, filtered and concentrated. Residue after drying. Generating title compound (53g).
53 g	With N-ethyl-N,N-diisopropylamine; In toluene; at 0 - 20℃; for 3h;	Starting compound (S)-1-(benzyloxy)propan-2-ol (36 g, 217 mmol) and diisopropylethylamine (39.2 g, 303 mmol) were dissolved in toluene (540 mL). methane sulfonyl chloride (2.32 ml, 29.8 mmol) was added at 0 C., followed by stirring for 2 hr and stirring more at room temperature for 1 hr. After reaction was finished, extraction was performed with water (500 ml) and toluene (200 ml, twice). The organic layer was extracted by saturated ammonium chloride aqueous solution (200 ml) and saturated sodium chloride aqueous solution (200 ml), and washed. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was dried. The title compound (53 g) was produced. 1H-NMR (CDCl3, Varian 400 MHz): delta 1.40 (3H, d, J=6.4 Hz), 3.01 (3H, s), 3.52-3.61 (2H, m), 4.55 & 4.57 (2H, ABq, JAB=11.8 Hz), 4.88-4.96 (1H, m), 7.26-7.38 (5H, m).

References: [1]Tetrahedron Letters,2007,vol. 48,p. 5665 - 5668.
[2]Patent: CN105452259,2016,A .Location in patent: Paragraph 0163; 0164; 0165; 0166.
[3]Patent: US2016/168167,2016,A1 .Location in patent: Paragraph 0127-0129.

29
[ 13807-91-5 ]
(R,R)-bis(2-benzyloxy-1-methylethyl)phosphine borane complex [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 5665 - 5668.

30
[ 13807-91-5 ]
(R,R,R)-tris(2-benzyloxy-1-methylethyl)phosphane borane complex [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 5665 - 5668.
[2]Tetrahedron Letters,2007,vol. 48,p. 5665 - 5668.

31
[ 100-44-7 ]
sodium-compound of acetoacetanilide [ No CAS ]
[ 13807-91-5 ]

References: [1]Tetrahedron Asymmetry,2006,vol. 17,p. 2538 - 2547.

32
[ 13807-91-5 ]
[ 221310-61-8 ]

References: [1]Tetrahedron,1999,vol. 55,p. 1491 - 1504.

33
[ 13807-91-5 ]
[ 199991-74-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 3227 - 3236.
[2]Tetrahedron Asymmetry,1995,vol. 6,p. 1873 - 1876.

34
[ 2930-05-4 ]
[ 13807-91-5 ]

References: [1]Chemical Communications,2018,vol. 54,p. 7243 - 7246.
[2]Tetrahedron,1997,vol. 53,p. 12883 - 12894.
[3]Tetrahedron,1997,vol. 53,p. 12883 - 12894.

35
[ 13807-91-5 ]
[ 138247-62-8 ]

References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 1390 - 1409.

36
[ 13807-91-5 ]
[ 89387-47-3 ]

References: [1]Agricultural and Biological Chemistry,1986,vol. 50,p. 2261 - 2272.

37
[ 13807-91-5 ]
C₆₃H₇₆O₂₄ [ No CAS ]

References: [1]Agricultural and Biological Chemistry,1986,vol. 50,p. 2261 - 2272.

38
[ 13807-91-5 ]
1-O-benzyl-2-O-<4-O-(α-D-glucopyranosyl)-β-D-glucopyranosyl>-3-deoxy-2(S)-glycerol [ No CAS ]

References: [1]Agricultural and Biological Chemistry,1986,vol. 50,p. 2261 - 2272.

39
[ 13807-91-5 ]
[ 128693-47-0 ]

References: [1]Synthesis,1991,p. 832 - 834.

40
[ 13807-91-5 ]
[ 64190-49-4 ]

References: [1]Synthesis,1991,p. 832 - 834.

41
[ 13807-91-5 ]
2-((S)-2-Benzyloxy-1-methyl-ethyl)-malonic acid [ No CAS ]

References: [1]Synthesis,1991,p. 832 - 834.

42
[ 13807-91-5 ]
2-((R)-2-Benzyloxy-1-methyl-ethyl)-malonic acid [ No CAS ]

References: [1]Synthesis,1991,p. 832 - 834.

43
[ 13807-91-5 ]
[ 138485-77-5 ]

References: [1]Synthesis,1991,p. 832 - 834.

44
[ 13807-91-5 ]
[ 138485-77-5 ]

References: [1]Synthesis,1991,p. 832 - 834.

45
[ 4039-82-1 ]
[ 13807-91-5 ]

References: [1]Synthesis,1987,p. 1007 - 1009.

46
[ 100-44-7 ]
disodium-compound of 1,1,2,2-tetraphenyl-ethane [ No CAS ]
[ 13807-91-5 ]

References: [1]Synthesis,1987,p. 1007 - 1009.

47
[ 13807-91-5 ]
[ 89387-47-3 ]

References: [1]Carbohydrate Research,1983,vol. 123,p. C25 - C28.

48
[ 13807-91-5 ]
[ 89387-44-0 ]

References: [1]Carbohydrate Research,1983,vol. 123,p. C25 - C28.

49
[ 13807-91-5 ]
[ 89387-43-9 ]

References: [1]Carbohydrate Research,1983,vol. 123,p. C25 - C28.

50
[ 4254-15-3 ]
[ 100-44-7 ]
[ 18162-48-6 ]
[ 13807-91-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; potassium hydroxide; triethylamine; In dichloromethane;	(c) (S)-(-)-1-Benzyloxy-2propanol A mixture of powdered KOH (5.90 g, 105 mmol), (S)-(+)-1,2-propanediol (8.00 g, 105 mmol) and benzyl chloride (13.3 g, 105 mmol) was heated at 130 C. for 2 hours. The mixture was cooled to room temperature, diluted with water and extracted with Et2 O layer was separated and washed with brine, dried over MgSO4, filtered and concentrated to provide 14.49 g of crude product which was dissolved in dichloromethane (50 mL). Triethyl amine (4.90 g, 48.4 mmol), DMAP (0.48 g, 3.93 mmol) and tert-butyldimethylsilyl chloride (6.5 g, 43.2 mmol) were added and the resulting solution was stirred at room temperature ca. 18 hours. The solution was then washed with H2 O and brine, dried over MgSO4, filtered and concentrated in vacuo providing a crude oil. Flash chromatography on silica gel eluding with 27.5% EtOAc/hexanes provided (s)-(-)-1-Benzyloxy-2-propanol (4.12 g, 24.8 mmol, 24%) as a nearly colorless oil: [alpha]D20 =+5.36 (c=3.30, MeOH); 1 H NMR (CDCl3) delta 7.4-7.3 (5H, m), 4.56 (2H, s), 4.01 (1H, ddq, J=8.2, 6.3, 3), 3.48 (1H, dd, J=9.3, 3), 3.28 (1H, dd, J=9.3, 8.2), 2.05 (1H, br), 1.15 (3H, d, J=6.3); CIMS m/z 189 (M+23, 100); Anal. Calcd for C10 H14 O2.circle-solid.(0.1 H2 O): C, 71.49; H, 8.52; Found: C, 71.34; H, 8.51.

References: [1]Patent: US6110961,2000,A .

51
[ 1663-39-4 ]
[ 13807-91-5 ]
[ 1073630-36-0 ]

Yield	Reaction Conditions	Operation in experiment
51.9%	With sodium hydride; at 0℃; for 0.166667h;	Cool a mixture of 20 g (120.3 mmol) (+)-(S)-1-benzyloxy-2-propanol and 123 g (962 mmol) tert.-butyl acrylate to 0 C. and add 962 mg (24 mmol, 60%) sodium hydride in several portions. Stir the mixture for 10 min at 0 C., then carefully add satd. ammonium chloride solution. After phase separation, extract the aqueous phase twice with dichloromethane. Combine the organic phases, dry over magnesium sulphate and concentrate under vacuum, then at high vacuum. Purify the raw product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 30:1). 18.4 g of the target compound (51.9% of theor.) is obtained. 1H-NMR (400 MHz, DMSO-d6): delta=7.38-7.25 (m, 5H), 4.49 (s, 2H), 3.64 (t, 2H), 3.61-3.58 (m, 1H), 3.40 (dd, 1H), 3.32 (dd, 1H), 2.39 (t, 2H), 1.39 (s, 9H), 1.05 (d, 3H).
51.9%	With sodium hydride; at 0℃; for 0.166667h;	Example 39A tert-Butyl 3-[(1S)-2-benzyloxy-1-methylethoxy]propanoate A mixture of 20 g (120.3 mmol) of (+)-(S)-1-benzyloxy-2-propanol and 123 g (962 mmol) of tert-butyl acrylate is cooled to 0 C., and 962 mg (60% strength, 24 mmol) of sodium hydride are added in a plurality of portions. The mixture is stirred at 0 C. for 10 min, and saturated aqueous ammonium chloride solution is then added carefully. After phase separation, the aqueous phase is extracted twice with dichloromethane. The organic phases are combined, dried over magnesium sulfate and concentrated under reduced pressure and then under high vacuum. The crude product is purified by chromatography on silica gel (cyclohexane/ethyl acetate 30:1). This gives 18.4 g of the target compound (51.9% of theory). 1H-NMR (400 MHz, DMSO-d6): delta=7.38-7.25 (m, 5H), 4.49 (s, 2H), 3.64 (t, 2H), 3.61-3.58 (m, 1H), 3.40 (dd, 1H), 3.32 (dd, 1H), 2.39 (t, 2H), 1.39 (s, 9H), 1.05 (d, 3H).

References: [1]Patent: US2009/318475,2009,A1 .Location in patent: Page/Page column 29.
[2]Patent: US2011/166163,2011,A1 .Location in patent: Page/Page column 31.

52
[ 50586-80-6 ]
[ 13807-91-5 ]
[ 1194230-68-6 ]

References: [1]Chemistry - An Asian Journal,2011,vol. 6,p. 149 - 156.
[2]Journal of Organic Chemistry,2009,vol. 74,p. 8154 - 8163.

53
[ 13807-91-5 ]
[ 13807-91-5 ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 2039 - 2043.
[2]Organometallics,2011,vol. 30,p. 6347 - 6350.

54
[ 945001-27-4 ]
[ 13807-91-5 ]
C₂₃H₂₀Cl₂N₄O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%		NaH (480 mg, 12 mmol, 60% dispersion in oil) was added at room temperature to a flask containing (S)-(+)-l-Benzyloxy-2-propanol (2.Og, 12 mmol) in THF (15 mL). After stirring for 30 minutes, 5-amino-4-(3,4-dichlorophenyl)-2-(methylsulfinyl) thiopheno[2,3- d]pyrimidine-6-carboxamide (400 mg, 1 mmol) was added and the mixture was stirred at room temperature for 15 minutes The reaction was quenched with water (1OmL) and the solvent was evaporated. The crude product was passed through a plug of silica gel (eluting with 1 :1 hexane/EtOAc), dried over Na2SO4, and evaporated to dryness. The crude material (300 mg, 0.6 mmol) was dissolved in DCM (2OmL) and cooled to -45 0C. BBr3 (1.2 mmol) was added and the mixture was stirred for 5 minutes then quenched with MeOH (5 mL). The solvent was removed in vacuo and the residue was dissolved in EtOAc. The organic layer <n="206"/>was washed with aqueous NaHCO3 and dried over Na2SO4. The product was purified using reverse-phase preparative HPLC (20-60% acetonitrile, 0.1% TFA, 30 minutes). The appropriate fractions were combined and concentrated on a rotary evaporator. The residue was dissolved in ethyl acetate (100 mL), washed with aqueous NaHCO3, and dried over Na2SO4. The solvent was removed in vacuo to give 10 mg (2.4%) of product as a light yellow solid. 1H NMR (400 MHz, D6-DMSO) delta ppm 7.93 (d, IH, J= 1.6 Hz), 7.82 (d, IH, J = 8 Hz), 7.65 (dd, IH, J= 2, 8.4 Hz), 7.27 (s, 2H), 6.32 (bs, 2H), 5.23 (m, IH), 4.93 (t, IH, J = 5.6 Hz), 3.59 (m, 2H), 1.29 (d, 3H, J= 6 Hz). MS m/z calculated for (M + H)+ 413, found 413.

References: [1]Patent: WO2007/84560,2007,A2 .Location in patent: Page/Page column 204-205.

Historical Records

Technical Information

• Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Nomenclature of Ethers • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Preparation of Ethers • Reactions of Alcohols • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Swern Oxidation

Related Functional Groups of
[ 13807-91-5 ]

Aryls

A100618 [85483-97-2]

(S)-1-Benzyloxy-2-propanol

Similarity: 1.00

A140836 [89401-28-5]

(R)-1-(Benzyloxy)propan-2-ol

Similarity: 1.00

A120722 [14618-80-5]

(R)-2-((Benzyloxy)methyl)oxirane

Similarity: 0.97

A166342 [16495-13-9]

(S)-2-((Benzyloxy)methyl)oxirane

Similarity: 0.97

A183466 [4799-67-1]

3-(Benzyloxy)propane-1,2-diol

Similarity: 0.97

Ethers

A100618 [85483-97-2]

(S)-1-Benzyloxy-2-propanol

Similarity: 1.00

A140836 [89401-28-5]

(R)-1-(Benzyloxy)propan-2-ol

Similarity: 1.00

A120722 [14618-80-5]

(R)-2-((Benzyloxy)methyl)oxirane

Similarity: 0.97

A166342 [16495-13-9]

(S)-2-((Benzyloxy)methyl)oxirane

Similarity: 0.97

A183466 [4799-67-1]

3-(Benzyloxy)propane-1,2-diol

Similarity: 0.97

Alcohols

A100618 [85483-97-2]

(S)-1-Benzyloxy-2-propanol

Similarity: 1.00

A140836 [89401-28-5]

(R)-1-(Benzyloxy)propan-2-ol

Similarity: 1.00

A183466 [4799-67-1]

3-(Benzyloxy)propane-1,2-diol

Similarity: 0.97

A276557 [70448-03-2]

2-(Benzyloxy)propan-1-ol

Similarity: 0.97

A173556 [868594-48-3]

1-Phenyl-2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-ol

Similarity: 0.93

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CAS No.: 13807-91-5

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CAS No.: 13807-91-5

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CAS No.: 13807-91-5

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Physicochemical Properties

Lipophilicity

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[ 13807-91-5 ] Synthesis Path-Downstream 1~54

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Aryls

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