[ CAS No. 86087-24-3 ]

Name: 86087-24-3|(R)-Tetrahydrofuran-3-ol|98%
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Quality Control of [ 86087-24-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 86087-24-3 ]

CAS No. :	86087-24-3	MDL No. :	MFCD00067101
Formula :	C₄H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XDPCNPCKDGQBAN-SCSAIBSYSA-N
M.W :	88.11	Pubchem ID :	641512
Synonyms :

Calculated chemistry of [ 86087-24-3 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	21.47
TPSA :	29.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.35
Log Po/w (XLOGP3) :	-0.41
Log Po/w (WLOGP) :	-0.23
Log Po/w (MLOGP) :	-0.57
Log Po/w (SILICOS-IT) :	0.84
Consensus Log Po/w :	0.19

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.13
Solubility :	65.6 mg/ml ; 0.745 mol/l
Class :	Very soluble
Log S (Ali) :	0.26
Solubility :	159.0 mg/ml ; 1.8 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	0.18
Solubility :	133.0 mg/ml ; 1.51 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.93

Safety of [ 86087-24-3 ]

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

Application In Synthesis of [ 86087-24-3 ]

* 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.

Upstream synthesis route of [ 86087-24-3 ]
Downstream synthetic route of [ 86087-24-3 ]

[ 86087-24-3 ] Synthesis Path-Upstream 1~23

1
[ 125605-10-9 ]
[ 86087-24-3 ]

Yield	Reaction Conditions	Operation in experiment
99.1%	With hydrogenchloride; sodium hydroxide In methanol; water	EXAMPLE 5 Preparation of (R)-3-Hydroxytetrahydrofuran To 35 g (0.28 mol) of the (R)-4-chloro-1,3-butanediol obtained in Reference Example 2 hereinafter given was added 70 ml of 0.5N hydrochloric acid, followed by heating under reflux for 2 hours. After cooling, the reaction mixture was neutralized with a 50percent aqueous solution of sodium hydroxide, and water was evaporated under reduced pressure. To the residual mixture of crystals and an oily substance was added 60 ml of methanol, followed by stirring. The crystals were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was distilled under reduced pressure to give 16.6 g of the title compound as a colorless substance (purity: 99.1percent; yield: 67percent). Optical rotation: [α]_D²³ =-15.91° (c=2.45, methanol)
88%	for 16 h; Heating / reflux	Example 4; [66] 800 mL of toluene was added to 218 g (1.758 mol) of (No.)-4-chloro-l,3-butanediol prepared in Example 3, and stirring was performed for 16 hours under reflux. The reaction mixture was cooled to room temperature and, after adding 37.3 g (0.352 mol) of Na₂CO₃ and 1 g (0.055 mol) of water, stirring was further performed for 30 minutes. After removing solid by filtering, the solvent was recovered by concentration under reduced pressure, and the residue was further distilled under reduced pressure. 137 g of colorless (/?)-3-hydroxytetrahydrofuran was obtained (yield = 88percent, overall yield = 85percent, optical purity = 99.52percent ee).
73.62 g	for 2 h; Reflux	Dilute hydrochloric acid (17.5 ml of conc. hydrochloric acid diluted with 332.50 ml of water) was added to (R)-4-chloro-1,3-butanediol (175 g) and stirring was performed for 2 hours under reflux. After completion of the reaction monitored by gas chromatography, the reaction mixture was cooled to 0 to 5°C followed by a pH adjustment between 7 to 8 by using aqueous sodium hydroxide solution (82.5 g of sodium hydroxide dissolved in 165 ml of water). The resulting reaction mass was diluted with methanol (525 ml) followed by distillation under reduced pressure maintaining temperature below 45°C. Water was completely removed using methanol stripping (2 x 525 ml) followed by addition of methyl tert-butyl ether (525 ml) to the concentrated mass. The resulting suspension was stirred for 30 minutes followed by filtration to remove inorganic materials. The solid cake was washed with methyl tert-butyl ether (100 ml) followed by distillation under reduced pressure maintaining temperature below 40°C to obtain a crude oil (88.46 g). The resulting crude material was distilled under reduced pressure at 90 to 95°C (5 mmHg pressure) to give pure (R)-tetrahydrofuran-3-ol as an oil (73.62 g, 59.47 percent).1H-NMR: (400 MHz, CDC13): ö: 4.44-4.45 (m, 1H), 3.90-3.97 (m, 1H), 3.69-3.80 (m, 2H), 3.02-3. 12 (brs, 1H), 2.00-2.08 (m, 1H), 1.84-2.00 (m, 1H)Mass [M+Hj: 88.81 Purity by GC: 99.43percent areaSpecific optical Rotation (C= 1, Methanol): -17.57°

Reference： [1] Patent: US5780649, 1998, A,
[2] Patent: WO2008/93955, 2008, A1, . Location in patent: Paragraph 65-66
[3] Patent: WO2016/21192, 2016, A1, . Location in patent: Paragraph 0085

2
[ 70005-88-8 ]
[ 86087-24-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	at 100℃;	Example 4; 5 g of the catalyst used in Example 1 was loaded into a completely automated continuous fixed-bed reactor made of 316 stainless steel, after which the internal temperature of the reactor was adjusted to 100°C and then a dioxane solution containing 10 wtpercent of (R)- 1,2,4- butanetriol (optical purity of 99.0percent) was fed into the reactor at a WHSV of 2.0 h^~ to thus <n="8"/>conduct the reaction.The results of the preparation of (R)-3-tetrahydrofuran are shown in Table 3 below.

Reference： [1] Patent: WO2007/81065, 2007, A1, . Location in patent: Page/Page column 6-7
[2] Journal of Organic Chemistry, 1983, vol. 48, # 16, p. 2767 - 2769

3
[ 42890-76-6 ]
[ 106-97-8 ]
[ 86087-24-3 ]

Yield	Reaction Conditions	Operation in experiment
54%	With CH₃SO₃H In water	EXAMPLE 4 Preparation of (R)-3-hydroxytetrahydrofuran To a mixture of (S)-1,2,4-trimesyloxy butane (10 g), prepared as in HETEROCYCLES vol.24 N° 5, 1986 p.1331, starting from (S)-1,2,4-butanetriol having e.e. >99percent, in H₂O (200 ml) CH₃SO₃H (5.6g) is added. The temperature is left to rise up to 80° C. and kept for 27h. After cooling to r.t. the mixture is treated in batch with IRA 410 (OH-form) (0.2 L). The resin is filtered off, and washed with H₂O; the filtrate gives, after distillation and chromatographic purification (R)-3-hydroxytetrahydrofuran with 94percent e.e. (yield 54percent).

Reference： [1] Patent: US2003/32818, 2003, A1,

4
[ 1358604-08-6 ]
[ 86087-24-3 ]

Reference： [1] Patent: WO2017/130217, 2017, A1, . Location in patent: Page/Page column 22; 35

5
[ 27999-96-8 ]
[ 86087-24-3 ]

Reference： [1] Patent: CN106957287, 2017, A, . Location in patent: Paragraph 0042

6
[ 778-29-0 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1] Tetrahedron Asymmetry, 2012, vol. 23, # 11-12, p. 898 - 903

7
[ 453-20-3 ]
[ 108-05-4 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1] Tetrahedron Asymmetry, 2012, vol. 23, # 8, p. 583 - 586

8
[ 22929-52-8 ]
[ 86087-24-3 ]

Reference： [1] ACS Catalysis, 2016, vol. 6, # 3, p. 1598 - 1605
[2] ChemBioChem, 2018, vol. 19, # 3, p. 239 - 246

9
[ 22929-52-8 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1] ChemBioChem, 2018, vol. 19, # 3, p. 239 - 246
[2] ChemBioChem, 2018, vol. 19, # 3, p. 239 - 246

10
[ 453-20-3 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1] Tetrahedron Asymmetry, 2000, vol. 11, # 23, p. 4781 - 4790

11
[ 27999-96-8 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1] Angewandte Chemie - International Edition, 2001, vol. 40, # 22, p. 4201 - 4204

12
[ 27999-96-8 ]
[ 86087-24-3 ]

Reference： [1] FEBS Journal, 2013, vol. 280, # 13, p. 3084 - 3093

13
[ 1191-99-7 ]
[ 86087-24-3 ]

Reference： [1] Heterocycles, 1989, vol. 28, # 1, p. 283 - 294
[2] Journal of the American Chemical Society, 1986, vol. 108, # 8, p. 2049 - 2054

14
[ 1708-29-8 ]
[ 86087-24-3 ]

Reference： [1] Journal of the American Chemical Society, 1986, vol. 108, # 8, p. 2049 - 2054

15
[ 145873-44-5 ]
[ 1708-29-8 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1] Liebigs Annales, 1997, # 9, p. 1877 - 1879
[2] Liebigs Annales, 1997, # 9, p. 1877 - 1879

16
[ 778-29-0 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1] Tetrahedron Asymmetry, 2012, vol. 23, # 11-12, p. 898 - 903

17
[ 453-20-3 ]
[ 108-05-4 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1] Tetrahedron Asymmetry, 2012, vol. 23, # 8, p. 583 - 586

18
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1] Synthesis (Germany), 2013, vol. 45, # 7, p. 931 - 935

19
[ 22929-52-8 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1] ChemBioChem, 2018, vol. 19, # 3, p. 239 - 246
[2] ChemBioChem, 2018, vol. 19, # 3, p. 239 - 246

20
[ 453-20-3 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1] Tetrahedron Asymmetry, 2000, vol. 11, # 23, p. 4781 - 4790

21
[ 27999-96-8 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1] Angewandte Chemie - International Edition, 2001, vol. 40, # 22, p. 4201 - 4204

22
[ 145873-44-5 ]
[ 1708-29-8 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1] Liebigs Annales, 1997, # 9, p. 1877 - 1879
[2] Liebigs Annales, 1997, # 9, p. 1877 - 1879

23
[ 864070-18-8 ]
[ 86087-24-3 ]
[ 915095-89-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 10, p. 4173 - 4184

[ 86087-24-3 ] Synthesis Path-Downstream 1~68

1
[ 1191-99-7 ]
[ 86087-24-3 ]

Reference： [1]Heterocycles,1989,vol. 28,p. 283 - 294
[2]Journal of the American Chemical Society,1986,vol. 108,p. 2049 - 2054

2
[ 1708-29-8 ]
[ 86087-24-3 ]

Reference： [1]Journal of the American Chemical Society,1986,vol. 108,p. 2049 - 2054

3
[ 70005-88-8 ]
[ 86087-24-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	strong acid ion exchange resin (Amberlyst 15, H+ form); In 1,4-dioxane; at 100℃; under 760.051 Torr;Product distribution / selectivity;	Example 4; 5 g of the catalyst used in Example 1 was loaded into a completely automated continuous fixed-bed reactor made of 316 stainless steel, after which the internal temperature of the reactor was adjusted to 100C and then a dioxane solution containing 10 wt% of (R)- 1,2,4- butanetriol (optical purity of 99.0%) was fed into the reactor at a WHSV of 2.0 h~ to thus <n="8"/>conduct the reaction.The results of the preparation of (R)-3-tetrahydrofuran are shown in Table 3 below.

Reference： [1]Patent: WO2007/81065,2007,A1 .Location in patent: Page/Page column 6-7
[2]Journal of Organic Chemistry,1983,vol. 48,p. 2767 - 2769

4
[ 86087-24-3 ]
[ 124-63-0 ]
[ 150406-31-8 ]

Yield	Reaction Conditions	Operation in experiment
100%		At room temperature,(R) -tetrahydrofuran-3-ol 19a (7.05 g, 80.0 mmol) was dissolved in dichloromethane (80 mL)After cooling to 0 C, triethylamine (10.5 g, 104.0 mmol) was added and stirred for 10 minutes. Methylsulfonyl chloride (10.94 g, 96.0 mmol) was added dropwise to the reaction mixture, and the reaction was stirred at room temperature for 4 hours.The reaction solution was filtered and the filter cake was washed with dichloromethane (30 mL x 3). The combined organic phases were washed successively with water (30 mL x 2) and saturated brine solution (30 mL x 2).Dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give a pale yellow liquid 19b (10.2 g, yield 100%).
99%	With triethylamine; In dichloromethane; at 0 - 20℃; for 12h;	To a solution of(R)-tetrahydrofuran-3-ol (25 g, 253.7 mmol) in DCM (250 mL) at 0 C wasadded triethylamine (86 g, 851.2 mmol) and mesyl chloride (39 g, 340.48 mmol) dropwise.The mixture was stirred at room temperature for 12 h. The reaction was quenched with water(100 mL) and extracted with DCM (100 mL x 2). The combined organic layers were driedover anhydrous Na2SO4, filtered and concentrated in vacuo to give the title compound (47 g,99%) as a brown oil. ?H NMR (400 MHz, CDCI3) 6 5.35 - 5.27 (m, 1H), 4.05 - 3.83 (m, 4H),3.04 (s, 3 H), 2.28 - 2.20 (m, 2 H).
99%	With triethylamine; In dichloromethane; at 0 - 20℃; for 12h;	To a solution of(R)-tetrahydrofuran-3-ol (25 g, 253.7 mmol) in DCM (250 mL) at 0 Cwas added triethylamine (119 mL, 851.2 mmol) and mesyl chloride (39 g, 340.48 mmol)dropwise. The mixture was stirred at room temperature for 12 h. The reaction was quenchedwith water (100 mL) and extracted with DCM (100 mL x 2). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the title compound (47 g, 99%) as a brown oil. ?HNMR (400 IVIFIz, CDC13) 5.35 - 5.27 (m, 1H), 4.05 -3.83 (m, 4H),3.04 (s, 3 H), 2.28 -2.20 (m, 2 H).

95.3%	With triethylamine; In dichloromethane; at 0 - 20℃; for 1h;	Preparation of (R)-tetrahydrofuran-3-yl methanesulfon te (41 4) 41 4 To a solution of (R)-tetrahydrofuran-3-ol (500.00 mg, 5.68 mmol, 1.00 eq) in DCM (5 mL) were added TEA (1.15 g, 11.36 mmol, 2.00 eq) and methanesulfonyl chloride (650.11 mg, 5.68 mmol, 1.00 eq) at 0C. The mixture was stirred at 20C for 1 hr. The mixture was diluted with water (20 mL) and extracted with DCM (10 mL*2). The combined organic layers were concentrated to give 41_4 (900.00 mg, 5.42 mmol, 95.3% yield) as a colorless liquid. NMR (CDCb, 400 MHz) delta 5.33-5.30 (m, 1H), 4.06-3.90 (m, 4H), 3.05 (s, 3H), 2.28-2.23 (m, 2H).
90%	With triethylamine; In dichloromethane; at 25℃; for 3h;	To a solution of (R)-tetrahydrofuran-3-oI (1.50 g, 17.0 mmol) and TEA (3.43g, 34.0 mmol) in DCM (10 mL) was added MsCI (2.54 g, 22.1 mmol) at 0 C. The reaction mixture was stirred at room temperature for 3 hours, then diluted with H20 (30 mL), extracted with DCM (30 mL x 2). The combined organic layers were concentrated to give the title compound (2.5 g, 90 %)as a yellow oil.1H-NMR (ODd3, 400 MHz): oe 5.32 (br, IH), 4.05-3.88 (m, 4H), 3.05 (s, 3H), 2.27-2.23 (m,2H).
88%	With triethylamine; In dichloromethane; at 20℃; for 1h;Cooling with ice;	To a solution of (R)-tetrahydrofuran-3-ol (600 mg, 6.82 mmcl) and TEA (3.07 g, 20.5 mmol) in DCM (10 mL) was added MsCI (1.17 mg, 10.2 mmol) with ice-bath. The solution waswarmed to room temperature and stirred for I h. The mixture was diluted with H20 (40 mL) and extracted with DCM (20 mLx 3). The combined organic layers were dried over Na2SO4, filtered and concentrated to give the desired product (1 g, yield 88%) as a brown oil.1H NMR (300 MHz, CDCI3): 65.32-5.29 (m, 1H), 4.33-3.86 (m, 4H), 3.03 (s, 3H), 2.26-2.19 (m, 2H).
86.4%	With triethylamine; In dichloromethane; at 0℃; for 2h;	Preparation 28; Methanesulfonic acid (R) - (tetrahydrofuran-3 -yl) ester; A solution of 4.86 g (55.18 mmol) of (R)-(-)-3- hydroxytetrahydrofuran m 55 mL of anhydrous DCM (IM) was cooled to 00C with an ice bath. Then 8.5 mL (60.7 mmol, 1.1 eq . ) of triethylamme and 4.8 mL (60.7 mmol, 1.1 eq.) of methanesulfonyl chloride were added successively. The reaction mixture was stirred for 2 hours at 00C and quenched with a saturated solution of sodium bicarbonate (70 mL) . The aqueous layer was extracted with DCM (50 mL) . Then the organic layers were washed with water (2 x 50 mL) , brine (50 mL) and dried over sodium sulfate. After filtration and concentration m vacuo, a yellowish oil (7.93 g, 86.4%) was obtained corresponding to the methanesulfonic acid (R) - (tetrahydrofuran-3 -yl) ester. IH NMR (400 MHz, DMSO-dJ: delta [ppm] 5.26 (m, IH), 3.84-3.67 (m, 4H), 3.18 (s, 3H), 2.22-2.13 (m, IH), 2.08-2.01 (m, IH).
70%	With triethylamine; In dichloromethane; at 0℃; for 3h;	To a solution of (R) -tetrahydrofuran-3-ol (9.1 mL, 114 mmol) in dichloromethane (DCM) (100 mL) at -10 C. in a brine ice bath, triethylamine (23 mL, 170 mmol) was added,Subsequently, methanesulfonyl chloride (9.7 mL, 125 mmol) was added dropwise by syringe so that the internal temperature did not exceed 0 C. The reaction was stirred at 0 C. for 3 hours. Water (15 mL) was added and the mixture was stirred for 5 minutes. A saturated aqueous sodium bicarbonate solution was then added. The layers were separated and the aqueous phase was extracted with DCM. The combined organic extracts were washed with water, diluted with HCl then NaHCO 3, dried over MgSO 4, filtered through a pad of silica gel, the filtrate was concentrated to give the product (15.8 g, 84% yield). )
47%	With triethylamine; In dichloromethane; at 20℃;Cooling with ice;	Example 16. l-(4-(4-amino-l-((»S)-tetrahydrofuran-3-yl)-lH-pyrazolo[3,4-^pyrirmdin- 3-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea (AD66); Step .[0190] (i?)-tetrahydrofuran-3-yl methanesulfonate. A solution of (i?)-tetrahydrofuran-3- ol (1.1 g, 12.5 mmol) and triethylamine (13.6 mL, 97.5 mmol) in CH2Cl2 was cooled in an ice-water bath. To this, methanesulfonyl chloride (3.0 mL, 39 mmol) diluted in CH2Cl2 (10 mL) was added dropwise. The reaction was left stirring for 12 hours at room temperature. Water was added, and organic phases extracted in CH2Cl2 (3x 50 mL), which were subsequently dried onto silica and purified by silica gel chromatography (50% EtOAc:Hexanes to 100% EtOAc gradient) to afford (i?)-tetrahydrofuran-3-yl methanesulfonate (0.97g, brown oil, 47% yield).
	With triethylamine; In dichloromethane; at 20℃; for 2h;Cooling with ice;	R)-Tetrahydrofuran-3-ol 1a (300 mg, 3.40 mmol) and triethylamine (687 mg, 6.80 mmol) were dissolved in 20 mL of dichloromethane in an ice bath, followed by addition of methanesulfonyl chloride (468 mg, 4.10 mmol). The reaction solution was warmed up to room temperature and stirred for 2 hours. The reaction solution was added with 10 mL of dichloromethane, washed with water (30 mLx3), dried with anhydrous magnesium sulphate and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (R)-tetrahydrofuran-3-yl methanesulfonate 1b (520 mg) as a yellow oil, which was directly used in the next step without further purification.
	With triethylamine; In dichloromethane; at 20 - 30℃; for 2h;Cooling with ice; Inert atmosphere;	(R)-Tetrahydrofuran-3-ol 1a (300 mg, 3.40 mmol) and triethylamine (687 mg, 6.80 mmol) were dissolved in 20 mL of dichloromethane in an ice bath, followed by addition of methanesulfonyl chloride (468 mg, 4.10 mmol). The reaction solution was warmed up to room temperature and stirred for 2 hours. The reaction solution was mixed with 10 mL of dichloromethane, washed with water (30 mL×3), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (R)-tetrahydrofuran-3-yl methanesulfonate 1b (520 mg) as a yellow oil, which was directly used in the next step without further purification.
1 g	With triethylamine; In dichloromethane; at 20℃; for 4h;Cooling with ice;	To a solution of (R)-tetrahydrofuran-3-ol (0.5 g) and TEA (1.7 mL) in DCM (10 mL) was added MsCI (0.5 mL) under an ice-water bath. The reaction mixture was stirred at RT for 4 hours. Water (100 mL) was added. The organic layer was separated, dried over sodiumsulfate, filtered and concentrated to afford (R)-tetrahydrofuran-3-yl methanesulfonate (1.0 g) as a yellow oil.
	With triethylamine; In dichloromethane; at 20℃; for 3h;Cooling with ice;	In an ice-water bath, Compound 1a (0.20 g, 2.27 mmol) was dissolved in 20 DCM (6 mL) and the solution was added with TEA (Et3N, 1 mL, 7.19 mmol) and with 23 MsCI (0.39 g, 3.42 mmol) slowly. The mixture was stirred at room temperature for 3 h and spin-dried. The residue was dissolved in 24 EtOAc (60 mL) and washed with water, saturated sodium carbonate and saturated salt solution, then dried over anhydrous sodium sulfate, filtered and spin-dried to give 0.36g crude product.

Reference： [1]Patent: TW2017/8221,2017,A .Location in patent: Page/Page column 105; 106; 107
[2]Patent: WO2016/86200,2016,A1 .Location in patent: Page/Page column 145; 146
[3]Patent: WO2017/205538,2017,A1 .Location in patent: Page/Page column 86
[4]Patent: WO2017/21969,2017,A1 .Location in patent: Page/Page column 38
[5]Patent: WO2018/137593,2018,A1 .Location in patent: Page/Page column 181; 182
[6]Patent: WO2017/12576,2017,A1 .Location in patent: Page/Page column 211
[7]Patent: WO2007/143847,2007,A1 .Location in patent: Page/Page column 137
[8]Patent: JP6557436,2019,B1 .Location in patent: Paragraph 0530; 0531; 0532
[9]Patent: WO2010/45542,2010,A2 .Location in patent: Page/Page column 69
[10]Journal of the American Chemical Society,1993,vol. 115,p. 801 - 803
[11]Journal of Medicinal Chemistry,1993,vol. 36,p. 2300 - 2310
[12]Patent: EP2803664,2014,A1 .Location in patent: Paragraph 0108; 0109
[13]Patent: US2015/5282,2015,A1 .Location in patent: Paragraph 0143; 0144
[14]Patent: WO2015/181186,2015,A1 .Location in patent: Page/Page column 128
[15]Patent: EP3492467,2019,A1 .Location in patent: Paragraph 0063; 0064

5
(S)-3-(trichlorosilyl)tetrahydrofuran [ No CAS ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 2335 - 2338

6
[ 871345-31-2 ]
[ 86087-24-3 ]
[ 871345-46-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5344 - 5352

7
[ 871345-35-6 ]
[ 86087-24-3 ]
[ 871345-48-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5344 - 5352

8
[ 951794-18-6 ]
[ 86087-24-3 ]
[ 951794-31-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 20℃; for 14h;	After adding 0.022 ml of (R)-(-)-3-hydroxytetrahydrofuran, 89.3 mg of triphenylphosphine and 0.155 ml of diethyl azodicarboxylate (hereinafter, ?DEAD?) (2.2 M toluene solution) to a 1 ml THF solution containing 100 mg of {2-(3-hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester at 0 C., the mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated, and the residue was crudely purified by silica gel column chromatography (ethyl acetate-heptane) to give 121 mg of a crude product. Next, 22.5 mg of 2-hydrazinopyrimidine and 0.028 ml of triethylamine were added to a 1 ml DMF solution containing 121 mg of the obtained crude product, and the mixture was stirred at 85 C. for 11 hours under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue was dissolved in 0.8 ml of methanol, 0.8 ml of THF and 0.1 ml of acetic acid. Next, 100 mg of sodium cyanotrihydroborate was added to the solution and the mixture was stirred at room temperature for 2 hours. The reaction mixture was crudely purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give a crude product. To a solution of the obtained crude product in 3 ml of a methanol:water:acetic acid=1:1:1 mixed solvent there was added 100 mg of iron powder, and the mixture was stirred at 65 C. for 14 hours under a nitrogen atmosphere. After filtering the reaction mixture, it was purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give the title compound (20.75 mg) as a light yellow solid. 1H-NMR (CD3OD) delta 1.93 (s, 3H) 1.95-2.09 (m, 1H) 2.11-2.24 (m, 1H) 3.74 (s, 3H) 3.77-3.94 (m, 4H) 4.90-4.99 (m, 1H) 5.62 (s, 1H) 6.39 (t, J=2.0 Hz, 1H) 6.68 (s, 1H) 6.74 (s, 1H) 6.86 (d, J=8.8 Hz, 2H) 7.32 (t, J=4.8 Hz, 1H) 7.60 (d, J=8.8 Hz, 2H) 8.77 (d, J=4.8 Hz, 2H) Mass spectrum (ESI) m/z: 503 (M+H)+

Reference： [1]Patent: US2008/15199,2008,A1 .Location in patent: Page/Page column 39

9
[ 376601-44-4 ]
[ 86087-24-3 ]
(4-cyano-phenylamino)-{3-ethoxy-2-fluoro-5-[(S)-tetrahydro-furan-3-yloxy]-phenyl}-acetic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5357 - 5369

10
[ 553669-04-8 ]
[ 86087-24-3 ]
[ 553669-06-0 ]

Yield	Reaction Conditions	Operation in experiment
69%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 2.5h;	Example 38 3-Cyclohexyl-6-{2-methoxy-4-[(3S)-tetrahydro-3-furanyloxy]phenyl}-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one To a 10 ml tetrahydrofuran suspension of 150 ml (0.423 mmol) of the compound obtained in Example 36, 133 mg (0.508 mmol) of triphenylphosphine, 51 mul (0.635 mmol) of (R)-(-)-3-hydroxytetrahydrofuran, and 80 mul (0.508 mmol) of diethyl azodicarboxylate were slowly added at room temperature, and the mixture was stirred at room temperature for 1 hour.. Further, 44 mg (0.169 mmol) of triphenylphosphine, 17 mul (0.212 mmol) of (R)-(-)-3-hydroxytetrahydrofuran, and 27 mul (0.169 mmol) of diethyl azodicarboxylate were added, and the mixture was stirred at room temperature for 1.5 hours.. Then, the reaction mixture was diluted with ethyl acetate, and the dilution was washed with water and a saturated aqueous solution of sodium chloride in this order.. The washed system was dried over sodium sulfate, and then the solvent was distilled off under reduced pressure.. The residue was purified by silica gel column chromatography (hexane/ethyl acetate = 1/1?1/2) to obtain 124 mg (69%) of the captioned compound.

Reference： [1]Patent: EP1454897,2004,A1 .Location in patent: Page 37

11
[ 636-93-1 ]
[ 86087-24-3 ]
[ 460080-69-7 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 16h;	To a mixture of <strong>[636-93-1]2-Methoxy-5-nitrophenol</strong> (1.69 g, 10 mmol), [TRIPHENYLPHOSPHINE] (5.24 g, 20 mmol) and [3- (R)-HYCLIOXYTETRAHYDROFIUAN] (1.80 g, 20 mmol) in anhydrous tetrahydrofuran (40 [ML)] was added drop-wise, with stirring, diisopropylazodicarboxylate (4.0 [ML,] 20 mmol) and the mixture was allowed to stir at room temperature for 16 h. The mixture was diluted with ether (150 [ML)] and washed with 2N [NAOH] (3 x 50 mL) and brine (50 mL), [(MGS04)] and concentrated in vacuo. The crude residue was purified by flash column chromatography over silica gel (Biotage Flash 40M) eluting with 20% ethyl acetate in hexanes to give 1.05 g of product

Reference： [1]Patent: WO2004/9552,2004,A1 .Location in patent: Page 53

12
[ 621-59-0 ]
[ 86087-24-3 ]
[ 784189-74-8 ]

Yield	Reaction Conditions	Operation in experiment
66%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 5 - 20℃; for 16.1667h;	3-Hydroxy-4-methoxybenzaldehyde (7.6 g; 50 mmol) was dissolved in THF (200 mL) followed by addition of (S)-3-hydroxytetrahydrofuran (6.0 mL; 75 mmol) and triphenylphosphine (19.7 g; 75 MMOL). The resulting solution was cooled to 5 C and diisopropyl azodicarboxylate (14. 8 mL; 75 mmol) was added dropwise over 10 minutes. The clear orange solution was stirred at ambient temperature for 16 hours. Thin layer chromatography analysis using a 1 : 1 MIXTUREAOF HEXANE/ETHYL acetate determined the reaction to be complete. The solvent was removed under reduced pressure and the residue was taken in ethyl acetate (60 mL) and extracted twice with 20% aqueous sodium bisulfite (150ML/EXTRACTION). The extracts were pooled and washed with ethyl acetate (75 mL). The aqueous layer was basified with solid sodium hydroxide (26 g) and then extracted with 3 x 150 mL of ethyl acetate (150 ML/EXTRACTION). The organic extracts were pooled, washed with 40 mL of brine, dried (NA2S04), and concentrated to afford 7.4 g (66%) of a pale yellow OIL. H NMR (CDC13 ; 300 MHz) 8 2. 2-2. 4 (m, 2H); 3.8-4. 1 (m, 7H); 5.0 (m, 1H); 7.0 (d, 1H) ; 7.4 (s, 1H) ; 7.5 (d, 1H) ; 9.9 (s, 1H). ES-MS [M+H] +=223.

Reference： [1]Patent: WO2004/94411,2004,A1 .Location in patent: Page 103

13
4-(2-fluoro-4-methanesulfonyl-phenoxy)-5-methyl-6-(piperidin-4-yloxy)-pyrimidine [ No CAS ]
[ 86087-24-3 ]
4-[6-(2-fluoro-4-methanesulfonyl-phenoxy)-5-methyl-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid (R)-tetrahydro-furan-3-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%		To a solution of 1,1'-carbonyldiimidazole (54.8 mg, 0.338 mmol) in 1 mL THF was added (R)- (+)-3-HYDROXYTETRAHYDROFURAN (32 U. L, 0.38 mmol). After stirring for 30 minutes at room temperature, 1 mL triethylamine, 1 mL THF, and 4- (2-fluoro-4-methanesulfonyl-phenoxy)-5-methyl- 6- (piperidin-4-yloxy)-pyrimidine (70 mg, 0.166 mmol) were added. The resulting mixture was stirred at 60C for 48 hours and purified by HPLC to give Compound C177 as a white solid (35.3 mg, 42%). H NMR (CDC13,400 MHz) 8 1.81-1. 88 (M, 2H), 1.96-2. 09 (M, 3H), 2.12-2. 20 (M, 4H), 3.10 (s, 3H), 3.42-3. 48 (M, 2H), 3.75-3. 81 (M, 2H), 3.84-3. 97 (M, 4H), 5.27-5. 31 (M, 1H), 5.34-5. 38 (M, 1H), 7.41- 7.45 (M, 1H), 7.77-7. 82 (M, 2H), 8.20 (s, 1H). Exact mass calculated for C22H26FN307S 495.15, found 496.3 (MH+).

Reference： [1]Patent: WO2005/7647,2005,A1 .Location in patent: Page/Page column 211

14
methyl-2,3-dideoxy-4,6-O-methylene-D-erythro-hex-2-enopyranoside [ No CAS ]
[ 86087-24-3 ]
[ 861855-11-0 ]
C₁₁H₁₆O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Montmorillonite K10; In dichloromethane; at 40℃; for 1.5h;Product distribution / selectivity;	e) Transacetalisation witla (R)- ()-3-laydroxytetrahydrofuran; OH sOH -D-- (R) t) > 0 X0 I"o i O + MeOH O O Montmorillonite K10 0 The methyl-2,3-unsaturated-4, 6-0-methylene glycoside, (0.1 g, 0. 581 mmol), (R)- (-)-3- hydroxytetrahydrofuran (0.077 g, 0. 871 mmol, 1.5 equivalents) and Montmorillonite K10 catalyst (0.05 g, 50 wt%) were combined under nitrogen and CH2Cl2 (1 ml) added. The reaction was heated at 40C and monitored by GC. After 1.5 hours a slight nitrogen flow was passed over the top of the reaction to remove the CH2Cl2 and MeOH as an azeotrope and the reaction heated for a further 1 hour. Ether was then added and the mixture filtered through Celite. The filtrate was then passed through a small plug of silica to remove the green colouration which had formed and the ether evaporated in vacuo. Mass of the transacetalisation adduct obtained: 77 mg. Cooling of the viscous oily product caused it to crystallise. Remained as a crystalline solid at room temperature. 13C NMR (see example 9(d) above).

Reference： [1]Patent: WO2005/70911,2005,A1 .Location in patent: Page/Page column 63

15
[ 383865-57-4 ]
[ 86087-24-3 ]
[ 1027520-79-1 ]

Yield	Reaction Conditions	Operation in experiment
33%		EXAMPLE 10 (R)-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid tetrahydro-furan-3-yl ester Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and (R)-tetrahydro-furan-3-ol, the title compound was obtained as white crystals (33% yield). MS: m/e=380(M+H+), mp 198-200 C.

Reference： [1]Patent: US2004/235842,2004,A1 .Location in patent: Page 9

Yield	Reaction Conditions	Operation in experiment
77%		EXAMPLE 5 Preparation of (R)-3-hydroxytetrahydrofuran To a solution of (S)-3-hydroxytetrahydrofuran (5 g) having e.e. >99% in CH2Cl2 (100 ml) MsCl (7.8 g) is added and subsequently at 0-5 C. triethylamine (7 g). The temperature is then left to rise up to r.t. and after 1 h is extracted with H2O. The organic phase is concentrated, gives an oil that is then treated with H2O (0.1 L) and CH3SO3H (10.9 g). After heating at 88-90 C. for 5h the mixture is cooled at r.t. and diluted with H2O (50 ml). The obtained solution is eluted on IRA 410 (OH-form) (0.3 L) and the elude gives after concentration under vacuum (R)-3-hydroxytetrahydrofuran with 88% e.e. (yield 77%).
75%		EXAMPLE 2 Preparation of (R)-3-hydroxy-tetrahydrofuran. Operating as in example 1, but using 2.7 g of (S)-3-mesyloxy-tetrahydrofuran prepared starting from (S)-3-hydroxy-tetrahydro-furan, with >=99% e.e., (R)-3-hydroxy-tetrahydrofuran was obtained with a rotatory power of [a]D25-17.1 (c=2.5%, CH3OH), e.e. 97%, with a 75% yield.
		With stirring, 5.0 g of sodium hydroxide dissolved in 5 ml of water was added to the above ester solution, followed by stirring for 3 hours. After distilling off the solvent, the resulting residue was dissolved in diethyl ether, and insoluble materials were removed by filtration. By distilling off the solvent, 4.50 g of crude (R)-(-)-3-hydroxytetrahydrofuran was obtained.

17
[ 42890-76-6 ]
[ 106-97-8 ]
[ 86087-24-3 ]

Yield	Reaction Conditions	Operation in experiment
54%	With CH3SO3H; In water;	EXAMPLE 4 Preparation of (R)-3-hydroxytetrahydrofuran To a mixture of (S)-1,2,4-trimesyloxy butane (10 g), prepared as in HETEROCYCLES vol.24 N 5, 1986 p.1331, starting from <strong>[42890-76-6](S)-1,2,4-butanetriol</strong> having e.e. >99%, in H2O (200 ml) CH3SO3H (5.6g) is added. The temperature is left to rise up to 80 C. and kept for 27h. After cooling to r.t. the mixture is treated in batch with IRA 410 (OH-form) (0.2 L). The resin is filtered off, and washed with H2O; the filtrate gives, after distillation and chromatographic purification (R)-3-hydroxytetrahydrofuran with 94% e.e. (yield 54%).

Reference： [1]Patent: US2003/32818,2003,A1

18
[ 636-93-1 ]
[ 86087-24-3 ]
[ 2446-83-5 ]
2-Methoxy-5-nitro-1-((3R)-tetrahydrofuryloxy)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; In tetrahydrofuran;	EXAMPLE 1B 2-Methoxy-5-nitro-1-((3R)-tetrahydrofuryloxy)benzene To a mixture of <strong>[636-93-1]2-Methoxy-5-nitrophenol</strong> (1.69 g, 10 mmol), triphenylphosphine (5.24 g, 20 mmol) and 3-(R)-hydroxytetrahydrofuran (1.80 g, 20 mmol) in anhydrous tetrahydrofuran (40 mL) was added drop-wise, with stirring, diisopropylazodicarboxylate (4.0 mL, 20 mmol) and the mixture was allowed to stir at room temperature for 16 h. The mixture was diluted with ether (150 mL) and washed with 2N NaOH (3*50 mL) and brine (50 mL), (MgSO4) and concentrated in vacuo. The crude residue was purified by flash column chromatography over silica gel (Biotage Flash 40M) eluding with 20% ethyl acetate in hexanes to give 1.05 g of product The following compounds were prepared in a similar manner as described above:

Reference： [1]Patent: US2002/151566,2002,A1

19
[ 75-44-5 ]
[ 86087-24-3 ]
[ 193415-63-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	In dichloromethane; toluene; at 20℃;	A stirred solution of (i?)-tetrahydrofuran-3-ol (7.9 g, 90 mmol) in anhydrousCH2CI2 (50 mL) under an N2 atmosphere was cooled in an ice bath, and a 20% solution ofphosgene in toluene (134 mL, 270 mmol) was slowly added. The reaction was allowed to warmto room temperature overnight, and the solvent was removed under vacuum to afford (R)-tetrahydrofuran-3-yl chloroformate (12.1 g, 85%) as a clear liquid.
	In toluene;	a Chloroformic Acid 3(R)-tetrahydrofuranyl Ester 12.5 ml (24.15 mmol) of a 20% solution of phosgene in toluene are cooled in an ice-bath, a solution of 1.06 g (12.03 mmol) of (R)-(+)-3-hydroxytetrahydrofuran (JPS CHIMIE, Bevaix, Switzerland) in a small amount of toluene is then added dropwise and, after the mixture has been stirred at RT for 2 h, the excess phosgene is expelled with argon. After concentration by evaporation in a rotary evaporator under reduced pressure, the crude title compound is further processed without being further purified.

Reference： [1]Patent: WO2006/28904,2006,A1 .Location in patent: Page/Page column 186
[2]Patent: US5643878,1997,A

20
[ 125605-10-9 ]
[ 86087-24-3 ]

Yield	Reaction Conditions	Operation in experiment
99.1%	With hydrogenchloride; sodium hydroxide; In methanol; water;	EXAMPLE 5 Preparation of (R)-3-Hydroxytetrahydrofuran To 35 g (0.28 mol) of the (R)-4-chloro-1,3-butanediol obtained in Reference Example 2 hereinafter given was added 70 ml of 0.5N hydrochloric acid, followed by heating under reflux for 2 hours. After cooling, the reaction mixture was neutralized with a 50% aqueous solution of sodium hydroxide, and water was evaporated under reduced pressure. To the residual mixture of crystals and an oily substance was added 60 ml of methanol, followed by stirring. The crystals were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was distilled under reduced pressure to give 16.6 g of the title compound as a colorless substance (purity: 99.1%; yield: 67%). Optical rotation: [alpha]D23 =-15.91 (c=2.45, methanol)
88%	In toluene; for 16h;Heating / reflux;	Example 4; [66] 800 mL of toluene was added to 218 g (1.758 mol) of (No.)-4-chloro-l,3-butanediol prepared in Example 3, and stirring was performed for 16 hours under reflux. The reaction mixture was cooled to room temperature and, after adding 37.3 g (0.352 mol) of Na2CO3 and 1 g (0.055 mol) of water, stirring was further performed for 30 minutes. After removing solid by filtering, the solvent was recovered by concentration under reduced pressure, and the residue was further distilled under reduced pressure. 137 g of colorless (/?)-3-hydroxytetrahydrofuran was obtained (yield = 88%, overall yield = 85%, optical purity = 99.52% ee).
73.62 g	With hydrogenchloride; for 2h;Reflux;	Dilute hydrochloric acid (17.5 ml of conc. hydrochloric acid diluted with 332.50 ml of water) was added to (R)-4-chloro-1,3-butanediol (175 g) and stirring was performed for 2 hours under reflux. After completion of the reaction monitored by gas chromatography, the reaction mixture was cooled to 0 to 5C followed by a pH adjustment between 7 to 8 by using aqueous sodium hydroxide solution (82.5 g of sodium hydroxide dissolved in 165 ml of water). The resulting reaction mass was diluted with methanol (525 ml) followed by distillation under reduced pressure maintaining temperature below 45C. Water was completely removed using methanol stripping (2 x 525 ml) followed by addition of methyl tert-butyl ether (525 ml) to the concentrated mass. The resulting suspension was stirred for 30 minutes followed by filtration to remove inorganic materials. The solid cake was washed with methyl tert-butyl ether (100 ml) followed by distillation under reduced pressure maintaining temperature below 40C to obtain a crude oil (88.46 g). The resulting crude material was distilled under reduced pressure at 90 to 95C (5 mmHg pressure) to give pure (R)-tetrahydrofuran-3-ol as an oil (73.62 g, 59.47 %).1H-NMR: (400 MHz, CDC13): oe: 4.44-4.45 (m, 1H), 3.90-3.97 (m, 1H), 3.69-3.80 (m, 2H), 3.02-3. 12 (brs, 1H), 2.00-2.08 (m, 1H), 1.84-2.00 (m, 1H)Mass [M+Hj: 88.81 Purity by GC: 99.43% areaSpecific optical Rotation (C= 1, Methanol): -17.57

Reference： [1]Patent: US5780649,1998,A
[2]Patent: WO2008/93955,2008,A1 .Location in patent: Paragraph 65-66
[3]Patent: WO2016/21192,2016,A1 .Location in patent: Paragraph 0085

21
[ 905286-30-8 ]
[ 86087-24-3 ]
6-(2-methylphenyl)-2-(methylthio)-8-[(3S)-tetrahydrofuran-3-yl]pyrido[2,3-d]pyrimidin-7(8H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In N,N-dimethyl-formamide; at 0 - 20℃; for 3h;	Example 3b: Synthesis offert-butyl 4-r(6-r2-methylphenylV7-oxo-8-[r3SV tetrahydrofuran-3-yll-7,8-dihydropgammarido[23-^Pyrimidin-2-yliamino')piperidine-l- carboxylate (Compound No. 43) Step a: 6-(2-Methylphenyl)-2-(methyIthio)-8-[(3S)-tetrahydrofuran-3- yl]pyrido[2,3?flpyrimidiii-7(8H)-one; To a solution of compound 6-(2-methylphenyl)-2-(methylthio)pyrido[2,3- ^]pyrimidin-7(8H)-one (Example 3, step d) (2.0 g, 7.06 mmol) in dry dimethyl formamide (10 mL) was added triphenyl phosphine (3.7 g, 14.1 mmol) and R(-)-3 -hydroxy tetrahydrofuran (0.68 g, 7.7 mmol). The mixture was cooled to 0 0C and diisopropyl azadicarboxylate (2.85 g, 14.1 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 3 hours, diluted with ethyl acetate and poured into water. The mixture was then extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The residue thus obtained was purified by column chromatography using ethyl acetate in hexane (3 :7) as eluent to yield the title compound. Yield = 2.0 g.

Reference： [1]Patent: WO2007/36791,2007,A1 .Location in patent: Page/Page column 59

22
N-((1S)-2-[1-(4-fluorophenyl)-1H-indazol-4-yl]oxy}-1-methylethyl)-3,5-dimethyl-1H-pyrazole-4-sulfonamide [ No CAS ]
[ 86087-24-3 ]
N-((1S)-2-[1-(4-fluorophenyl)-1H-indazol-4-yl]oxy}-1-methylethyl)-3,5-dimethyl-1-[(3R)-tetrahydrofuran-3-yl]-1H-pyrazole-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In propyl cyanide; at 120℃; for 2h;	7V-((lS)-2-[l-(4-Fluorophenyl)-lH-indazol-4-yl]oxy}-l-methylethyl)-3,5-dimethyl- lH-pyrazole-4-sulfonamide (0.15 mmol, 66 mg) was mixed with (3R)-tetrahydrofuran-3~yl4-methylbenzenesulfonate (0.20 mmol, 48 mg) in butyronitrile together with cesium carbonate(0.5 mmol, 162 mg). The reaction mixture was stirred and heated at 120C for 2 20 hours. Solvent was removed by evaporation and the residue was dissolved in dichloromethane (20 mL) and washed with IM HCl. The organic layer was dried, concentrated and the residue purified by HPLC-C18.1H NMR (400 MHz, DMSO-^) delta 8.24 (s, IH), 7.83 - 7.69 (m, 3H), 7.43 (t, 2H), 7.34(dd, 2H), 6.57 (d, IH)5 4.92 (septet, IH), 4.02 (dd, IH), 3.94 - 3.86 (m, 3H), 3.76 (td, IH), 2s 3.65 (dd, IH), 3.56 (dd, IH), 2.43 (s, 3H), 2.27 (s, 3H), 2.26 - 2.15 (m, IH), 2.10 (ddd,IH), 1.18 (d, 3H)APCI-MS m/z: 514.4 [MH+].

Reference： [1]Patent: WO2007/46747,2007,A1 .Location in patent: Page/Page column 60

23
[ 939463-48-6 ]
[ 86087-24-3 ]
[ 939463-53-3 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane;	7-Hydroxy-3,3-dimethyl-3,4-dihydronaphthalen-l(2H)-one (0.95 g, 4.99 mmol) was dissolved in 30 ml DCMand triphenylphosphine (1.96 g, 7.49 mmol) and diisopropyl azodicarboxylate (1.23 ml, 6.24 mmol) and (r)-(-)-3-hydroxytetrahydrofuran (0.600 ml, 7.49 mmol) was added. The mixture was stirred over night. 0.5M HCl (aq.) was added and the mixture was extracted 3 times with EtOAc. Glass col. Chrom. (5-30% EtOAc in Hex.) provided (S)-3,3-dimethyl-7-(tetrahydrofuran-3-yloxy)-3,4-dihydronaphthalen- l(2H)-one as a yellow oil. MS m/z: 261.1 (M+l).

Reference： [1]Patent: WO2007/61670,2007,A1 .Location in patent: Page/Page column 158-159

24
[ 108-77-0 ]
[ 86087-24-3 ]
C₇H₇Cl₂N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; tetrabutylammomium bromide; In dichloromethane; water; at 0℃;	Example IV-2: 3-[4-((3i?)-Hydroxymethyl-3,4-dihydro-lJ-7-isoquinolin-2- yl)-6-(tetrahydrofuran-(3i)-yloxy)-[l,3,5]triazm-2-yl]-phenolA mixture of (R)-3-hydroxytetrahydrofuran (717 mg, 8.1 mmol), tetrabutylammonium bromide (260 mg, 0.8 mmol), 50% aqueous sodium hydroxide (8 ml) and dichloromethane (10 ml) was added dropwise at 0C to a solution obtained by dissolving 2,4,6-trichloro-[l,3,5]triazine (1.5 g, 8.1 mmol) in dichloromethane (25 ml). Then, the procedure of Example IV-I was repeated to obtain the title compound (224 mg).1H NMR (300 MHz, CDCl3) delta: 7.99-7.87 (IH, m), 7.70-7.42 (2H, m), 7.33-7.18 (4H, m), 7.05-6.99 (IH, m), 5.67-5.55 (IH, m), 5.40-5.13 (IH, m), 4.81 (2H, dd, J=120Hz, 16.5Hz), 4.21-3.83 (4H, m), 3.73-3.56 (2H, m), 3.10 (IH, dd, J=I 5.3Hz, 5.7Hz), 2.31-2.11 (2H, m).

Reference： [1]Patent: WO2008/72850,2008,A1 .Location in patent: Page/Page column 64

25
[ 897361-59-0 ]
[ 86087-24-3 ]
(R)-6-chloro-4-(tetrahydro-furan-3-yloxy)-pyrido[3,2-d]pyrimidin-2-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%		Examples 22 to 28 - synthesis of 6-benzamido-4-(tetrahvdro-furan-3-yloxy)-Pyridof3.2- c/lpyrimidin-2-ylamines; Various 6-benzamido-4-(tetrahydro-furan-3-yloxy)-pyrido[3,2-c(]pyrimidin-2- ylamines were synthesized according to the general synthetic sequence outlined in Scheme 7.Scheme 7ArB(OH)2, Pd(PPh3)4, K2CO3, DME, H2O Microwave, 1100C, 30 min (ft)-(-)-3-hydroxy-tetrahydrofuran (0.62 ml.) was added to a suspension of NaH (0.31g, 7.7 mmol) in THF (15 ml_). After stirring for 1 hour, the resulting mixture was added to a suspension of N-(4,6-dichloro-pyrido[3,2-c(]pyrimidin-2-yl)-acetamide (0.9 g, 3.5 mmol) in THF (15 ml_). The mixture was stirred at room temperature for 20 minutes, then diluted with EtOAC (10OmL) and washed with brine. The organic layer was dried over Na2SO4 and concentrated to afford 6-chloro-4-(tetrahydro-furan-3-yloxy)-pyrido[3,2- Gf]pyhmidin-2-ylamine as a yellow solid (0.55 g, yield: 51 %) which was characterized by its mass spectrum as follows: MS (m/z) 309.1 [M+H]+.

Reference： [1]Patent: WO2008/77649,2008,A1 .Location in patent: Page/Page column 44

26
[ 75-44-5 ]
[ 6066-82-6 ]
[ 86087-24-3 ]
[ 160333-50-6 ]

Reference： [1]Patent: US6372778,2002,B1 .Location in patent: Example 93

27
[ 752241-81-9 ]
[ 86087-24-3 ]
C₁₉H₂₀O₅S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 3800 - 3809

28
[ 37942-01-1 ]
[ 86087-24-3 ]
[ 1172617-43-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 20℃; for 16h;Nitrogen;	To a stirred solution of 5-bromo-2-methoxyphenol (2.51 g, 12.36 mmol, 1.0 eq) in THF (124 raL, 0.1 M) under N2 at room temperature was sequentially added (/?)-(-)- tetrahydrofuran-3-ol (1.19 mL, 1.30 g, 14.83 mmol, 1.2 eq), PPh3 (5.19 g, 19.78 mmol, 1.6 eq), and DEAD (40 wt % in toluene) (9.0 mL, 8.61 g, 19.78 mmol, 1.6 eq). After stirring at room temperature for 16 h, the reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel using hexanes/EtOAc (3:1) as the eluent to give (S)-(2- methoxyphenoxy)THF 46 (2.59 g, 78%) as a white solid. R/= 0.36 (hexane/EtOAc 3:1); R/= 0.56 (hexane/EtOAc 1 :1). Mp 66-68 C. [alpha]D23 9.8 (c 2.44, MeOH). IR (neat, diamond/ZnSe) 3017, 2977, 2949, 2915, 2855, 1587, 1498, 1467, 1436,1399, 1349, 1322, 1251, 1218, 1182, 1132, 1094, 1065, 1021, 991, 968, 911, 892, 844, 796 cm"1. 1H NMR (400 MHz, ^6-DMSO) delta 7.07-7.09 (m, 2H, aryl), 6.93 (d, IH5 J= 8.2 Hz, aryl), 5.02 (m, IH), 3.71-3.86 (m, 4H), 3.74 (s, 3H, Me), 2.13-2.22 (m, IH), 1.91-1.99 (m, IH). 13C NMR (100 MHz, ^6-DMSO) delta 149.1, 147.5, 123.7, 117.3, 113.9, 111.6, 78.3, 72.1, 66.4, 55.7, 32.3. LC/MS: RT (min) = 5.51; (MH+) 273.0. HRMS: (CI+, m/z), calcd for C, 1H14BrO3 (MH+), 273.0126; found, 273.0127.

Reference： [1]Patent: WO2009/89027,2009,A1 .Location in patent: Page/Page column 58
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 3686 - 3692

29
[ 1118566-69-0 ]
[ 86087-24-3 ]
(S)-3-(2-(4-(5-bromo-2-chlorobenzyl)phenoxy)ethoxy)tetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		To a stirred solution of (i?)-tetrahydrofuran-3-ol (320 mg, 3.63 mmol) in dry tetrahydrofuran (10 mL) was added sodium hydride (145 mg, 3.63 mmol, 60%) slowly under 00C. The reaction was stirred at this temperature for 30 min and then 2-(4-(5-bromo-2- chlorobenzyl)phenoxy)ethyl 4-methylbenzenesulfonate (intermediate AB) (300 mg, 0.61 mmol) was added. The reaction was warmed to room temperature and then heated to reflux overnight. The reaction was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to a yellow oil. The crude oil was purified by flash chromatography to get 200 mg of colorless oil (80% yield).

Reference： [1]Patent: WO2009/26537,2009,A1 .Location in patent: Page/Page column 81

30
[ 876169-01-6 ]
[ 86087-24-3 ]
[ 1192004-98-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3748 - 3756

31
[ 153712-62-0 ]
[ 86087-24-3 ]
[ 1218916-55-2 ]

Yield	Reaction Conditions	Operation in experiment
61.3%	With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; for 4h;	EXAMPLE 13 3-(4-Chlorophenyl)-l-[(3S)-tetrahydrofuran-3-yl]-lH-pyrazolo[4,3-c]pyridineIntermediate 1 (200 mg, 0.87 mmol) and triphenylphosphine (342 mg, 1.31 mmol) were suspended in DCM (5 mL) and (R)-3-hydroxy-tetrahydrofuran (89 muL, 1.31 mmol) and DIAD (257 muL, 1.31 mmol) were added. The reaction mixture was stirred for 4 h and concentrated in vacuo. The residue was purified by reverse phase HPLC (YMC ODS-A 100 x 20 mm, 5 mum, 25 niL/min, gradient 60% to 100% (over 7 min) then 100% (3 min) MeOH in 10% MeOH/water) to give 3-(4-chlorophenyl)-l-[(3S)-tetrahydrofuran-3-yl]-lH- pyrazolo[4,3-c]pyridine (160 mg, 61.3%) as a colourless gum.Analytical HPLC: purity 100% (System B, Rtau = 4.82 min); Analytical LCMS: purity 100% (System B, Rtau = 4.86 min), ES+: 300.5 [35ClMH]+ and 302.5 [37ClMH]+; HRMS calcd for Ci6Hi4ClN3O: 299.0825, found 299.0835.

Reference： [1]Patent: WO2010/31791,2010,A1 .Location in patent: Page/Page column 31-32

32
[ 36082-50-5 ]
[ 86087-24-3 ]
[ 1229186-57-5 ]

Yield	Reaction Conditions	Operation in experiment
41%		Preparation of 5-(4-Isopropoxyphenyl)-N-((ls,4S)-4-methylcyclohexyl)-4-((R)- tetrahydrofuran-3-yloxy)pyrimidin-2-amineStep 1: Preparation of (R)-5-Bromo-2-chloro-4-(tetrahydrofuran-3-yloxy)pyrimidine (1)(DTo a solution of (/?)-(-)-3-hydroxytetrahydrofuran (0.9 g, 10.2 mmol) in 1.2 mL anhydrous THF at O0C was added NaH (60% in mineral oil, 100 mg, 2.5 mmol). The mixture was stirred at O0C for 5 min and then r.t. for 2h until there was no hydrogen bubbles generated. This mixture was added slowly to a solution of 5-bromo-2,4-dichloropyrimidine (570 mg, 2.5 mmol) and (No.)-(-)-3-hydroxytetrahydrofuran (0.1 g, 1.1 mmol) in 0.8 mL THF at -1O0C, and then the reaction mixture was stirred at the same temperature for 30 min. The reaction was quenched with water and extracted with EtOAc. The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The residue was purified using ISCO chromatography (40 g silica gel, 1-20% EtOAc in hexanes in 40 min) to give the title compound (285 mg, 41%) as a white solid. . 1H NMR (CDCl3, 400 MHz) delta 8.45 (s, 1 H), 5.69-5.66 (m, 1 H), 4.11-3.91 (m, 4 H), 2.36-2.21 (m, 2H).

Reference： [1]Patent: WO2010/68863,2010,A2 .Location in patent: Page/Page column 56-58

33
methyl-2,3-dideoxy-4,6-O-methylene-D-erythro-hex-2-enopyranoside [ No CAS ]
[ 86087-24-3 ]
[ 861855-11-0 ]

Reference： [1]New Journal of Chemistry,2010,vol. 34,p. 398 - 402

34
[ 86087-24-3 ]
[ 1258558-36-9 ]

Yield	Reaction Conditions	Operation in experiment
		Example 108A 1-[(3S)-tetrahydrofuran-3-yl]-1H-pyrazol-4-amine The title compound was prepared as described in Example 41A substituting (R)-tetrahydrofuran-3-ol for 1-methylpiperidin-4-ol.

Reference： [1]Patent: US2010/317680,2010,A1

35
[ 1331782-33-2 ]
[ 86087-24-3 ]
[ 1331782-36-5 ]

Yield	Reaction Conditions	Operation in experiment
100%		(R)-Tert-butyl 4-((4-(tetrahydrofuran-3-yloxy)benzo[d]isoxazol-3- yloxy)methyl)piperidine-1-carboxylate (8): To a 20 L glass reactor with the jacket set to 20C were charged (R)-tetrahydrofuran-3-ol (7) (297 g, 3.37 mol) and dimethylacetamide (5.1 L). 2.0 M sodium bis(trimethylsilyl)amide in THF (1.37 L, 2.74 mol) was slowly added via an addition funnel while maintaining a pot temperature less than 30C. The resulting orange/red solution was stirred at 25C for 30 min. Then, tert-butyl 4-((4-fluorobenzo[d]isoxazol-3- yloxy)methyl)piperidine-1 -carboxylate (6) (640.15 g, 1.83 mol) was charged and the reaction mixture was stirred at 25C for 16 h. The reaction mixture was cooled to 20C and water (6.4 L) was slowly added over 45 min maintaining a pot temperature of less than 35C. Ethyl acetate (6 L) was added and the biphasic mixture was stirred for 15 min and then separated. The aqueous layer was back extracted with additional ethyl acetate (4 L). The combined organics were then washed with water (5 L) and a 20% brine solution (5 L). The organic mixture was concentrated under vacuum with the jacket temperature set to 40C to approximately 3 L and held for further processing. Quantitative yield of the desired product, (8) (0.76 Kg, 1 .82 mol), in ethyl acetate was assumed. A sample was pulled and concentrated to dryness for purity analysis. 1 H NMR (400 MHz, CDCI3) delta ppm 1 .25-1.38 (m, 2H), 1 .44 (s, 9H), 1.76-1 .84 (m, 2H), 1 .89-1.97 (b, 1 H), 1 .99-2.12 (m, 1 H), 2.14-2.28 (m, 2H), 2.63-2.84 (m, 2H), 3.90-4.21 (m, 6H), 4.24 (d, J=6.3, 2H), 5.00-5.05 (m, 1 H), 6.48 (d, J=8.2, 1 H), 6.98 (d, J=8.6, 1 H), 7.37 (t, J=8.2, 1 H); LRMS 419.216 (m+1 ).

Reference： [1]Patent: WO2011/101774,2011,A1 .Location in patent: Page/Page column 25; 29
[2]Organic Process Research and Development,2016,vol. 20,p. 233 - 241
[3]Xenobiotica,2016,vol. 46,p. 1112 - 1121

36
[ 86087-24-3 ]
[ 918439-76-6 ]

Yield	Reaction Conditions	Operation in experiment
57%	With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane;Reflux;	[0382] To a solution of (R)-tetrahydrofuran-3-ol (644 mg, 7.31 mmol) in DCM (50 mL) was added sequentially phosphorus triphenyl (3.6 g, 13.89 mmol), glyoxaline (945 mg, 13.89 mmol), and iodine (3.5 g, 13.89 mmol) and the reaction mixture was refluxed overnight. The reaction was then cooled and quenched with a saturated solution of sodium thiosulfate. The organic layers were separated, dried over Na2S04, filtered and evaporated to give a yellow solid which was then triturated with hexanes for 2 hours at room temperature. The mixture was filtered and the filtrate was concentrated to a thin yellow oil which was purified with silica column chromatography eluting with EtOAc/hexanes 0-5% over 30 minutes to give (S)-3-iodotetrahydrofuran as clear oil (824 mg, 57%).

Reference： [1]Patent: WO2011/146287,2011,A1 .Location in patent: Page/Page column 118-119

37
[ 1357075-61-6 ]
[ 86087-24-3 ]
[ 1357075-83-2 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 1640 - 1652

38
[ 1357075-62-7 ]
[ 86087-24-3 ]
[ 1357075-84-3 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 1640 - 1652

39
[ 453-20-3 ]
[ 108-05-4 ]
[ 86087-24-3 ]
[ 86087-23-2 ]
(R)-tetrahydrofuran-3-yl acetate [ No CAS ]
(S)-tetrahydrofuran-3-yl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With EL-14 lipase; In hexane; at 4℃; for 16h;Enzymatic reaction;	General procedure: Lipase enzyme lyophilized powder (2 mg), was added to a solution of the substrate (13.3 mumol) in the reaction solvent (0.5 mL), followed by addition of a solution of vinyl acetate (66.5 mumol) in the reaction solvent (0.5 mL). The reactions were shaken at 150 rpm at 30 C for an appropriate amount of time. The reactions were filtered through anhydrous magnesium sulfate and analyzed directly by chiral GC or evaporated, redissolved in iso-propyl alcohol (HPLC grade) and analyzed by chiral HPLC. The screening results are summarized in Table 2 and Table 3.

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 583 - 586

40
[ 778-29-0 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium osmate(VI) dihydrate; methanesulfonamide; water; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 0℃; for 6h;	To a mixture of K3Fe(CN)6 (8.7 g, 26.6 mmol), K2CO3 (3.7 g, 26.6 mmol), and (DHQ)2-PHAL (0.07 g, 1 mol %), in t-BuOH/H2O (1:1, 60 mL) cooled at 0 C was added K2OsO4·2H2O (0.02 g, 0.2 mol %) followed by the addition of methanesulfonamide (0.84 g, 8.8 mmol). After being stirred for 5 min at 0 C, olefinic tosylate 17 (2 g, 8.8 mmol) was added in one portion. The reaction was stirred at 0 C for 6 h and then quenched with solid sodium bisulfite (1 g). The stirring was continued for an additional 45 min and then the solution was extracted with EtOAc (3 × 30 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure. Silica gel column chromatographic purification of the crude product using petroleum ether/EtOAc (3:2) as an eluent gave alcohol 4 (0.7 g, 95%) as a colorless liquid. [alpha]D20 = +15.4 (c 1, MeOH) {lit.13 [alpha]D20 = +17.6 (c 1, MeOH)}, 89% ee; IR: (CHCl3, cm-1): upsilonmax 1067, 1121, 2878, 2953, 3404; 1H NMR (200 MHz, CDCl3): delta 1.83-1.96 (m, 1H), 2.0-2.18 (m, 2H), 3.76-3.86 (m, 2H), 3.88-4.04 (m, 1H), 4.47-4.52 (m, 1H); 13C NMR (50 MHz, CDCl3): delta 35.3, 66.6, 71.6, 75.4; Anal. Calcd for C4H8O2: C, 54.53; H, 9.15. Found: C, 54.40; H, 9.13.

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 898 - 903

41
[ 1355011-30-1 ]
[ 86087-24-3 ]
[ 1395992-82-1 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃;	To a solution of methyl 6-(2,6-difluoro-4-hydroxyphenyl)-5-fluoropicolinate (1.0 equiv.), (R)-tetrahydrofuran-3-ol (3.0 equiv.) and triphenylphosphine (3.0 equiv.) in THF (0.20 MI at 0 C. was added DIAD (3.0 equiv.) was added. The mixture was stirred at ambient temperature overnight. The reaction mixture was used in next step without workup. LC/MS=353.9 (MH+), Rt=0.88 min.

Reference： [1]Patent: US2012/225062,2012,A1 .Location in patent: Page/Page column 58

42
[ 124811-71-8 ]
[ 86087-24-3 ]
[ 1311255-47-6 ]

Yield	Reaction Conditions	Operation in experiment
65%		To a stirred mixture of <strong>[124811-71-8]4-hydroxy-3-(trifluoromethyl)benzonitrile</strong> (AA2, 9.9 g, 53 mmol) and PPh3 (23.6 g, 90 mmol) in THF (250 mL) at about 0 C, DIAD (17.7 mL ,90 mmol) was added The mixture was stirred for about 10 min. at about 0 C before (R)-(-)-3- hydroxytetrahydrofuran (5 g, 56.7 mmol) in THF (20 mL) was added. The mixture was stirred at ambient temperature overnight under an atmosphere of nitrogen. The solvent was removed in vacuo and the residue was purified by flash column chromatography (EA/petroleum ether = 10-20%) to give (R)-4-(tetrahydrofuran-3-yloxy)-3-(trifluoromethyl)benzonitrile (AA5, 8.8g, 65% yield) which was used without further purification.

Reference： [1]Patent: WO2011/71570,2011,A1 .Location in patent: Page/Page column 169-170

43
[ 86087-24-3 ]
[ 98-59-9 ]
[ 112052-11-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine; In dichloromethane; at 0 - 20℃; for 8h;Product distribution / selectivity;	Step 5: Preparation of (S)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate To a solution of (R)-tetrahydrofuran-3-ol (3 g, 34.1 mmole) and Et3N (6.9 g, 68.2 mmole) in DCM (40 mL) at 0 C. was added 4-methylbenzene-1-sulfonyl chloride (7.2 g, 37.5 mmole. The mixture was stirred at room temperature for 8 h. The mixture was washed with water, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 15% ethyl acetate in hexane) to give the title compound (6.8 g, 83% yield). MS (ESI) m/z: Calc. 242.1 (M+). Found: 243.1 (M++1).

Reference： [1]Patent: US8334292,2012,B1 .Location in patent: Page/Page column 79-80

44
[ 1136962-00-9 ]
[ 86087-24-3 ]
[ 1416157-91-9 ]

Yield	Reaction Conditions	Operation in experiment
26%		Step 1: Preparation of (R)-methyl 2-chloro-5-iodo-6-(tetrahydrofuran-3-yloxy)pyrimidine-4-carboxylate (1) To a solution of (R)-(-)-3-hydroxy-tetrahydrofuran (0.214 g, 2.42 mmol) in anhydrous THF (10 mL) at 0 C. was added NaH (60% in mineral oil, 103 mg, 2.58 mmol). The mixture was stirred at 0 C. for 30 min, then methyl 2,6-dichloro-5-iodopyrimidine-4-carboxylate (0.539 g, 1.62 mmol) was added to the mixture at -10 C. The reaction mixture was stirred at the same temperature for 30 min, and then allow warm to r.t. for 4 h. The reaction was then diluted with EtOAc and acidified with 2 N HCl. The aqueous layer was extracted with EtOAc. The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was dissolved in ether (8 mL) and MeOH (2 mL), and then trimethylsilyldiazomethane (2 M, 2 mL, 4 mmol) was added at 0 C. The reaction was stirred at r.t. for 1 h, and then quenched by 2 N HCl and concentrated in vacuo. The residue was purified by ISCO chromatography (24 g silica gel, 1-10% EtOAc in hexanes in 40 min) to give the title compound (0.140 g, 26%) as a colorless oil. 1H NMR (CDCl3, 500 MHz) delta 5.69-5.66 (m, 1H), 4.10 (dd, 1H), 4.05-3.92 (m, 6H), 2.38-2.30 (m, 1H), 2.24-2.18 (m, 1H).

Reference： [1]Patent: US8334292,2012,B1 .Location in patent: Page/Page column 102

45
[ 555-16-8 ]
[ 86087-24-3 ]
[ 1358604-08-6 ]

Reference： [1]RSC Advances,2013,vol. 3,p. 1695 - 1698

46
[ 53939-30-3 ]
[ 86087-24-3 ]
[ 494771-78-7 ]

Yield	Reaction Conditions	Operation in experiment
47%	With caesium carbonate; In N,N-dimethyl-formamide; at 90℃; for 36h;	To a solution of 5-bromo-2-chloropyridine (10 g, 52.1 mmol) in 100 mL of DMF was added commercially available (R)-(-)-3-hydroxytetrahydrofuran (6.87 g, 78.1 mmol) and Cs2CO3 (33.85 g, 0.104 mol), the resulting mixture was heated 90 C. for 36 hours. The solvent was concentrated and the residue was extracted with EtOAc (500 ml), washed with water (200 ml). The organic layer was dried over Na2SO4, concentrated and purified by chromatography on silica gel (eluting with Petrol ether:EtOAc=100:1) to afford 5-Bromo-2-[(R)-(tetrahydro-furan-3-yl)oxy]-pyridine (5.9 g, yield: 47%) as a solid. 1HNMR (CDCl3 400 MHz): delta 8.15 (d, J=2.4 Hz, 1H), 7.61-7.64 (m, 1H), 6.64 (d, J=8.8 Hz, 1H), 5.47-5.50 (m, 1H), 3.85-4.02 (m, 4H), 2.07-2.28 (m, 2H). [alpha]D20=+18.5 (C=0.189, CHCl3).

Reference： [1]Patent: US2013/12530,2013,A1 .Location in patent: Paragraph 0181

47
[ 2129-31-9 ]
[ 86087-24-3 ]
C₂₃H₂₁O₄P [ No CAS ]
[ 2272-04-0 ]

Reference： [1]Synthesis,2013,vol. 45,p. 931 - 935

48
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1]Synthesis,2013,vol. 45,p. 931 - 935

49
[ 34387-89-8 ]
[ 86087-24-3 ]
[ 1429510-47-3 ]

Yield	Reaction Conditions	Operation in experiment
12.4 g	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 35℃; for 7.71667h;	(2) Synthesis of (S)-t-butyl (1,3-dioxoisoindolin-2-yl)(tetrahydrofuran-3-yl)carbamate DEAD (11.5 mL) was added dropwise to a solution of (R)-(-)-3-hydroxytetrahydrofuran (CAS No. 86087-24-3) (4.84 g), t-butyl (1,3-dioxoisoindolin-2-yl)carbamate (12 g) and triphenylphosphine (18.0 g) in THF (160 mL) under ice-cooling over five minutes. The reaction mixture was stirred at 0 C. for three minutes and then at room temperature for seven hours and 40 minutes. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 20%) to give the title compound (12.4 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 1.29 (s, 6H), 1.53 (s, 3H), 2.12-2.33 (m, 2H), 3.63-3.97 (m, 4H), 4.84-4.94 (m, 0.33H), 5.04-5.14 (m, 0.67H), 7.75-7.84 (m, 2H), 7.87-7.94 (m, 2H). ESI-MS m/z 355 [M+Na]+

Reference： [1]Patent: US2013/143907,2013,A1 .Location in patent: Paragraph 0348; 0349; 0350; 0351

50
[ 1454558-37-2 ]
[ 86087-24-3 ]
[ 1454558-38-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium hydride; In tetrahydrofuran; at 20℃; for 2h;	Part B. 4-(3-Bromo-Dyrazoloil.5-alDyrimiclin-5-yl)-DiDerazine-l-carboxylic acid (R)-(tetrahvdro- furan-3-yl) ester To 112 mg (0.25 mmol) of 4-nitrophenyl 4-(3-bromopyrazolo[l,5-a]pyrimidin-5-yl)piperazine- 1-carboxylate dissolved in 10 ml_ of THF, was added (R)-tetrahydrofuran-3-ol (44 mg, 0.5 mmol), followed by 60% NaH (40 mg, 1.0 mmol) and stirred at RT for 2 hr. After 2 hr it was diluted with 20 ml_ of EtOAc and slowly quench with brine. The organic layer was dried over MgS04 and concentrated, it was purified over 12 gram silica gel column eluting with 0-10% MeOH/DCM to obtain 71 mg (72% yield) of the desired product.

Reference： [1]Patent: WO2013/134228,2013,A1 .Location in patent: Page/Page column 50

51
[ 1309831-35-3 ]
[ 86087-24-3 ]
1-(2-((R)-tetrahydrofuran-3-yloxy)-5-nitrophenyl)-4-methyl-1H-tetrazol-5(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%		(R)-(-)-3-Hydroxytetrahydrofuran (440 mg, 5 mmol, 2 equiv) in THF (15 ml) under argon gas, was cooled to 0 C. Potassium tert-butoxide (617 mg, 5.5 mmol, 2.2 equiv) was added in one portion, and the reaction mixture was stirred for 20 minutes at 0 C. Thenl-(2-fluoro-5-nitrophenyl)-4-methyl-lH-tetrazol-5(4H)-one (Described in: WO 2011/068898. 598 mg, 2.5 mmol, 1 equiv) was added in one portion, and the reaction mixture was stirred for 10 minutes at 0 C and allowed to warm up to ambient temperature over 2 hours. The reaction mixture was concentrated, and the residue was taken in DCM and water. The layers were separated, and the organic layer was washed with water (x2), dried over Na2S04, filtered, and concentrated to provide l-(2-((R)-tetrahydrofuran-3-yloxy)- 5-nitrophenyl)-4-methyl-lH-tetrazol-5(4H)-one (723 mg, 94%) as a yellow solid that was used without further purification. [00568] 1H NMR (300 MHz; 6-DMSO) delta 8.41-8.47 (m, 2H), 7.51-7.54 (d, 1H, J = 9Hz), 5.31-5.4 (t, 1H, J = 3.6Hz), 3.88-3.93 (dd, 1H, J = 4.2Hz, J = 10.5Hz), 3.70-3.74 (m, 3H), 3.62 (s, 3H), 2.20-2.27 (m, 1H), 1.89-1.93 (m, 1H); m/z = 308 (M+H)+.

Reference： [1]Patent: WO2013/152198,2013,A1 .Location in patent: Paragraph 00567; 00568

52
[ 1037093-11-0 ]
[ 86087-24-3 ]
[ 1037093-12-1 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 16.5h;	Example 39: (75R)-2-[(l-Aminoisoquinolin-6-yl)amino]-8-fluoro-4, 15,20-trimethyl-7- [(3 S)-oxolan-3 -yloxy]- 13 -oxa-4, 1 1 -diazatricyclo [14.2.2.16' 1 ]henicosa- l(18),6,8,10(21),16,19-hexaene-3, 12-dione; trifluoroacetic acid 39A: (5)-3-Fluoro-5-((methylamino)methyl)-4-((tetrahydrofuran-3-yl)oxy)aniline dihydrochloride [00391] To a solution of 17D (640 mg, 2.131 mmol), (R)-tetrahydrofuran-3-ol (413 mg, 4.69 mmol) and triphenylphosphine in THF (5 mL) at 0 C, was added diisopropyl azodicarboxylate (0.930 mL, 4.69 mmol) dropwise. The reaction mixture was stirred 0 C for 30 min, and at rt for 16 h. The mixture was concentrated and purified by flash chromatography (0-50% EtOAc in hexanes). The desired fractions were combined, concentrated. The residue was dissolved in MeOH (10 mL) and THF (2 mL). To this solution was added ammonium chloride (2.250 mL, 63.9 mmol) and zinc (0.195 mL, 21.31 mmol). The mixture was stirred at rt for 2 h, concentrated, stirred with sat. a2CC>3 (50 mL) for 20 min, extracted with EtOAc (3x20 mL). The residue was purified by flash chromatography. The desired fractions were concentrated, dissolved in EtOAc (5 mL), and treated with HC1 (4N, 5 mL) for 3 h at rt. The mixture was concentrated to give 39A (630 mg, 2.012 mmol, 94% yield) as a yellow solid. MS (ESI) m/z: 242.2 (M+H)+. 39B: (5)-Benzyl 5-amino-3-fluoro-2-((tetrahydrofuran-3- yl)oxy)benzyl(methyl)carbamate [00392] To 39A (640 mg, 2.043 mmol), NN-diisopropylethylamine (1.424 ml, 8.17 mmol) in DMF (10 ml), was added N-(benzyloxycarbonyloxy) succinimide (560 mg, 2.248 mmol). The mixture was stirred at rt for 1 h, quenched with water, extracted with EtOAc. The organic layer was washed with brine, dried ( a2S04) and concentrated. The crude product was purified by flash chromatography to give 39B (540 mg, 1.442 mmol, 70.6% yield). MS (ESI) m/z: 375.2 (M+H)+. 39C: Benzyl 5-((((R)-2-(4-bromo-2-methylphenyl)propoxy)carbonyl)amino)-3-fluoro-2- -tetrahydrofuran-3-yl)oxy)benzyl(methyl)carbamate [00393] To 39B (540 mg, 1.442 mmol) and NaHC03 (606 mg, 7.21 mmol) in CH2C12 (10 ml) at 0 C, was added phosgene (20% in toluene, 1.518 ml, 2.88 mmol). The mixture was stirred at 0 C for 30 min, rt for 1 h, filtered, and concentrated. The residue in CH2CI2 (10 ml) was added to a solution of Intermediate 5A (330 mg, 1.442 mmol) and TEA (0.393 ml, 2.88 mmol) in CH2C12 (10 ml) at 0 C. The mixture was stirred at rt for 3 h, quenched with water, and extracted with EtOAc. The combined organic layer was washed with IN HC1, brine, dried ( a2S04). The crude product was purified by flash chromatography to yield 39C (777 mg, 1.234 mmol, 86% yield). MS (ESI) m/z: 629.1 (M+H)+. 39D: (4-((R)-l-(((3-((((Benzyloxy)carbonyl)(methyl)amino)methyl)-5-fluoro-4-(((5)- tetrahydrofuran-3-yl)oxy)phenyl)carbamoyl)oxy)propan-2-yl)-3-methylphenyl)boronic acid [00394] To a reaction tube was added 39C (770 mg, 1.223 mmol), 5,5,5',5'- tetramethyl-2,2'-bi(l,3,2-dioxaborinane) (332 mg, 1.468 mmol), KOAc (300 mg, 3.06 mmol), and Pd(dppf)Cl2 (201 mg, 0.245 mmol) in DMSO (10 ml). The tube was filled with Ar, sealed and stirred at 85 C for 2 h. The mixture was quenched with H20, and extracted with EtOAc (3x). The combined organic layers was filtered though silica gel and concentrated. The residue was purified by prep HPLC to give 39D (405 mg, 0.681 mmol, 55.7% yield) as a tan solid. MS (ESI) m/z: 595.4 (M+H)+. 39E: 2-((l-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-yl)amino)-2-(4-((R)-l-(((3- fluoro-5-((methylamino)methyl)-4-(((5)-tetrahydrofuran-3- yl)oxy)phenyl)carbamoyl)oxy)propan-2-yl)-3-methylphenyl)acetic acid [00395] 39D (405 mg, 0.681 mmol), Intermediate 1 (245 mg, 0.681 mmol) and glyoxylic acid monohydrate (50.4 mg, 0.681 mmol) were dissolved in CH3CN (3 ml) and DMF (0.5 ml). The mixture was stirred at 85 C for 20 h, quenched with water, and extracted with EtOAc (3x20 ml). The combined organic layer was washed with IN HC1, brine, dried ( a2S04) and concentrated. The crude was purified by flash chromatography (0-10% MeOH in CH2CI2). The desired fractions were combined and concentrated. The residue was dissolved in MeOH (8 mL). Pd/C was added and the mixture was hydrogenated at 40 psi for 6 h. The mixture was filtered and concentrated gives 39E (298 mg, 0.358 mmol, 52.6% yield). MS (ESI) m/z: 832.2 (M+H)+. 39F: tert-Butyl N-[(tert-butoxy)carbonyl]-N-(6- [(75R)-8-fluoro-4,15,20-trimethyl-3,12- dioxo-7- [(3 S)-oxolan-3 -yloxy] - 13 -oxa-4, 1 1 -diazatricyclo [14.2.2.16> 10]henicosa- 1 (18),6,8, 10(21 ), 16, 19-hexaen-2-yl]amino} isoquinolin- 1 -yl)carbamate [00396] To BOP (317 mg, 0.716 mmol), 4-dimethylaminopyridine (219 mg, 1.791 mmol) in CH2C12 (40 mL), was added a solution of 39E (298 mg, 0.358 mmol) in DMF (10 mL) via a syringe pump over 6 h. The mixture was stirred rt for 16 h, then concentrated and purified by prep HPLC to give 39F (180 mg, 61.7% yield). MS (ESI) m/z: 814.3 (M+H)+. Example 39 [00397] 39F (152 mg, 0.187 mmol) in EtOAc (5 mL) was treated with 4.0 M HC1 in diox...

Reference： [1]Patent: WO2013/184734,2013,A1 .Location in patent: Paragraph 00390; 00391

53
[ 1198319-51-5 ]
[ 86087-24-3 ]
[ 1470082-82-6 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 8834 - 8848

54
(1S,3R,4S,5S,7S)-4-amino-adamantan-1-ol hydrochloride [ No CAS ]
[ 1547489-89-3 ]
[ 86087-24-3 ]
4-cyclopropyl-2-ethoxy-N-(trans-5-hydroxy-2-adamantyl)thiazole-5-carboxamide [ No CAS ]
4-cyclopropyl-N-(trans-5-hydroxy-2-adamantyl)-2-[(3R)-tetrahydrofuran-3-yl]oxythiazole-5-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 970 - 986

55
[ 1547489-89-3 ]
[ 86087-24-3 ]
[ 1547490-73-2 ]
[ 1547490-72-1 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 970 - 986

56
[ 7461-50-9 ]
[ 86087-24-3 ]
[ 1431654-84-0 ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium hydride; In tetrahydrofuran; mineral oil; for 19h;	The reaction was run similarly to the above, with NaH (60% in oil, 227.0 mg, 5.67 mmol), THF (5.4 mL), (R)-tetrahydrofuran-3-ol (0.456 mL, 5.67 mmol), and <strong>[7461-50-9]2-chloro-4-aminopyrimidine</strong> (566.0 mg, 4.36 mmol) for 19 h. Water and EtOAc were added (10 mL each), along with enough saturated aqueous NH4Cl to bring the pH down to 8 (about 2 mL). The layers were separated and the aqueous layer was washed twice more with EtOAc (2x10 mL). The combined organics were washed with brine, dried with Na2SO4, filtered and concentrated to give 748.0 mg of crude product. This was triturated with Et2O and filtered. The solid was washed with Et2O and dried under vacuum to give (R)-2-(tetrahydrofuran-3-yloxy)pyrimidin-4-amine (419 mg, 53%). MS (ESI) calcd for C8H11N3O2: 181.09; found: 182 [M+H].
51.5%		To a stirred solution of (R)-tetrahydrofuran-3-ol (2.72 g, 30.9 mmol) in THF (30 mL) was added NaH (0.926 g, 23.16 mmol) and stirred for 30 min at room temperature. To this <strong>[7461-50-9]2-chloropyrimidin-4-amine</strong> (2.0 g, 15.44 mmol) was added in portions for about 15 min and heated at 70 C. for 16 h. The reaction mixture was allowed to room temperature and subsequently cooled to 0 C., quenched with ice cold water and extracted with ethyl acetate (3×50 ml). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude compound. The crude product was purified by flash column chromatography (silica-gel: 100-200 mesh) to afford (R)-2-(tetrahydrofuran-3-yloxy)pyrimidin-4-amine (1.6 g, 8.839 mmol, 51.5% yield) as an off white solid.
51.5%		To a stirred solution of (R)-tetrahydrofuran-3-ol (2.72 g, 30.9 mmol) in THF (30 mL) was added NaH (0.926 g, 23.16 mmol) and stirred for 30 min at room temperature. To this 2- chloropyrimidin-4-amine (2.0 g, 15.44 mmol) was added in portions for about 15 min and heated at 70 C for 16 h. The reaction mixture was allowed to room temperature and subsequently cooled to 0 C, quenched with ice cold water and extracted with ethyl acetate (3x50 ml). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude compound. The crude product was purified by flash column chromatography (silica-gel: 100-200 mesh) to afford (R)-2- (tetrahydrofuran-3-yloxy)pyrimidin-4-amine (1.6 g, 8.839 mmol, 51.5 % yield) as an off white solid.

Reference： [1]Patent: EP2768509,2017,B1 .Location in patent: Paragraph 0652; 0653
[2]Patent: US2015/152108,2015,A1 .Location in patent: Paragraph 0417; 0418
[3]Patent: WO2016/79709,2016,A1 .Location in patent: Page/Page column 162-163

57
[ 86087-24-3 ]
[ 208173-24-4 ]
1-{4-[(3R)-tetrahydrofuran-3-yloxy]-3-(trifluoromethyl)phenyl}ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1-methyl-pyrrolidin-2-one; water;	Preparation Example 30 To a solution of (3R)-tetrahydrofuran-3-ol (1.0 g) in N-methylpyrrolidone (20 mL) was added a 60% oil dispersion of sodium hydride (430 mg) under ice-cooling, followed by stirring at the same temperature for 10 minutes. To the reaction mixture was added dropwise a solution of <strong>[208173-24-4]1-[4-fluoro-3-(trifluoromethyl)phenyl]ethanone</strong> (2.0 g) in N-methylpyrrolidone (10 mL), and the mixture was stirred for 1 hour under ice-cooling. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The insoluble materials were then separated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 1-{4-[(3R)-tetrahydrofuran-3-yloxy]-3-(trifluoromethyl)phenyl}ethanone (1.84 g) as an oily substance.
1.84 g		To (3R)-tetrahydrofuran-3-ol (1.0g) in N-methylpyrrolidone (20 ml), 60% oil dispersion of sodium hydride under ice cooloing (430 mg) was added, and stirrerd at same temperature for 10 minutes. to this reaction mixture <strong>[208173-24-4]1-[4-fluoro-3-(trifluoromethyl)phenyl]ethanone</strong> (2.0g) in N-methylpyrrolidone (10 ml) was added dropwise, and stirred for 1 hour under ice cooloing. And adding water to a reaction mixture, extracted to ethyl acetic acid. Organic layer water and saturated sodium chloride aqueous solution cleaning and, after dry magnesium sulfate anhydride, insoluble filtration fractionation and, the concentrated or depressurization of the fluid bag for filtrate. Residue silica gel column chromatography (cyclohexan-acetic acid ethyl) for purifying the, 1-{4-[(3R)-tetrahydrofuran-3-yloxy]-3-(trifluoromethyl)phenyl}ethanone (1.84g) obtained as oily substance.

Reference： [1]Patent: EP2963036,2016,A1
[2]Patent: KR2015/120516,2015,A .Location in patent: Paragraph 0377; 0378

58
[ 104711-65-1 ]
[ 86087-24-3 ]
(R)-6-methyl-4-((tetrahydrofuran-3-yl)oxy)-picolinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium hydride; In N,N-dimethyl-formamide; for 18h;	c. SYNTHESIS OF (R)-6-METHYL-4-((TETRAHYDROFURAN-3- YL)OXY)PICOLINONITRILE (COMPOUND 3)To a solution of (R)-tetrahydrofuran-3-ol (693 mg, 7.86 mmol, 2.0 eq) and sodium hydride (199 mg, 7.86 mmol, 2.0 eq) in DMF (20 mL) was added compound 2 (600 mg, 3.93 mmol, 1.0 eq). After 18 hours, the reaction was diluted with EtOAc and washed with water and brine twice. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 325 mg (40%) of the title compound: 1H NMR (400 MHz, , DMSO-d6) delta 7.52 (d, J = 2.28 Hz, 1H), 7.18 (d, J = 2.28 Hz, 1H), 5.22-5.19 (m, 1H), 3.91-3.33 (m, 4H), 2.46 (s, 3H), 2.34-2.25 (m, 1H), 2.00-1.93 (m, 1H); ES-MS [M+1]+: 205.2.

Reference： [1]Patent: WO2015/200682,2015,A1 .Location in patent: Paragraph 00469

59
[ 22929-52-8 ]
[ 86087-24-3 ]

Reference： [1]ACS Catalysis,2016,vol. 6,p. 1598 - 1605
[2]ChemBioChem,2018,vol. 19,p. 239 - 246

60
[ 864070-18-8 ]
[ 86087-24-3 ]
[ 915095-89-5 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4173 - 4184

61
[ 3616-56-6 ]
[ 86087-24-3 ]
[ 115170-40-6 ]
[ 162012-70-6 ]
4-dimethylamino-N-(4-(2,3-dihydroindol-1-yl)-7-(((3R)-tetrahydrofuran-3-yl)oxy)quinolin-6-yl)-2-(4-methylpiperazin-1-yl)but-2-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.7%		Intermediate IV andBromo-2,3-dihydro-1H-pyrrolo (2,3-b) pyridine to give d,React with (S) -3-hydroxytetrahydrofuran,A dark yellow solid VId was obtained.The intermediate d with activated carbon,Ferric chloride and hydrazine hydrate reduction,Obtained as an off-white solid VIId.Then VIId and diethyl phosphoric acid condensation,Compound VIIId is obtained,In the condensation with (dimethylamino) acetaldehyde diethyl acetal,The target compound was obtained. Yield: 48.7percent.

Reference： [1]Patent: CN106831725,2017,A .Location in patent: Paragraph 0164-0166

62
[ 22929-52-8 ]
[ 86087-24-3 ]
[ 86087-23-2 ]

Reference： [1]ChemBioChem,2018,vol. 19,p. 239 - 246
[2]ChemBioChem,2018,vol. 19,p. 239 - 246

63
[ 22717-55-1 ]
[ 86087-24-3 ]
methyl (S)-4-chloro-2-((tetrahydrofuran-3-yl)oxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54.54%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃;	To a stirred solution of <strong>[22717-55-1]methyl 4-chloro-2-hydroxybenzoate</strong> (2.0 g, 10.718 mmol, 1.05 eq) in THF (20 mL) was added (R)-tetrahydrofuran-3-ol (1.88 g, 21.437 mmol, 2.0 eq)followed by triphenylphosphine (5.62 g, 21.437 mmol, 2.0 eq) and diethylazodicarboxylate(5.04 g, 28.940 mmol, 2.7 eq). The reaction mixture was stirred at room temperature forovernight. After completion of the reaction (monitored by TLC), the reaction mixture wasdiluted with EtOAc (200 mL) and washed with water (100 mL). The organic layer was dried10 over Na2S04, filtered and evaporated under reduced pressure. The residue was purified bysilica gel column chromatography by using 0-20% ethyl acetate in hexane gradient. Thefractions containing the expected product were combined and concentrated under reducedpressure to obtain the title compound ( 1.5 g, yield: 54.54%) as a colourless liquid. 1 H NMR(300 MHz, CDCh): 8 ppm 7.76 (d, J = 8.4 Hz, lH), 6.98 (dd, J = 8.4, 1.8 Hz, lH), 6.88 (d, J15 = 1.8 Hz, lH), 5.0-4.93 (m, lH), 4.10-3.85 (m, 7H), 2.24-2.17 (m, 2H); ESI-MS: m/z 256.91(M+Ht.

Reference： [1]Patent: WO2018/29604,2018,A1 .Location in patent: Page/Page column 61

64
[ 51834-97-0 ]
[ 86087-24-3 ]
(S)-2-methoxy-5-(tetrahydrofuran-3-oxo)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.65%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 16h;	Dissolve 1c (1.51 g, 12.07 mmol) in 8 mL of tetrahydrofuran and in turn place (R)-tetrahydrofuran-3-ol 4a (1.17 g, 15.69 mmol) and triphenylphosphine (4.11 g, 15.69 mmol) at 0C. Adding the above solution, diisopropyl azodicarboxylate (3.17 g, 15.69 mmol) was slowly added dropwise, and the mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography using an eluent system C to give the titled product 4b (2 g, colorless oil), yield: 80.65%.

Reference： [1]Patent: CN107793396,2018,A .Location in patent: Paragraph 0263-0266

65
[ 86087-24-3 ]
[ 205055-63-6 ]
(R)-6-bromo-1-((tetrahydrofuran-3-yl)oxy)isoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium hexamethylsilazane; In tetrahydrofuran; at 120℃; for 0.333333h;Microwave irradiation;	(R)-tetrahydrofuran-3-ol (43.6 mg, 0.495 mmol, 1.20 eq) was dissolved in THF (1 mL) and 1M potassium bis(trimethylsilyl)amide in THF (0.495 mL, 0.495 mmol, 1.20 eq) was added followed by <strong>[205055-63-6]6-bromo-1-chloroisoquinoline</strong> (100 mg, 0.412 mmol, 1.00 eq) in THF (1mL). The reaction was heated in a microwave reactor at 120 C for 20 minutes, neutralized with 2N HCl and concentrated. Purification by flash chromatography on silica gel using 0-20% hexanes/ethyl acetate afforded 105 mg (87%) of the title compound as a clear oil: 1H NMR (400 MHz, DMSO-d6) delta 8.19 (s, 1H), 8.08 (d, J = 8.8 Hz, 1H), 8.03 (d, J = 5.9 Hz, 1H), 7.74 (d, J = 8.8 Hz, 1H), 7.36 (d, J = 5.8 Hz, 1H), 5.70 (t, J = 4.3 Hz, 1H), 4.01-3.77 (m, 4H), 2.34-2.25 (m, 1H), 2.16-2.10 (m, 1H); ES-MS [M+1]+: 294.2.

Reference： [1]Patent: WO2018/89546,2018,A1 .Location in patent: Paragraph 0177

66
[ 86087-24-3 ]
[ 151103-08-1 ]
(R)-3-[(tetrahydrofuran-3-yl)oxy]-4-(difluoromethoxy)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a 0 C solution ofPPh3 (723 mg, 2.76 mmol) and (R)- or (S)-3-hydroxytetrahydrofuran(223 muL, 2.76 mmol) in CH2Cl2 (10 mL) was addeddropwise with a syringe a solution of di-tert-butyl azodicarboxylate(636 mg, 2.76 mmol) in CH2Cl2 (5 mL). After 5 min, asolution of compound 2 in CH2Cl2 (5 mL) was addeddropwise with a syringe. The reaction mixture was warmed toroom temperature and stirred for 8 h. After removal of thesolvent, the residue was purified by flash chromatography (5:1hexane/EtOAc) to afford compound (S)- or (R)-3 (0.46 g,96%) as a colorless oil: 1H NMR (400 MHz, CDCl3) delta 9.93 (s,1H), 7.48 (dd, J = 1.6, 8.4 Hz, 1H), 7.44 (d, J = 1.6 Hz, 1H),7.33 (d, J = 8.4 Hz, 1H), 6.67 (t, J = 74.4 Hz, 1H), 5.08-5.06(m, 1H), 4.06-3.91 (m, 4H), 2.31-2.29 (m, 1H), 2.20-2.18(m, 1H).

Reference： [1]Biochemistry,2018,vol. 57,p. 4518 - 4525

67
[ 104711-65-1 ]
[ 86087-24-3 ]
C₁₁H₁₂N₂O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 47 - 50

68
[ 64080-15-5 ]
[ 86087-24-3 ]
(S)-3-(2-bromo-4-ethylphenoxy)tetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropyl (E)-azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;Inert atmosphere;	In a 100 mL flask was added <strong>[64080-15-5]2-bromo-4-ethylphenol</strong> (0.685 g, 3.41 mmol) from Example I-111A and triphenylphosphine (1.429 g, 5.45 mmol) in tetrahydrofuran (16 mL). The mixture was stirred briefly at ambient temperature, under nitrogen, and (E)-diisopropyl diazene-1,2-dicarboxylate (1.073 mL, 5.45 mmol) was added. The mixture was stirred briefly under nitrogen at ambient temperature and (R)-tetrahydrofuran-3-ol (0.3 g, 3.41 mmol) was added dropwise. The reaction mixture was stirred overnight at ambient temperature. The solvent was removed under reduced pressurerude material was purified by chromatography, eluting on 24 g silica gel cartridge with a gradient of 0-30% ethyl acetate/heptanes over a period of 10 minutes to provide the title compound. 1H NMR (501 MHz, chloroform-d) delta ppm 7.39 (d, J=2.1 Hz, 1H), 7.05 (dd, J=8.3, 2.2 Hz, 1H), 6.76 (d, J=8.3 Hz, 1H), 4.92 (ddt, J=6.8, 4.8, 2.4 Hz, 1H), 4.07-3.98 (m, 3H), 3.93 (td, J=8.1, 4.2 Hz, 1H), 2.57 (q, J=7.6 Hz, 2H), 2.26-2.11 (m, 2H), 1.20 (t, J=7.6 Hz, 3H)+ MS (APCI+) m/z 271 (M+H)+.

Reference： [1]Patent: US2019/77784,2019,A1 .Location in patent: Paragraph 2292

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P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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. 86087-24-3 ]

Quality Control of [ 86087-24-3 ]

Related Doc. of [ 86087-24-3 ]

Product Details of [ 86087-24-3 ]

Calculated chemistry of [ 86087-24-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 86087-24-3 ]

Application In Synthesis of [ 86087-24-3 ]

[ 86087-24-3 ] Synthesis Path-Upstream 1~23

[ 86087-24-3 ] Synthesis Path-Downstream 1~68

Related Functional Groups of [ 86087-24-3 ]

Alcohols

Related Parent Nucleus of [ 86087-24-3 ]

Aliphatic Heterocycles

Tetrahydrofurans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 86087-24-3 ]

Related Parent Nucleus of
[ 86087-24-3 ]