[ CAS No. 22323-82-6 ] {[proInfo.proName]}

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2D 3D

Structure of 22323-82-6 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 22323-82-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 22323-82-6 ]

SDS Specification

Alternatived Products of [ 22323-82-6 ]

Product Details of [ 22323-82-6 ]

CAS No. :	22323-82-6	MDL No. :	MFCD00063239
Formula :	C₆H₁₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RNVYQYLELCKWAN-YFKPBYRVSA-N
M.W :	132.16	Pubchem ID :	736057
Synonyms :	S-(+)-2,3-O-Isopropylideneglycerol	Chemical Name :	(S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol

Calculated chemistry of [ 22323-82-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	32.21
TPSA :	38.69 ?2

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) :	-7.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	-0.2
Log Po/w (WLOGP) :	0.13
Log Po/w (MLOGP) :	-0.26
Log Po/w (SILICOS-IT) :	0.84
Consensus Log Po/w :	0.48

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.47
Solubility :	45.1 mg/ml ; 0.341 mol/l
Class :	Very soluble
Log S (Ali) :	-0.16
Solubility :	92.2 mg/ml ; 0.698 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.52
Solubility :	40.1 mg/ml ; 0.303 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.09

Safety of [ 22323-82-6 ]

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 [ 22323-82-6 ]

* 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 [ 22323-82-6 ]
Downstream synthetic route of [ 22323-82-6 ]

[ 22323-82-6 ] Synthesis Path-Upstream 1~1

1
[ 22323-82-6 ]
[ 114746-70-2 ]

Reference： [1] ACS Catalysis, 2018, vol. 8, # 7, p. 6738 - 6744
[2] Tetrahedron, 2005, vol. 61, # 6, p. 1459 - 1480
[3] Tetrahedron, 2007, vol. 63, # 34, p. 8255 - 8266

[ 22323-82-6 ] Synthesis Path-Downstream 1~5

1
[ 22323-82-6 ]
[ 33332-28-4 ]
(S)-6-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)pyrazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28.2%	With sodium; at 130℃; for 16h;Sealed tube;	6-chloropyrazin-2-amine (0.980 g, 7.57 mmol), (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol (2 g, 15.13 mmol) and sodium (0.348 g, 15.13 mmol) were taken in a seal tube and heated at 130 C. for 16 hr and then the reaction mixture was quenched with methanol and ice cold water (100 mL) and extracted with ethyl acetate (5×50 mL). The combined organic layers were washed with water, saturated brine solution, dried over anhydrous sodium sulfate, filtered and concentrated to give the product (1 g, 4.26 mmol, 28.2% yield), LCMS (m/z) 265.1 [M+H]+.
28.2%	With sodium; at 130℃; for 16h;Sealed tube;	6-chloropyrazin-2-amine (0.980 g, 7.57 mmol),(S)-(2,2-dimethyl-l,3-dioxolan-4- yl)methanol (2 g, 15.13 mmol) and sodium (0.348 g, 15.13 mmol) were taken in a seal tube and heated at 130 C for 16 hr and then the reaction mixture was quenched with methanol and ice cold water (100 mL) and extracted with ethyl acetate (5 x 50 mL). The combined organic layers were washed with water, saturated brine solution, dried over anhydrous sodium sulfate, filtered and concentrated to give the product (1 g, 4.26 mmol, 28.2 % yield), LCMS (m/z) 265.1 [M+H]+.

Reference： [1]Patent: US2015/152108,2015,A1 .Location in patent: Paragraph 0421; 0422
[2]Patent: WO2016/79709,2016,A1 .Location in patent: Page/Page column 163-164

2
[ 497-09-6 ]
[ 67-64-1 ]
[ 22323-82-6 ]

Yield	Reaction Conditions	Operation in experiment
2.56 g		To a stirred solution of diacetonoid (11) (6 g) in DCM (60 mL),sat. NaHCO3 solution (2 mL) and NaIO4 (3.3 g) was added portionwise in 2e3 min. The reaction mixture was stirred for 2 h at RT.After 2 h, anhydrous sodium sulphate (2 g) was added and thereaction mixture was stirred for 1 h at RT. After completion of reaction time, the reaction mixture was filtered through vacuum filterand filtrate was concentrated on rotary evaporator at 28 C withcool water circulation. The crude (S)-()-glyceraldehyde was dissolved in ethyl acetate (40 mL) and ethanol (5 mL) followed bygradual addition of NaBH4 (0.65 g) at 0 C. This reaction mixturewas stirred at RT for 3 h. At that stage, acetone was added (5 mL) at0 C and allowed to stir at RT for 15 min. Then the reaction mixturewas cooled to 0 C and saturated NH4Cl solution was added dropwise with the dropper until there was no more evolution ofhydrogen gas. After this quenching process, the reaction mixturewas transferred to a separating funnel. The two layers were separated, from this the organic layer was separated and the aqueouslayer was extracted with diethyl ether twice. The combined organiclayers were washed with brine solution and dried over anhydrousNa2SO4 and concentrated under vaccum at 45 C to obtain a crudeproduct. The crude product was purified by silica gel columnchromatography using a solvent mixture of hexane: EtOAc (4: 1, v/v) to obtain a title compound (2.56 g, 85percent) with oil like characteristics. 1H NMR (300 MHz, CDCl3) d 4.19e4.27 (m, 1H), 4.04 (t,J 8.1 Hz, 1H), 3.78 (t, J 8.1 Hz, 1H), 3.69 (d, J 11.3 Hz, 1H), 3.59(dd, J 4.9, 11.1 Hz, 1H), 2.9(Bs, OH), 1.43 (s, 3H), 1.37 (s, 3H); 13CNMR (125 MHz, CDCl3) d 109.2, 76.1, 65.6, 62.8, 26.5, 25.1; IR (CHCl3)3420, 2987, 2936, 2884, 1457, 1372, 1214, 1157, 1051, 845 cm1;Specific rotation: [a ]D 20 ()10.28, (C 5, MeOH).

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 109,p. 134 - 145

3
[ 19745-07-4 ]
[ 22323-82-6 ]
(S)-2-chloro-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		To a stirred solution of cesium carbonate (492 g, 1510 mmol) in DMF (1000 mL) was added (S)-(2, 2-dimethyl-l, 3-dioxolan-4-yl) methanol (133 g, 1007 mmol) at 0 C. The resulting reaction mixture was stirred at room temperature for 30 min. Then a solution of 2, 5-dichloropyrazine (150 g, 1007 mmol) in DMF (500 mL) was added at 0 C and the resulted reaction mixture was stirred at 100 C for 4 h. (TLC System: 20% Ethyl acetate in Petether, R 0.5, UV active). The reaction mixture was diluted with ice cold water (500 mL), extracted with EtOAc (3 x 300 mL). The combined organic layer was washed with water (2 x 200 mL) and brine solution (100 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to obtain crude compound. The crude compound was purified by flash column chromatography (silica gel: 100-200 mesh, eluent: 10 % EtOAc in Hexane) to afford the desired product (,S)-2-chloro-5-((2, 2-dimethyl-l, 3- dioxolan-4-yl) methoxy) pyrazine (200 g, 768 mmol, 76 % yield) as a yellow liquid. LCMS (m/z): 245.1 [M+H]+.
71%		To a suspension of (S)-(2,2-dimethyl-l,3-dioxolan-4-yl)methanol (8.87 g, 67.1 mmol), in Nu,Nu-Dimethylformamide (DMF) (50 mL) stirred under nitrogen at 0C was added cesium carbonate (32.8 g, 101 mmol), the resulting reaction mixture was stirred at 0 C for 1 hr. To this added <strong>[19745-07-4]2,5-dichloropyrazine</strong> (10 g, 67.1 mmol). The resulting reaction mixture was stirred at 100 C for 6 hr. Progress of the reaction was monitored by TLC. TLC indicated starting material was consumed to form new polar spot with 0.3 Rf. The reaction mass was cooled to rt, added water(lOOmL) and extracted with Ethyl acetate(lOOmL). The organic layer was washed with water(100mLX2). The organic layer was dried over Na2S04 and filtered and concentrated to get crude as light brown liquid. The crude product was added to a silica gel (60-120) column and was eluted with Hex/EtOAc. Collected fractions: 30%EtOAc in Hexane the product was eluted. Concentrated the product fractions to afford (S)-2-chloro-5-((2,2-dimethyl-l,3-dioxolan-4-yl)methoxy)pyrazine (12 g, 47.7 mmol, 71.0 % yield) as light brown liquid, LCMS (m/z): 244.90 [M+H]+.

Reference： [1]Patent: WO2016/79709,2016,A1 .Location in patent: Page/Page column 273-274
[2]Patent: WO2016/79709,2016,A1 .Location in patent: Page/Page column 266-267

4
[ 22323-82-6 ]
[ 4983-28-2 ]
(S)-2-chloro-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃; for 4h;	To a stirred solution of <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (13 g, 100 mmol) in THF (100 mL) at 0 C was added (,S)-(2,2-dimethyl-l,3-dioxolan-4-yl)methanol (13.16 g, 100 mmol), triphenylphosphine (32.7 g, 124 mmol) followed by DEAD (19.71 mL, 124 mmol) and reaction was stirred at RT for 4 h. (TLC eluting system: 30% EtOAc in pet ether; R/-0.5; UV active). The reaction mixture was quenched with water (50 mL) and extracted into EtOAc (2x75 mL). Organic layer was separated and dried over anhydrous Na2S04, filtered and filtrate was evaporated to give crude product. The crude was purified by chromatography (Silicagel, eluent: 20% EtOAc in hexane) to afford (,S)-2-chloro-5-((2,2- dimethyl-l,3-dioxolan-4-yl)methoxy)pyrimidine (20g, 79 mmol, 79 % yield) as an off white solid. LCMS (m/z): 245.10; [M+H]+.

Reference： [1]Patent: WO2016/79709,2016,A1 .Location in patent: Page/Page column 276

5
[ 327056-62-2 ]
[ 22323-82-6 ]
C₁₂H₁₄N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 60℃; for 4h;	To a solution of <strong>[327056-62-2]5-fluoropicolinonitrile</strong> (366mg, 3 mmol) and (S)-(2,2-dimethyl- 1 ,3-dioxolan-4-yl)methanol (528 mg, 4 mmol) in THF (15 mL) was added NaH (60% in mineral oil, 160 mg, 4 mmol) at 0 C. The reaction was heated to 60 C and stirred for 4 h. The reaction mixture was diluted with water (50ml_) and filtered to afford Compound 2 (700 mg) without purification.

Reference： [1]Patent: WO2020/76951,2020,A1 .Location in patent: Page/Page column 34

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Technical Information

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

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[ CAS No. 22323-82-6 ] {[proInfo.proName]}

Quality Control of [ 22323-82-6 ]

Related Doc. of [ 22323-82-6 ]

Product Details of [ 22323-82-6 ]

Calculated chemistry of [ 22323-82-6 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 22323-82-6 ]

Application In Synthesis of [ 22323-82-6 ]

[ 22323-82-6 ] Synthesis Path-Upstream 1~1

[ 22323-82-6 ] Synthesis Path-Downstream 1~5

Technical Information

Related Functional Groups of [ 22323-82-6 ]

Alcohols

Related Parent Nucleus of [ 22323-82-6 ]

Dioxolanes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 22323-82-6 ]

Related Parent Nucleus of
[ 22323-82-6 ]