Name: 77-95-2|(1α,3R,4α,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid|95%
Brand: Ambeed
SKU: A121034
Price: 5.0 USD
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1
[ 77-95-2 ]
[ 665-27-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; toluene; for 12h;Reflux;	A solution of quinic acid 1 (10 g, 52 mmol) and p-toluenesulfonic acid monohydrate (0.99 g, 5.2 mmol) in DMF (25 mL) and toluene (90 mL) were heated under reflux with azeotropic removal of water (Dean-Stark apparatus). After 12 h the solution was cooled to room temperature. The solvent was removed under reduced pressure to give a solid, which was then heated under reflux in EtOAc (100 mL) for 4 h and the solution was cooled to room temperature. The solvent was then removed under reduced pressure to give quinide 7 as a colorless solid (9 g, 99%); m.p. 182-183 C; δH (300 MHz, DMSO-d6) 5.98 (1H, s), 5.32 (1H, d, J = 4.4 Hz), 4.91 (1H, d, J = 7.0 Hz), 4.68 (1H, apparent d, J = 5.4, Hz), 3.88 (1H, ddd, J = 4.7, 4.7, 4.5 Hz), 3.61-3.50 (1H, m), 2.33 (1H, apparent d, J = 11.2 Hz), 2.21-2.14 (1H, m), 1.95-1.98 (1H, m), 1.76 (1H, apparent t, J = 11.6 Hz); m/z (ES+) 174 [(M+H)+, 100%].
78%	With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; benzene; for 26h;Heating / reflux;	l,3,4-Trihydroxy-6-oxa-bicyclo[3.2.1]octan-7-one (2). In a 200 mL round- bottom flask fitted with a stirring bar, reflux condenser, Dean-Stark trap, and argon inlet, 5 g of quinic acid (1, 26 mmol) was placed and 10 mL of dry DMF was added via syringe and the slurry stirred at room temperature. Next, benzene 60 mL and p-toluenesulfonic acid 0.5 g were added, and the slurry was heated to reflux for 26 h. TLC was used confirm the completion of reaction. A 1:1 mixture of EtOAc and 12eptanes (100 mL) was added to the cooled reaction mixture. The mixture was stirred for 1 h at room temperature and filtered. The collected solid was again stirred with a 1:1 mixture of EtOAc and 12eptanes (100 mL) for 1 hr at room temperature and filtered. Tituration was repeated one more time with a 1:1 mixture of EtOAc and 12eptanes (100 mL) and the precipitate collected to give 3.5 g of Lactone 2 (78% yield). Mp: 192-193 0C, Rf 0.25 (EtOAc); MS: [M-H]": 171; 1H NMR (300 MHz, DMSO) δ 1.72 (t, J = 1.6 Hz, IH), 1.82-1.88 (m, IH), 2.07-2.13 (m, IH), 2.25 (d, J = 1.1 Hz, <n="14"/>IH), 3.49 (ddd, J = 11.4, 6.3, 5.7 Hz, IH), 3.82 (t, J = 4.5 Hz, IH), 4.61 (t, J = 5.1 Hz, IH), 4.816 (d, J = 6.0 Hz, IH), 5.23 (d, J = 4.5 Hz, IH), 5.89 (s, IH).
47%	at 230℃; for 0.25h;	Preparation of (-)-Quinide 6: <strong>[77-95-2](-)-Quinic acid</strong> 1, 20 g, was heated at 230 C. for 15 min. in an open flask. After cooling the glassy residue was recrystallized from methanol/acetone (v/v=9:1) to afford 8.5 g (47%) of (-)-quinide 6 δH (400 MHz; CD3OD) 4.76 (1H, t, J 5.6, 3-H), 4.03 (1H, t, J 4.4, 4-H), 3.76 (1H, ddd, J 4.4, 6 and 11.2, 5-H), 2.51 (1H, d, J 11.6, 6ax-H), 2.28 (1H, ddd, J 2.4, 5.6 and 11.6, 6eq-H), 2.08 (1H, ddd, J2.8, 6.4 and 11.6, 2eq-H) and 1.93 (1H, t, J 11.6, 2ax-H); δC (100 MHz; CD3OD) 179.6, 77.9, 73.2, 67.4, 66.8, 40.1 and 37.9.

26.8%	With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; toluene;Dean-Stark; Reflux;	1,5-quinide. Quinic acid (25 g, 130.1 mmol) and p-toluenesulfonic acid (500 mg, 2.622 mmol) were dissolved in anhydrous toluene (350 mL) and dimethylformamide (50 mL) in an oven-dried round bottom flask. The flask was equipped with a Dean-Stark apparatus and the vessel was refluxed overnight while stirring. The mixture was cooled to room temperature and toluene was evaporated. The remaining solution was cooled in an ice bath and solid was precipitated by the addition of a hexanes and ethyl acetate mixture (4:1). The precipitate was filtered and rinsed with diethyl ether to give a white solid (6.078 g, 26.8% yield). 1H NMR (600 MHz, Methanol-d4) δ 4.70 (dd, J=6.0, 4.9 Hz, 1H), 3.98 (t, J=4.6 Hz, 1H), 3.70 (ddd, J=11.2, 6.6, 4.4 Hz, 1H), 2.47 (d, J=11.4 Hz, 1H), 2.22 (ddd, J=11.4, 6.0, 3.0 Hz, 1H), 2.03 (dddd, J=11.8, 6.6, 2.9, 0.8 Hz, 1H), 1.87 (t, J=11.6 Hz, 1H).
26.8%	With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; toluene;Reflux;	Quinic acid (25 g, 130.1 mmol) and p-toluenesulfonic acid (500 mg, 2.622 mmol) were dissolved in anhydrous toluene (350 mL) and dimethylformamide (50 mL) in an oven-dried round bottom flask. The flask was equipped with a Dean-Stark apparatus and the vessel was refluxed overnight while stirring. The mixture was cooled to room temperature and toluene was evaporated. The remaining solution was cooled in an ice bath and solid was precipitated by the addition of a hexanes and ethyl acetate mixture (4:1). The precipitate was filtered and rinsed with diethyl ether to give a white solid (6.078 g, 26.8% yield). 1 H NMR (600 MHz, Methanol-74) d 4.70 (dd, 7 = 6.0, 4.9 Hz, 1H), 3.98 (t, 7 = 4.6 Hz, 1H), 3.70 (ddd, 7 = 11.2, 6.6, 4.4 Hz, 1H), 2.47 (d, 7 = 11.4 Hz, 1H), 2.22 (ddd, 7 = 11.4, 6.0, 3.0 Hz, 1H), 2.03 (dddd, 7 = 11.8, 6.6, 2.9, 0.8 Hz, 1H), 1.87 (t, 7 = 11.6 Hz, 1H)
	With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; toluene; for 18h;Inert atmosphere; Dean-Stark; Reflux;	A solution of d-(-)-quinic acid (1.96g, 10.2mmol) and p-toluenesulfonic acid (100mg, 0.52mmol) in anhydrous toluene (20mL) and anhydrous DMF (7mL) was refluxed under a Dean-Stark trap for 18h. The reaction mixture was cooled and concentrated under reduced pressure. The residue was diluted with CH2Cl2 (20mL) and hexane (10mL). The precipitated product was collected by vacuum filtration to afford the crude lactone 11 (1.77g) which was used in the next reaction step without further purification.
	With toluene-4-sulfonic acid; In hexane; N,N-dimethyl-formamide; at 90℃; for 18h;	Using compound 1 as starting material, compound 1 was added to a mixture of DMF and n-hexane. The catalyst p-toluenesulfonic acid. The reaction was carried out at 90 C for 18 hours. The reaction is as shown in Formula 13. While the synthesis from compound 2 to compound 3 was carried out in the same manner as described in PCT application WO2010 / 120698A1. The yield in two steps was 48%.
	Reflux;	Quinic acid (3 g, 15.61 mmol) was heated in an open flask at 220C for 90 min. The brown sticky residue was refluxed with EtOAc (60 mL) for 4 h and then the solution was cooled to room temperature. The solvent was removed under pressure to give 1,5-c-quinide as a colorless solid in 85% yield. NMR data were in accordance with the literature.28,29
	With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; benzene;	the starting bicyclic lactone 1 was obtained from commercial (-)-quinic acid as described previously by Hanessian et al., J. Org. Chem. 62, 465 (1997).
	toluene-4-sulfonic acid; In N,N-dimethyl-formamide; benzene;	Referring first to SCHEME I the starting bicyclic lactone 1 was obtained from commercial (-)-quinic acid as described previously [Hanessian et al., J. Org. Chem. 62, 465 (1997)].

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2
[ 67-56-1 ]
[ 77-95-2 ]
[ 191916-39-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With acetyl chloride; at 0 - 20℃; for 16h;	AcCI (2.044 g, 1 .850 ml_, 26.02 mmol) was added to a stirring solution of MeOH (37 ml.) in a flame dried, round bottom flask charged with argon at 0 0C. <strong>[77-95-2](-)-Quinic acid</strong> (7, 10.00 g, 52.04 mmol) was added to the mixture, and the suspension stirred for 16 h while warming to room temperature. The solid reactant dissolved as the reaction proceeded to afford a pale yellow solution. The reaction mixture was concentrated in vacuo, the residue redissolved in CHCI3, and then concentrated again (this process was repeated three times to remove the excess MeOH via azeotropic distillation). The product was isolated as a viscous yellow oil in quantitative yield (10.80 g, 52.38 mmol). Rf = 0.10 (30% EtOAc in hexanes); 1H NMR (300 MHz, CD3CN) δ 4.04-3.97 (1 H, m), 3.96-3.84 (1 H, m), 3.65 (3H, s), 3.34-3.26 (1 H, m), 2.09-1 .88 (3H, m), 1.74-1.63 (1 H, m), 4 exchangeable protons unobserved; 13C NMR (75 MHz, CD3CN) δ 175.0, 76.7 (2C), 71.3, 67.6, 53.0, 42.1 , 38.0.
92%	With toluene-4-sulfonic acid; at 20℃; for 24h;	[0179] For example, compound a is esterified and the hydroxyl groups are protected to result in compound b (p-TsOH, MeOH, rt, 24 h, 92%; TBDMSCl, TEA, DMF, rt, 18 h, 70%). The thioimidazolide, c, is prepared through reaction of b with 1,1 '-thiocarbonyl-diimidazole in methylene chloride (60 h, rt, 90%). Radical deoxygenation of c with tributyltin hydride in the presence of azobisisobutyronitrile (AIBN) produces the desoxy-ester, d (Bu3SnH, AIBN, toluene, 80 C, 2 h, 90%). Ester d is reduced to the alcohol, e (DIBAL-H, toluene, -78 C, 2 h, 60%), which then undergoes oxidation to form cyclohexanone derivative f (saturated NaI04 in water, MeOH, 0 C, 30 min, 78%), Reaction of f with ethyl (trimethylsilyl)acetate in the presence of lithium diisopropylamide (LDA) in THF (-78 C, 2 h, 86%) produces the cyclohexyldiene ester, g. The latter is reduced to the allylic alcohol, h (DIBAL-H, toluene, -78 C, 1 h, 78-95%), which is converted to chloride i by reaction with the complex made from N-chlorosuccinimide and dimethyl sulfide (-25 C, then 0 C, 80%). This chloride is treated with lithium diphenylphosphideO C (-78 C, 30 min), followed by oxidation with hydrogen peroxide, to form compound j. Compound j is partially deprotected to form compound k, which is dehydroxylated as described for compound c, to result in compound m. Compound m can react with a ketone precursor by methods described herein to form the 19-nor prodrugs of the invention.
91.3%	With thionyl chloride; at -15 - 20℃; for 12.75h;	Weigh quinic acid (1.92g, 10mmol) in dry 100mL round-bottomed flask,Dissolve in an appropriate amount of dry methanol, and place the flask in a constant temperature stirring reaction bath.The mixture was kept at -15 C for 15 min, and then thionyl chloride (0.98 mL, 13.5 mmol) was slowly added dropwise to the reaction system. After reacting for 30 min,The reaction solution was moved to room temperature and the reaction was continued for 12 h.After the reaction was completed, 3 mL of water was slowly added under ice-cooling, and extracted with ethyl acetate EtOAc (4×100 mL).The organic phases were combined and washed with saturated brine (100 mL×2).The organic phase was dried over anhydrous Na 2SO 4, filtered and evaporated.The TLC developer condition is CHCl3:CH3OH=3:1 (V:V),It was separated by silica gel column chromatography (CHCl3:CH3OH=3:1, V:V), and the Rf value was collected.1.88 g of a pale yellow oily liquid was obtained in a yield of 91.3%.

	With (1S)-10-camphorsulfonic acid;Reflux; Inert atmosphere;	To a suspension of quinic acid (1 g, 5.20 mmol) in MeOH (30 mL), (-)-10-camphorsulfonic acid (15 mg, 0.065 mmol) was added and the mixture was refluxed for 15 h under an Ar atmosphere.The methyl quinate 9 thus obtained was added with 2,2,3,3-tetramethoxybutane (1.01 g, 5.7 mmol), trimethylorthoformate (2.6 mL, 0.024 mmol) and (-)-10-camphorsulfonic acid (12 mg, 0.052 mmol) and the mixture was refluxed again. After 15 h the mixture was cooled and NaHCO3 (0.1 g) was added. Solution was concentrated under reduced pressure and the orange suspension was partitioned between EtOAc (30 mL) and saturated aqueous NaHCO3 (30 mL). The aqueous layer was extracted withEtOAc (30 mL) and the organic layer was dried over Na2SO4, filtered and the solvent was removed under reduced pressure. Recrystallization of the brownish residue from EtOAc and hexane(1:5, v/v) afforded 10 in 27% yield as an orange oil. NMR data werein accordance with the literature.19,29
6.54 g	With hydrogenchloride; at 40℃; for 9.5h;	Quinic acid (manufactured by Tokyo Chemical Industry Co., Ltd.; 5 g; 26 mmol) (Compound (5)) was dissolved in methanol (manufactured by Kokusan Chemical Co., Ltd.; 40 mL), and 10% hydrochloric acid solution in methanol (manufactured by Tokyo Chemical Industry Co., Ltd.; 10 mL) was added to the resulting solution, followed by stirring the resulting mixture at 40 C. for 9.5 hours. After concentrating the mixture with a rotary evaporator (manufactured by Tokyo Rikakikai Co., Ltd.), toluene (manufactured by Wako Pure Chemical Industries, Ltd.; 100 mL) was added to the mixture, and the resulting mixture was concentrated with a rotary evaporator, followed by drying under reduced pressure. The resulting crudely purified product of Compound (6) was used as it is for the subsequent reaction (yield, 6.54 g).

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[21]Patent: US2018/265445,2018,A1 .Location in patent: Paragraph 0044

3
[ 77-95-2 ]
[ 108-94-1 ]
[ 35949-53-2 ]

Yield	Reaction Conditions	Operation in experiment
50%		To a solution of 5 (10.91 g, 56.8 mmol) in toluene (40 mL) and DMF (40 mL) was added cyclohexanone (36.0 mL, 237.0 mmol). The reaction mixture was coupled to the dean-stark and refluxed for 50 hours. Then was added amberlite IR 120 (14.0 g) and refluxed for another 18 hours. The solution was filtered and neutralized with solution of sodium bicarbonate (5% m/v). The mixture was extracted with ethyl ether (3 x 200 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc / hexane) leading to compound 33 in 50% yield (7.2 g, 28.4 mmol).
	toluene-4-sulfonic acid; for 15h;Reflux;	Example 1: Synthesis of Compound (5) Quinic acid of compound (4) (100g), toluene (2L), cyclohexanone (167ml), TsOH (1g) are reacted under refluxing for 15h, and cooled to a room temperature to get a mixture. Then the above mixture is filtered and dried to obtain compound (5) 132g with a white solid powder. 1H-NMR (d-DMSO):1.348∼1.702(m,10H), 1.848(dd,J=3.2,17.6,1H), 2.173(m,2H), 2.326(d,J=9,1H), 3.28(s,1H), 4.234(d,J=6.4,1H), 4.433(m,1H), 4.475(q,1H), 6.013(s,1H); [M+1]+:255.
	With sulfuric acid; at 160℃;	Example 3; Alternate Preparation of ER-806730: [00128] Quinic acid (lwt), cyclohexanone (2.11 eq, 1.08 wt), and conc. sulfuric acid (0.011 eq, 0.0056 wt) were added to a reactor. The reaction mixture was heated to 160C and water was removed by azeotropic distillation (azeotrope begins at 100 C). The reaction was cooled to 90 C to 100 C and sodium bicarbonate (0.0096 wt) and toluene (3.6 wt) were added. The reaction was cooled to ambient temperature over 4-6 hours and the resulting precipitate was filtered, washed with toluene (2 x 0.9 wt), and dried to provide 1 (0.97 wt) as a white powder.

With toluene-4-sulfonic acid; In benzene; for 14h;Dean-Stark; Reflux;

The cinchona acid (60g), cyclohexanone (160 ml) with toluene sulfonic acid (600 mg) in benzene (450 ml) of the suspension device Dean-Stark in reflux for 14 hours. The reaction mixture after cooling to room temperature, poured into a saturated NaHCO 3 solution (150 ml). For water CH 2 Cl 2 extracting 3 times. Combined with the organic layer, water (2 times), salt water (1 time) washing, Na 2 SO 4 concentrated after drying, to obtain white solid, from recrystallization in ether (75g, 95%).

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4
[ 77-95-2 ]
[ 108-24-7 ]
[ 32469-24-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With pyridine; dmap; at 5℃; for 12h;	Quinic acid (compound 1, 961 mg, 5 mmol) was dissolved in 12 mL of aceticanhydride - pyridine 1:2 mixture. The solution was mixed with 4-dimethylaminopyridine (20 mg, 0.16 mmol) and stirred for 12 h at 5 C. The reaction mixture was then added to ice water, acidified to pH 3 and extracted with dichloromethane (DCM). The extract was dried with sodium sulphate and concentrated to give a white solid (1.75 g, 97% Yield).ESI: (M+H): 361.

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5
[ 77-95-2 ]
[ 100-52-7 ]
[ 216662-57-6 ]

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6
[ 77-95-2 ]
[ 67-64-1 ]
[ 32384-42-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With toluene-4-sulfonic acid; at 56℃; for 48h;Molecular sieve;	D-<strong>[77-95-2](-)-Quinic acid</strong> (3.0 g, 15.6 mmol) and p-toluenesulfonic acid (152 mg, 0.8 mmol) were suspended in distilled acetone (150 ml). The mixture was heated under reflux (56 C) for 48 h in a Soxhlet apparatus, which was equipped with an extraction thimble filled with molecular sieves (4 Å, Merck), activated overnight in an oven at 120 C. The reaction mixture was cooled to 0 C using an ice-bath; NaHCO3 (364 mg, 10.3 mmol) was added and the suspension was stirred for 1 h. The mixture was filtered and the organic phase was evaporated under vacuum to obtain the product as a white solid (yield 93%). M.p. 133-136 C; [α]D25 = -30.3 (c = 1, CH3OH); 1H NMR (500 MHz, CD3OD): δ 1.32 (CCH3, s, 3H), 1.49 (CCH3, s, 3H), 2.02 (C2-Heq, dd, 1H, Jgem = 14.6 Hz JC2Heq-C3H = 3.0 Hz), 2.26 (C6-Heq, dddd, 1H, Jgem = 11.7 Hz JC6Heq-C5H = 6.1 Hz JC6Heq-C2Hax = 2.3 Hz JC6Heq-C4H = 1.4 Hz), 2.36 (C2-Hax, ddd, 1H, Jgem = 14.6 Hz JC2Hax-C3H=7.7 Hz JC2Hax-C6Heq = 2.3 Hz), 2.53 (C6-Hax, d, 1H, Jgem = 11.7 Hz), 4.30 (C4-H, ddd, 1H, JC4H-C3H = 6.5 Hz JC4H-C5H = 2.5 Hz JC4H-C6Heq = 1.4 Hz), 4.52 (C3-H, ddd, 1H, JC3H-C2Hax) = 7.7 Hz JC3H-C4H = 6.5 Hz JC3H-C2Heq = 3.0 Hz), 4.67 (C5-H, dd, 1H, JC5H-C6Heq = 6.1 Hz JC5H-C4H = 2.5 Hz); 13C NMR (125.4 MHz, CD3OD): δ 24.54 (q, CH3), 27.32 (q, CH3), 35.55 (t, C6), 38.98 (t, C2), 72.28 (d, C3), 72.90 (d, C4), 73.62 (s, C1), 76.62 (d, C5), 110.74 (s, C8), 180.03 (s, C7); IR (cm-1): 3583, 2932, 1777, 1315, 1161, 1075, 980; MS (ESI+): 215 m/z (50, [M-H]+), 237 m/z (100, [M-Na]+).
93%	With toluene-4-sulfonic acid; at 56℃; for 48h;	D-<strong>[77-95-2](-)-Quinic acid</strong> (3.0 g, 15.6 mmol) and p-toluenesulfonic acid (152 mg, 0.8 mmol) were suspended in distilled acetone (150 ml). The mixture was heated under reflux (56 C) for 48 h in a Soxhlet apparatus, which was equipped with an extraction thimble filled with molecular sieves (4 Å, Merck), activated overnight in an oven at 120 C. The reaction mixture was cooled to 0 C using an ice-bath; NaHCO3 (364 mg, 10.3 mmol) was added and the suspension was stirred for 1 h. The mixture was filtered and the organic phase was evaporated under vacuum to obtain the product as a white solid (yield 93%). M.p. 133-136 C; [α]D25 = -30.3 (c = 1, CH3OH); 1H NMR (500 MHz, CD3OD): δ 1.32 (CCH3, s, 3H), 1.49 (CCH3, s, 3H), 2.02 (C2-Heq, dd, 1H, Jgem = 14.6 Hz JC2Heq-C3H = 3.0 Hz), 2.26 (C6-Heq, dddd, 1H, Jgem = 11.7 Hz JC6Heq-C5H = 6.1 Hz JC6Heq-C2Hax = 2.3 Hz JC6Heq-C4H = 1.4 Hz), 2.36 (C2-Hax, ddd, 1H, Jgem = 14.6 Hz JC2Hax-C3H=7.7 Hz JC2Hax-C6Heq = 2.3 Hz), 2.53 (C6-Hax, d, 1H, Jgem = 11.7 Hz), 4.30 (C4-H, ddd, 1H, JC4H-C3H = 6.5 Hz JC4H-C5H = 2.5 Hz JC4H-C6Heq = 1.4 Hz), 4.52 (C3-H, ddd, 1H, JC3H-C2Hax) = 7.7 Hz JC3H-C4H = 6.5 Hz JC3H-C2Heq = 3.0 Hz), 4.67 (C5-H, dd, 1H, JC5H-C6Heq = 6.1 Hz JC5H-C4H = 2.5 Hz); 13C NMR (125.4 MHz, CD3OD): δ 24.54 (q, CH3), 27.32 (q, CH3), 35.55 (t, C6), 38.98 (t, C2), 72.28 (d, C3), 72.90 (d, C4), 73.62 (s, C1), 76.62 (d, C5), 110.74 (s, C8), 180.03 (s, C7); IR (cm-1): 3583, 2932, 1777, 1315, 1161, 1075, 980; MS (ESI+): 215 m/z (50, [M-H]+), 237 m/z (100, [M-Na]+).
70.6%	With toluene-4-sulfonic acid; for 24h;Reflux; Molecular sieve;	D-<strong>[77-95-2](-)-Quinic acid</strong> (30.0 g, 0.156 mol,According to the literature Valentina Sinisi.Et al.,“Interaction of chlorogenic acids and quinides from coffee with human serumAlbumin”,Food Chemistry,Preparation of 2015(168):332-340 method)P-toluenesulfonic acid monohydrate (1.50 g, 7.8 mmol),Acetone (1200.0 ml) was put into a single-mouth bottle.A Soxhlet extractor with a molecular sieve insideHeat reflux reaction for 24h.When the system starts to react, it is a solid-liquid mixed phase.As the reaction continues,It dissolved in about 8 hours.The molecular sieve was changed every 8 hours to ensure that the generated water was removed as much as possible.After the reaction is completed,Cool the system to 0C,Add NaHCO3 (8.7g, 0.66eq) and stir for 1h.filter,Spin dryLight yellow solid.Recrystallization from ethyl acetate/petroleum ether23.6 g of 3,4-oxy-isopropylidquinuconic acid-1,5-lactone (compound 1a) is obtained as an off-white solid.Yield: 70.6%

104 g	With sulfuric acid; sodium sulfate; for 5h;Reflux;	5 mL of sulfuric acid was added dropwise under stirring to a mixture of 100 g of quinic acid, 500 g of anhydrous sodium sulfate, and 2500 mL of acetone, and the mixture was heated to reflux for 5 hours. After the mixture was left to cool naturally, 200 mL of a 5% aqueous solution of sodium hydrogen carbonate was added dropwise thereto to neutralize sulfuric acid, and the solvent was distilled off under reduced pressure. 1500 mL of ethyl acetate was added to the residue, and the mixture was washed with a 5% aqueous solution of sodium hydrogen carbonate and then with a saline solution. Subsequently, the mixture was dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. Thus, 104 g of 3,4-O-isopropylidene-1,5-quinide lactone was obtained.
104 g	With sulfuric acid; sodium sulfate; for 5h;Reflux;	Sulfuric acid (5 mL) was added dropwise to a mixture of quinic acid (100 g), anhydrous sodium sulfate (500 g) and acetone (2500 mL) with stirring and heated under reflux for 5 hours. After standing to cool, 5% aqueous sodium hydrogen carbonate solution (200 mL) was added dropwise to neutralize the sulfuric acid, and the solvent was distilled off under reduced pressure. Ethyl acetate (1500 mL) was added to the residue, the mixture was washed with 5% aqueous sodium hydrogencarbonate solution and then with brine, dried over anhydrous magnesium sulfate,Ethyl acetate was distilled off under reduced pressure to obtain 3,4-O-isopropylidene-1,5-quinidolactone (104 g).

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[3]Food Chemistry,2015,vol. 168,p. 332 - 340
[4]Food Chemistry,2015,vol. 168,p. 332 - 340
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[12]Patent: CN108003027,2018,A .Location in patent: Paragraph 0116; 0117; 0120; 0121
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7
herbacetin 7-O-(6''-quinylglucoside) [ No CAS ]
[ 77-95-2 ]
[ 527-95-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In water

Reference： [1]Nawwar, Mahmoud A. M.; El-Sissi, Hassan I.; Barakat, Heba H. [Phytochemistry, 1984, vol. 23, # 12, p. 2937 - 2940]

8
[ 77-95-2 ]
[ 77-76-9 ]
[ 32384-42-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With toluene-4-sulfonic acid; In acetone; for 1h;Reflux;	A suspension of <strong>[77-95-2]D-(-)-quinic acid</strong> (8) (1.52 g,7.89 mmol), 2,2-dimethoxypropane (3.50 mL, 28.6 mmol), and p-TsOH*H2O (151.7 mg, 0.80 mmol) in acetone (78 mL) was stirred for 1 h under reflux, and Et3N (0.3 mL, 2.2 mmol) was added to the mixture. The resulting mixture was concentrated and the residual oil was purified by chromatography on silica gel (hexane/EtOAc) to afford the corresponding lactone (1.64 g, 98%) as solids.
98%		i) Quinic acid 3 (3.0 g, 15.6 mmol) was weighed into round bottomed flask equipped with stirring bar. Acetonitrile (200 mL) was added, followed by addition of Amberlyst 15 (3.5 g), and the mixture was refluxed for 2 days. The mixture was cooled to room temperature and 2,2-dimethoxypropane (3.8 mL, 3.25 g, 31.2 mmol, 2 equiv.) was added and refluxed for 3 h. The reaction mixture was filtrated through Celite plug and the solvent was evaporated to give pure (3aR,4R,7S,8aR)-7-hydroxy-2,2-dimethyltetrahydro-4,7-methano[1,3]dioxolo[4,5-c]oxepin-6(4H)-one as a beige solid (3.28 g, 98%). 1H NMR (500 MHz, CDCl3): d 4.71 (dd, J 6.1, 2.5 Hz, 1H-1), 4.51-4.47 (m, 1H-3), 4.29 (ddd, J 6.7, 2.4, 1.5 Hz, 1H-2), 3.16 (s, 1HeOH), 2.63 (d, J 11.7 Hz, 1H-6), 2.36 (ddd, J 14.7, 7.6, 2.3 Hz, 1H-4), 2.33-2.27 (m, 1H-6), 2.17 (dd, J 14.6, 2.9 Hz, 1H-4), 1.51 (s, 3HeCH3), 1.31 (s, 3HeCH3); 13C NMR (125 MHz, CDCl3): d 179.08 (C]O), 109.90 (Cisop.), 75.97 (C1), 72.19 (C5), 71.66 (C2), 71.60 (C3), 38.23 (C4), 34.37 (C6), 27.08 (CH3), 24.41 (CH3); HRMS calculated for [M]+ 214.0841, found 214.0913. The spectral data of the compound is consistent with the literature data [10]. ii) Lactone ((3aR,4R,7S,8aR)-7-hydroxy-2,2-dimethyltetrahydro-4,7-methano[1,3]dioxolo[4,5-c]oxepin-6(4H)-one) synthesized in section 4.2 i) (3.28 g, 15.3 mmol) was dissolved in Et2O (100 mL) at 0 C. Et3N (4.3 mL, 3.1 g, 30.6 mmol, 2 equiv.) was added followed by slow addition of MsCl (1.8 mL, 2.6 g, 23 mmol, 1 equiv.). The ice bath was removed after 5 min and the mixture was left stirring for 2 h at room temperature forming a thick solution. The mixture was diluted with EtOAc (100 mL) and quenched with H2O (100 mL). Layers were separated and the aqueous phase was extracted with CH2Cl2 (3 - 50 mL). The organic phases were combined, dried with anhydrous MgSO4, filtered through silica pad (3 cm) and the solvents were evaporated to give pure 4 as a beige solid (4.24 g, 95%). 1H NMR (500 MHz, CDCl3): d 4.80 (dd, J 6.4, 2.5 Hz, 1H-1), 4.57-4.45 (m, 1H-3), 4.31 (ddd, J 6.2, 2.1, 0.9 Hz, 1H-2), 3.28 (s, 3H -OMs-CH3), 3.12-3.05 (m, 1H-6), 2.83 (d, J 11.8 Hz, 1H-4), 2.54 (ddd, J 14.4, 7.7, 2.4 Hz, 1H-6), 2.39 (dd, J 14.5, 3.0 Hz, 1H-4),1.52 (s, 3HeCH3), 1.32 (s, 3HeCH3). 13C NMR (125 MHz, CDCl3): d 172.91 (C]O), 110.41 (Cisop.), 82.27 (C5), 75.82 (C1), 72.01 (C2), 71.17 (C3), 41.34 (OMs-CH3), 36.60 (C4), 33.24 (C6), 27.06 (CH3), 24.45 (CH3); HRMS calculated for [M+Na]+ 315.0515, found 315.0479. The spectral data of the compound is consistent with the literature data [36].
81.2%	With toluene-4-sulfonic acid; In acetone; at 40℃; for 4h;Reflux;	<strong>[77-95-2]D-(-)-quinic acid</strong> (40.0 g, 0.208 mol,, p-toluenesulfonic acid monohydrate (0.8 g, 4.16 mmol),Acetone (200.0 ml) and 2,2-dimethoxypropane (75.8 g, 0.728 mol) were placed in the reaction port vial., heating and refluxing reaction for 4h. When the system starts to react, it is a solid-liquid mixed phase.As the reaction continues,All dissolved.The reaction is completed, 40 C,Concentrated and dried under reduced pressure,Ethyl acetate (300.0 ml) was added to the residue.Add 5% NaHCO3 aqueous solution (300.0 ml), stir, and separate.The aqueous phase was extracted with ethyl acetate (100.0 mL).Wash with a saturated aqueous solution of sodium chloride, dry over anhydrous sodium sulfate, filtered and dried.A pale yellow solid. Recrystallized from ethyl acetate/petroleum ether system,Obtained 36.2g of white solid3,4-oxo-isopropylidene quinic acid-1,5-lactone(Intermediate 1-1a), yield: 81.2%

80%	With toluene-4-sulfonic acid; In acetone; for 2h;Heating / reflux;	3,4-O-lsopropylidene-l,5-quinic Lactone (4) A mixture of quinic qcid (l)(20g, 104.1 mMol), p-totuenesulfonic acid monohydrate (0.2g), 2,2-dimethoxypropane ( 38g, 364 mMol), and acetone ( 100 mL) was heated to reflux for 2 hr. The reaction mixture was cooled down, and solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (100 mL), washed with 5% aqueous sodium bicarbonate (100 mL). The aqueous phase was back-extracted with ethyl acetate (5Ox 2 mL). The combined organic extracts were dried (Na2SO4), filtered, and the solvents were removed in vacuo. The residue was crystallized with hot ethyl acetate, got white solid 16g ( 80% yield), mp: 147-149 0C Rf = 0.3 (EtoAC: Hex = 3:7). MS: [M+Na]+ = 237. 1H NMR (CDCI3) δ 1.37 (s, 3H), 1.55 (s, 3H), 2.21 (dd, J= 14.7, 3.0 Hz, IH), 2.30-2.44 (m, 2H), 2.68 (d, J = 11.7 Hz, IH), 2.83(s, IH), 4.32-4.36 (m, IH), 4.51-4.58 (m, IH), 4.79 (dd, J = 2.6, 6.3 Hz, IH).
73%	With toluene-4-sulfonic acid; In acetone; at 20℃; for 96h;	The cinchona acid (103g), 2,2-dimethoxy propane (200 ml) with toluene sulfonic acid (850 mg) in acetone (700 ml) at room temperature in the stirring suspension of 4 days. Reduced pressure to remove the solvent and the excess reagent. Rapid column chromatography (hexane/EtOAc=2/1 - 1.5/1) purified obtain lactone 240 (84g, 73%)
72%	With toluene-4-sulfonic acid; In acetone;Reflux;	2,2-Dimethoxypropane (4.87 g, 46.83 mmol) was added to a suspension of quinic acid (3 g, 15.61 mmol) and p-toluenesulfonic acid (216 mg, 1.15 mmol) in acetone (60 mL) and the mixture was heated at reflux for 2 h. After cooling, neutralization with NaHCO3 (5%) was performed and the mixture was stirred for 1 h at room temperature. The reaction mixture was sequentially extracted with CH2Cl2 (three times, 20 mL at time) and washed with water (two times, 20 mL at time). The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. Lactone 5 was obtained as a white solid in 72% yield and was used in the next step without further purification. NMR data were in accordance with the literature.26
	With toluene-4-sulfonic acid; In ethyl acetate; for 3h;Inert atmosphere; Reflux;	At first, d-(-)-quinic acid 7 (1g, 5.2mmol) was suspended in EtOAc (30mL). p-Toluenesulfonic acid monohydrate (10mg, 0.052mmol) and 2,2-dimethoxypropane (1.96mL, 15.6mmol) were then added. The mixture was heated at reflux for 3h. After cooling, the solvent was removed under reduced pressure. The residual solid, lactone 8 was used in the next step without further purification. NMR data were in accordance with the literature data.14
	With toluene-4-sulfonic acid; In acetone; for 2h;Reflux; Large scale;	[0091] The compound of formula 100 (lactone) can be obtained in the following manner. Specifically, a solution of quinic acid (20 kg, 104 mol; [α]D-43.7 (c=1.12, water); “Merck Index 11th ed.”, 8071: [α]D-42 to -44 (water)), 2,2-dimethoxypropane and p-toluenesulfonic acid monohydrate in acetone is heated at reflux for two hours. The reaction is quenched by addition of sodium ethoxide in ethanol and most of the solvent is distilled in vacuo. The residue is partitioned between ethyl acetate and water. The aqueous layer is back-extracted with ethyl acetate and the combined organic layers are washed with aqueous sodium bicarbonate. Most of the ethyl acetate is distilled in vacuo to leave a pale yellow solid residue of the compound of formula 100.
	With toluene-4-sulfonic acid; In ethyl acetate; at 70℃; for 0.5h;	Put quinic acid and ethyl acetate into a round bottom flask, add p-toluenesulfonic acid and 2,2-dimethoxypropane, set the temperature at 70C and rotate at 200r/min, and stir for 0.5 h, after the stirring, concentrate under reduced pressure to remove ethyl acetate to obtain a brown solid 2;

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9
[ 191916-39-9 ]
[ 77-95-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With water; sodium hydroxide; In tetrahydrofuran; at 20℃; for 5h;	Compound 10 (0.220 g, 1.066 mmol) was dissolved in a mixed solvent of tetrahydrofuran (2 mL) and water (2 mL). Powdered sodium hydroxide (0.086 g, 2.150 mmol) was then added, and the mixture was stirred at room temperature for 5 h. An aqueous solution of HCl (2.000 M, 1.1 mL, 2.200 mmol) was then added. The mixture was passed through a column of acidic resin (10 cm) with a mixed solvent of methanol and water (1:1) as the eluent. Evaporation of the solvents under vacuum afforded (-)-quinic acid 1 (0.184 g, 0.958 mmol) as white crystals in 90% yield, mp 166-167 C (lit. 9g 167-168 C). [α]D25 = -43.2 (c 1.80, H2O) {lit. 9g [α]D30 = -43.6 (c 2.03, H2O)}. 1H NMR (400 MHz, CD3OD) δ 4.09 (dd, J1 = 6.5 Hz, J2 = 5.2 Hz, 1H, H-4), 3.95-4.05 (m, 1H, H-5), 3.35-3.42 (m, 1H, H-3), 2.00-2.15 (m, 3H, two H-6 and one H-2), 1.86 (dd, J1 = 13.4 Hz, J2 = 9.8 Hz, 1H, H-2). 13C NMR (100 MHz, CD3OD) δ 177.64 (COOH), 77.11 (C-1), 76.90 (C-4), 71.99 (C-5), 68.06 (C-3), 42.44 (C-6), 38.45 (C-2). HRMS (ESI) calcd for C8H14O6Na [M+Na]+: 229.0688; found: 229.0481. IR (KBr film): ν = 3408, 2965, 1726, 1646, 1440, 1267, 1085, 709 cm-1.

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[3]Journal of Agricultural and Food Chemistry,2016,vol. 64,p. 7298 - 7306

10
[ 77-95-2 ]
[ 431-03-8 ]
[ 149-73-5 ]
[ 176798-26-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With CSA; In methanol; at 85℃; for 45h;Reflux; Inert atmosphere;	To a solution of (-)-quinic acid (6) (1.0 g, 5.2 mmol), methyl orthoformate (2.8 mL, 26.0 mmol), and 2,3-butandione (0.9 mL, 10.4 mmol) in MeOH (15 mL) was added CSA (12 mg, 5.2 mmol) at room temperature and the resulting mixture was stirred for 45 h at 85 C. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (hexane/AcOEt=1:4) to give 3 as a white solid (1.495 g, 90%). Mp: 137-138 C; [α]D24 +136.0 (c 1.0, CHCl3); IR (KBr) 3442, 2952, 1727, 1451, 1279, 1243, 1133, 1042, 911 cm-1; 1H NMR (600 MHz, CDCl3) δ 1.29 (s, 3H), 1.33 (s, 3H), 1.91 (t, J=12.5 Hz, 1H), 2.03 (dd, J=15.0, 3.0 Hz, 1H), 2.09 (ddd, J=12.5, 4.8, 3.0 Hz, 1H), 2.18 (td, J=14.8, 3.0 Hz, 1H), 3.25 (s, 3H), 3.26 (s, 3H), 3.59 (dd, J=10.5, 3.0, Hz, 1H), 3.78 (s, 3H), 4.18 (q, J=3.0 Hz, 1H), 4.30 (ddd, J=12.5, 10.5 4.8 Hz, 1H); 13C NMR (150 MHz, CDCl3) δ 17.7, 17.8, 37.4, 38.7, 47.9, 52.9, 62.4, 69.2, 72.8, 75.8, 99.8, 100.4, 174.3; HRMS (FAB) calcd for C14H24O8Na [M+Na]+ 343.1369, found 343.1364.

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11
[ 77-95-2 ]
[ 77-76-9 ]
[ 130474-38-3 ]

Yield	Reaction Conditions	Operation in experiment
83.8%	Benzylsulfonic acid; In benzene; for 15h;Heating / reflux;	Preparation of DW-13a To a suspension of <strong>[77-95-2](-)-Quinic acid</strong> (46 g, 0.239 mol) in 2,2-dimethoxypropane (60 mL) and benzene (180 mL) was added TsOH (0.1 g) After refluxing for 15 hours, the reaction mixture was cooled to room temperature and quenched with triethylamine (0.5 mL). The solvent was removed under reduced pressure, and the residue was treated with ethyl acetate (100 mL). After filtration, the filtrate was concentrated and recrystallized in hexane-ethyl acetate to yield a lactone as white needles (43 g, 83.8%). mp 137-138 (C. [a]D25=-30.0((c 1.27, CHCl3) IR (KBr): 3421, 1776, 1073 cm-1. 1H NMR: d4.73 (dd, J=6.0, 2.4 Hz, 1H), 4.50 (ddd, J=7.5, 6.0, 2.7 Hz, 1H), 4.31 (ddd, J=6.3, 2.4, 1.2 Hz, 1H), 2.83 (s, 1H), 2.66 (d, J=12.0 Hz, 1H), 2.37 (ddd, J=14.7, 7.5, 2.4 Hz, 1H), 2.31 (dddd, J=12.0, 6.3, 2.4, 1.2 Hz, 1H), 2.19 (dd, J=14.7, 2.7 Hz, 1H), 1.53 (s, 3H), 1.33 (s, 3H). 13C NMR: d179.2, 109.9, 75.88, 72.21, 71.69, 71.62, 38.13, 34.42, 27.09, 24.44. Anal. Calcd for C10H14O5: C, 56.07; H, 6.59. Found: C, 56.13; H, 6.30.

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12
[ 77-95-2 ]
[ 176798-33-7 ]
[ 149-73-5 ]
[ 176798-26-8 ]

Yield	Reaction Conditions	Operation in experiment
76%		To a suspension of d-(-)-quinic acid (1g, 5.2mmol) in MeOH (30mL), (±)-10-camphorsulfonic acid (12mg, 0.052mmol) was added. Reaction mixture was then refluxed overnight. After cooling, 2,2,3,3-tetramethoxybutane 15 (927mg, 5.7mmol), trimethyl orthoformate (2.6mL, 0.024mol), and (±)-10-camphorsulfonic acid (12mg, 0.052mmol) were added and mixture again refluxed overnight. Powdered NaHCO3 (0.1g) was added to the cold reaction mixture. Solution was concentrated under reduced pressure and the residue partitioned between EtOAc (30mL) and saturated aqueous NaHCO3 (30mL). The aqueous layer was extracted once with EtOAc (30mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under vacuum. Crude product was recrystallized from EtOAc/n-hexane=1/5 to afford compound 16 (1.28g, 76% from quinic acid) as a white solid. NMR data are in accordance with the literature data.16

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 6839 - 6841
[2]Organic and Biomolecular Chemistry,2004,vol. 2,p. 1592 - 1596
[3]Tetrahedron Asymmetry,2013,vol. 24,p. 785 - 790

13
[ 77-95-2 ]
[ 95639-53-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With oxygen; potassium hydroxide; 9-(2-mesityl)-10-methylacridinium perchlorate; In water; acetonitrile; at 20℃; for 18h;Sealed tube; Irradiation;	General procedure: D-Glucono-1,5-lactone (4) (35.6 mg, 0.20 mmol), 9-mesityl-10-methylacridinium perchlorate (2) (8.2 mg, 0.02 mmol, 10 mol%) and LiOH (4.7 mg, 0.20 mmol, 1 equiv)was placed in a side-arm flask equipped with a stirrer bar. The flask was capped with arubber septum, and then, was evacuated and refilled with oxygen three times. Then,H2O (1.0 mL) and acetonitrile (1.0 mL) were added via syringe into the flask, whichwas irradiated with an LED lamp (470 nm). After 18 h at ambient temperature, thereaction mixture was opened to the air and the solvent was removed under reducedpressure. The residue was purified by flash-column chromatography (methanol/ethylacetate = 1:7) to give D-arabinose (5) (19.2 mg, 0.13 mmol, 64% yield).

Reference： [1]Chemistry Letters,2020,vol. 49,p. 1309 - 1311
[2]Journal of the American Chemical Society,2001,vol. 123,p. 10927 - 10934
[3]European Journal of Organic Chemistry,2016,vol. 2016,p. 3856 - 3861

14
[ 77-95-2 ]
ZnCl₂ [ No CAS ]
[ 350-29-8 ]

Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 4087 - 4090

15
[ 138-59-0 ]
[ 77-95-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: methanol; diethyl ether / -20 - -15 °C 2: 78 percent / Et₃N, 4-(dimethylamino)pyridine / dimethylformamide / 4 h / 0 °C 3: 87 percent / 3.0M t-BuOOH / VO(acac)2 / CH₂Cl₂; toluene / 18 h / Heating 4: 82 percent / Bu₄NF / tetrahydrofuran / 0.03 h 5: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 6: 72 percent / H₂ / Raney-Ni / ethyl acetate / 3420 Torr 7: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H₂O / 1) 1 h, 2) 15 h, r.t.
	Multi-step reaction with 8 steps 1: methanol; diethyl ether / -20 - -15 °C 2: 83 percent / TsOH / CH₂Cl₂ / 1.5 h / Ambient temperature 3: 88 percent / Et₃N, 4-(dimethylamino)pyridine / dimethylformamide / 6 h / Ambient temperature 4: 70 percent / HCl / methanol; H₂O / 0.25 h 5: 81 percent / 3.0M t-BuOOH / VO(acac)2 / CH₂Cl₂; toluene / 24 h / Ambient temperature 6: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature 7: 72 percent / H₂ / Raney-Ni / ethyl acetate / 3420 Torr 8: 90 percent / 1) KOH, 2) 80percent AcOH / tetrahydrofuran; H₂O / 1) 1 h, 2) 15 h, r.t.

Reference： [1]Meier; Tamm [Helvetica Chimica Acta, 1991, vol. 74, # 4, p. 807 - 818]
[2]Meier; Tamm [Helvetica Chimica Acta, 1991, vol. 74, # 4, p. 807 - 818]

16
[ 77-95-2 ]
[ 615-67-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1844,vol. 51,p. 146

17
[ 77-95-2 ]
[ 108-24-7 ]
[ 64-19-7 ]
[ 32469-24-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With perchloric acid; at 20 - 60℃;	Synthesis of the cationic glycomimicking amphiphile 1 (Scheme I).Step i (Scheme I). D (-) Quinic acid (Ig, 5.2 mmol) was suspended in a 2:1 (v/v) mixture of acetic acid-acetic anhydride (10 mL) and a drop of perchloric acid was added to it at room temperature. The reaction mixture became clear as the temperature increased to 50-60 0C after the addition of perchloric acid. The resulting solution was left stirred at room temperature for a further 12 h, diluted with ice-cold water and extracted with chloroform (3 x 100 mL). The organic layer was again washed with water (3 x 100 mL), dried over sodium sulphate, filtered and the solvent evaporated on a rotavapor. Crystallization of the residue from CHC13/Hexane (2:8) afforded 1.7 g (91% yield) of the pure title compound 1, 3, 4, 5- tetracetoxycyclohexane carboxylic acid (Intermediate I, Scheme I) as a white solid. 1H NMR (300 MHz, CDCl3): δ/ppm = 1.9-2.0 [dd, IH, 6-H]; 2.0-2.3 [4s, 12H, 4 x - COCH3]; 2.4-2.5 [m, 2H, 6-H 2-H]; 2.5-2.6 [dd, IH, 2-H']; 4.95-5.05 [dd, IH, 4-H]; 5.3- 5.45 [ddd, IH, 5-H]; 5.5-5.6 [m, IH, 3-H].
	With perchloric acid; at 50 - 60℃; for 12h;	Example 9 Step A Synthesis of 1,3,4,5-tetraacetoxycyclohexane carboxylic acid To a suspension of <strong>[77-95-2]D-(-)-quinic acid</strong> (2 g) in a 2 : 1 mixture of acetic acid-acetic anhydride (15 mL) one drop of perchloric acid was added at room temperature. As the reaction temperature increased to 50-60 C, the mixture became clear. The solution was stirred for a further 12 h, diluted with chloroform and then successively extracted with saturated aq.NaHCO3 and water. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was finally precipitated by addition of hexane to give 1,3,4,5-tetraacetoxycyclohexane carboxylic acid (3 g).

Reference： [1]Patent: WO2009/109996,2009,A2 .Location in patent: Page/Page column 15; 20
[2]Patent: EP2468741,2012,A1 .Location in patent: Page/Page column 11

18
[ 77-95-2 ]
[ 93413-62-8 ]
4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol D-quinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 20℃;Reflux;	Example 13[00154] A 100 ml one necked flask equipped with a magnetic stirrer was charged with ODV base (3 g, 11.39 mmol) and EtOH 95% (9ml), the suspension being stirred at reflux. D- Quinic acid (2.4g 12.49 mmol) was added and a clear solution was obtained. After stirring overnight at room temperature, the mixture was cooled to - 1O0C. Toluene (6 ml) was added and a clear solution appeared. The mixture was evaporated to dryness to get amorphous ODV Quinic. X-ray powder diffraction pattern is depicted in Figure 13

Reference： [1]Patent: WO2010/8735,2010,A2 .Location in patent: Page/Page column 18-19

19
[ 327-97-9 ]
[ 331-39-5 ]
[ 77-95-2 ]

Reference： [1]Chemistry of Natural Compounds,2010,vol. 46,p. 303 - 304
[2]Molecules,2018,vol. 23

20
[ 327-97-9 ]
[ 32719-11-2 ]
[ 1258222-08-0 ]
[ 1258222-09-1 ]
[ 331-39-5 ]
[ 77-95-2 ]
[ 905-99-7 ]
[ 14534-61-3 ]
[ 202650-88-2 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 12578 - 12584

21
[ 327-97-9 ]
[ 32719-11-2 ]
[ 1258222-08-0 ]
[ 1258222-09-1 ]
[ 331-39-5 ]
[ 77-95-2 ]
[ 905-99-7 ]
[ 202650-88-2 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 12578 - 12584

22
[ 327-97-9 ]
[ 1258222-08-0 ]
[ 1258222-09-1 ]
[ 331-39-5 ]
[ 77-95-2 ]
[ 905-99-7 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 12578 - 12584

23
[ 67-56-1 ]
[ 327-97-9 ]
[ 3843-74-1 ]
[ 77-95-2 ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2011,vol. 69,p. 161 - 167

24
[ 641571-10-0 ]
[ 77-95-2 ]
nilotinib quinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 2,2,2-trifluoroethanol; at 40℃; for 4h;	[00228] <strong>[641571-10-0]Nilotinib</strong> base (0.300 g, 0.57 mmol) was dissolved in TFE (2 mL) at 40C to obtain a mixture. The mixture was stirred and added to a solution of D-quinic acid (0.109g, 0.57 mmol) in TFE (1 mL) at 40C. The resulting clear solution was stirred for about 4 h at 40C and it was subsequently cooled to 5C. The mixture was kept at 5C overnight and then MTBE (1.5 v/v) was added to the mixture at room temperature leading to precipitation. The precipitate was filtered to give <strong>[641571-10-0]Nilotinib</strong> quinate form I.

Reference： [1]Patent: WO2011/163222,2011,A1 .Location in patent: Page/Page column 39

25
[ 77-95-2 ]
[ 204254-96-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / acetone / 2 h / Reflux; Large scale 2.1: ethanol / 2 h / 20 °C 2.2: 1 h / 0 - 10 °C 3.1: pyridine; sulfuryl dichloride / dichloromethane / -30 - -20 °C 4.1: perchloric acid / 18 h 5.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C 5.2: 12 h / 20 °C 5.3: 2 h / 55 - 65 °C

Reference： [1]Current Patent Assignee: TOHO UNIVERSITY - US2014/51756, 2014, A1

26
[ 77-95-2 ]
[ 39856-08-1 ]
1-O-[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]
1,3-O-bis[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]
1,4-O-bis[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]
1,3,4-O-tris[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine In dichloromethane at 0 - 20℃;

Reference： [1]Sinisi, Valentina; Boronova, Katarina; Colomban, Silvia; Navarini, Luciano; Berti, Federico; Forzato, Cristina [European Journal of Organic Chemistry, 2014, vol. 2014, # 6, p. 1321 - 1326]

27
[ 77-95-2 ]
[ 39856-08-1 ]
1-O-[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]
[ 882535-29-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0 - 20℃;

Reference： [1]Sinisi, Valentina; Boronova, Katarina; Colomban, Silvia; Navarini, Luciano; Berti, Federico; Forzato, Cristina [European Journal of Organic Chemistry, 2014, vol. 2014, # 6, p. 1321 - 1326]

28
[ 77-95-2 ]
[ 39856-08-1 ]
1,3,4-O-tris[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 25h;

Reference： [1]Sinisi, Valentina; Boronova, Katarina; Colomban, Silvia; Navarini, Luciano; Berti, Federico; Forzato, Cristina [European Journal of Organic Chemistry, 2014, vol. 2014, # 6, p. 1321 - 1326]

29
[ 77-95-2 ]
[ 906-33-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: CSA / methanol / 45 h / 85 °C / Reflux; Inert atmosphere 2.1: potassium hydroxide / tetrahydrofuran / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride / 1,2-dichloro-ethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere 4.2: 6 h / 20 °C / Molecular sieve; Inert atmosphere 5.1: boron trichloride; pentamethylbenzene, / dichloromethane / 3 h / -40 - 0 °C / Inert atmosphere
	Multi-step reaction with 7 steps 1.1: CSA / methanol / 45 h / 85 °C / Reflux; Inert atmosphere 2.1: 1H-imidazole / N,N-dimethyl-formamide / 25 h / 20 °C / Inert atmosphere 3.1: potassium hydroxide / tetrahydrofuran / 1.25 h / 20 °C / Inert atmosphere 4.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 5.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 13 h / 20 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride / 1,2-dichloro-ethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere 6.2: 6 h / 20 °C / Molecular sieve; Inert atmosphere 7.1: boron trichloride; pentamethylbenzene, / dichloromethane / 3 h / -40 - 0 °C / Inert atmosphere

Reference： [1]Oyama, Kin-Ichi; Watanabe, Noriyuki; Yamada, Tomomi; Suzuki, Masako; Sekiguchi, Yukiko; Kondo, Tadao; Yoshida, Kumi [Tetrahedron, 2015, vol. 71, # 20, p. 3120 - 3130]
[2]Oyama, Kin-Ichi; Watanabe, Noriyuki; Yamada, Tomomi; Suzuki, Masako; Sekiguchi, Yukiko; Kondo, Tadao; Yoshida, Kumi [Tetrahedron, 2015, vol. 71, # 20, p. 3120 - 3130]

30
[ 77-95-2 ]
[ 39856-08-1 ]
1-O-[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]
1-O-[3,4-(dimethoxy)cinnamoyl]quinic acid [ No CAS ]
[ 88909-07-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 20℃; for 48h;

Reference： [1]Sinisi, Valentina; Boronov, Katarna; Colomban, Silvia; Navarini, Luciano; Berti, Federico; Forzato, Cristina [European Journal of Organic Chemistry, 2014, vol. 2014, # 6, p. 1321 - 1326]

31
[ 77-95-2 ]
[ 39856-08-1 ]
1-O-[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]
1,3,4-O-tris[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]
1,3-O-bis[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]
1,4-O-bis[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 42 %Spectr. 2: 38 %Spectr. 3: 8 %Spectr. 4: 12 %Spectr.	With dmap; triethylamine In dichloromethane at 20℃;

Reference： [1]Sinisi, Valentina; Boronov, Katarna; Colomban, Silvia; Navarini, Luciano; Berti, Federico; Forzato, Cristina [European Journal of Organic Chemistry, 2014, vol. 2014, # 6, p. 1321 - 1326]

32
[ 77-95-2 ]
[ 39856-08-1 ]
1,3,4-O-tris[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 25h;

Reference： [1]Sinisi, Valentina; Boronov, Katarna; Colomban, Silvia; Navarini, Luciano; Berti, Federico; Forzato, Cristina [European Journal of Organic Chemistry, 2014, vol. 2014, # 6, p. 1321 - 1326]

33
[ 77-95-2 ]
[ 39856-08-1 ]
1,3,4-O-tris[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]
1,3-O-bis[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]
1,4-O-bis[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 63 %Spectr. 2: 28 %Spectr. 3: 9 %Spectr.	With dmap; triethylamine In dichloromethane at 20℃;

Reference： [1]Sinisi, Valentina; Boronov, Katarna; Colomban, Silvia; Navarini, Luciano; Berti, Federico; Forzato, Cristina [European Journal of Organic Chemistry, 2014, vol. 2014, # 6, p. 1321 - 1326]

34
[ 77-95-2 ]
[ 1965-09-9 ]
[ 123-31-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 71% 2: 7%	With Amberlyst-15; air In toluene at 100℃; for 24h;
	Multi-step reaction with 2 steps 1: Amberlyst-15 / acetonitrile / 24 h / 50 °C 2: Amberlyst-15 / toluene / 17 h / 100 °C

Reference： [1]Assoah, Benedicta; Veiros, Luis F.; Afonso, Carlos A. M.; Candeias, Nuno R. [European Journal of Organic Chemistry, 2016, vol. 2016, # 22, p. 3856 - 3861]
[2]Assoah, Benedicta; Veiros, Luis F.; Afonso, Carlos A. M.; Candeias, Nuno R. [European Journal of Organic Chemistry, 2016, vol. 2016, # 22, p. 3856 - 3861]

35
[ 77-95-2 ]
[ 1965-09-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Amberlyst-15; air / toluene / 24 h / 100 °C 2: Amberlyst-15 / toluene / 144 h / 100 °C
	Multi-step reaction with 3 steps 1: sodium hypochlorite solution; sulfuric acid / water / 3 h / 20 °C 2: Amberlyst 15 / toluene / 1.5 h / 100 °C 3: Amberlyst-15 / toluene / 144 h / 100 °C
	Multi-step reaction with 3 steps 1: sodium hypochlorite solution; sulfuric acid / water / 3 h / 20 °C 2: Amberlyst-15 / 1,4-dioxane / 0.08 h / 100 °C 3: Amberlyst-15 / toluene / 144 h / 100 °C

Multi-step reaction with 3 steps 1: Amberlyst-15 / acetonitrile / 24 h / 50 °C 2: Amberlyst-15 / toluene / 17 h / 100 °C 3: Amberlyst-15 / toluene / 144 h / 100 °C

Reference： [1]Assoah, Benedicta; Veiros, Luis F.; Afonso, Carlos A. M.; Candeias, Nuno R. [European Journal of Organic Chemistry, 2016, vol. 2016, # 22, p. 3856 - 3861]
[2]Assoah, Benedicta; Veiros, Luis F.; Afonso, Carlos A. M.; Candeias, Nuno R. [European Journal of Organic Chemistry, 2016, vol. 2016, # 22, p. 3856 - 3861]
[3]Assoah, Benedicta; Veiros, Luis F.; Afonso, Carlos A. M.; Candeias, Nuno R. [European Journal of Organic Chemistry, 2016, vol. 2016, # 22, p. 3856 - 3861]
[4]Assoah, Benedicta; Veiros, Luis F.; Afonso, Carlos A. M.; Candeias, Nuno R. [European Journal of Organic Chemistry, 2016, vol. 2016, # 22, p. 3856 - 3861]

36
[ 141-79-7 ]
[ 77-95-2 ]
C₁₃H₁₈O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53.92%	With toluene-4-sulfonic acid; In toluene; at 150℃; for 4h;	D-<strong>[77-95-2](-)-Quinic acid</strong> (20.0 g, 0.10 mol) was sequentially added to a 500 ml jar.Toluene (120 ml), methyl isobutylene ketone (100.0 ml), p-toluenesulfonic acid monohydrate (2.0 g, 0.01 mol), and the temperature was increased to reflux (outer bath 150C). Turbid fluid,After refluxing, the water was separated for 2 hours and the reaction was continued for 2 hours. The system became clear with a small amount of yellow insoluble material stuck to the bottle wall and the reaction was monitored by TLC (DCM: MeOH = 10:1). The mixture was concentrated under reduced pressure at 50 C. H2O (80.0 ml) was added to the residue, adjusted to pH 7-8 with saturated NaHCO 3 , and the aqueous phase was extracted with EA (100.0 ml×2).The combined organic phases were washed with brine (100.0 ml), dried over anhydrous Na2SO4, filtered and concentrated to give 23.70 g of a yellow solid. Recrystallize from ethyl acetatepetroleum ether, crystallize overnight, crystallize at 0C for 2 h, and filter by suction.The filter cake was washed with petroleum ether and the filter cake was dried in vacuo to give 13.71 g of white crystals, Intermediate 3-4a. Yield: 53.92%.
53.92%	With toluene-4-sulfonic acid; In toluene; for 4h;Reflux;	<strong>[77-95-2]D-(-)-quinic acid</strong> (20.0 g, 0.10 mol) was sequentially added to a 500 ml single-mouth bottle.Toluene (120ml),Methyl isobutene methanone(100.0ml),P-toluenesulfonic acid monohydrate (2.0 g, 0.01 mol),After heating up to reflux, the water separator,The system is yellow turbid,After refluxing, water is separated for 2 hours.The reflux reaction was continued for 2 h. The system became clear,A small amount of yellow insoluble matter was applied to the wall of the bottle, and the reaction was completely monitored by TLC.Concentrated under reduced pressure at 50 C, H2O (80.0 ml) was added to the residue,Adjust the pH to 7-8 with saturated NaHCO3.The aqueous phase was extracted with dichloromethane (100.0 mL×2).The organic phases were combined and washed with brine (100.0 mL).Dry anhydrous Na2SO4,Filter and concentrate,Obtained 23.70 g of a yellow solid.Recrystallization from ethyl acetate petroleum ether system,Crystallization overnight,Crystallization at 0 C for 2 h,Filtering,The filter cake was vacuum dried to give 13.71 g of white crystals.Intermediate 3-4a. Yield: 53.92%.

Reference： [1]Patent: CN108003027,2018,A .Location in patent: Paragraph 0158; 0159; 0160; 0161
[2]Patent: CN108484491,2018,A .Location in patent: Paragraph 0184; 0185; 0186; 0187

37
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 77-95-2 ]
2C₇H₁₁O₆^(1-)*Cd⁽²⁺⁾*0.5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%		A quantity of Cd(NO3)2·4H2O (0.16 g, 0.50 mmol) was dissolved in 3 mL of H2O in a round bottom flask under stirring. Subsequently, d-quinic acid (0.19 g, 1.0 mmol) was added in the solution and the reaction medium was allowed to stir for 15 min. Then, an aqueous solution of KOH was slowly added to adjust the pH of the reaction mixture to a final value of 2.5-3.0. The mixture was left under stirring for 1 h at room temperature. The addition of cold ethanol at 4 C led after a few days to the formation of a white crystalline material at the bottom of the vessel. The crystalline product was isolated by filtration and dried in the air. The yield of the reaction was 0.12 g (48%). m.p. 376 C. Anal. Calc. for [Cd(C7H11O6)2]n·n/2H2O (1) (CdC14H23O12.5), Mr 503.72: C: 33.35, H: 4.56. Found: C: 33.14, H: 4.56%.

Reference： [1]Inorganica Chimica Acta,2018,vol. 482,p. 364 - 374

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	77-95-2	MDL No. :	MFCD00003864
Formula :	C₇H₁₂O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AAWZDTNXLSGCEK-LNVDRNJUSA-N
M.W :	192.17	Pubchem ID :	6508
Synonyms :	Chinic acid;Kinic acid;Quinic acid

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.86
Num. rotatable bonds :	1
Num. H-bond acceptors :	6.0
Num. H-bond donors :	5.0
Molar Refractivity :	40.11
TPSA :	118.22 Å²

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-9.15 cm/s

Log Po/w (iLOGP) :	0.37
Log Po/w (XLOGP3) :	-2.37
Log Po/w (WLOGP) :	-2.32
Log Po/w (MLOGP) :	-2.14
Log Po/w (SILICOS-IT) :	-1.82
Consensus Log Po/w :	-1.66

[ CAS No. 77-95-2 ] {[proInfo.proName]}

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[ 77-95-2 ] Synthesis Path-Upstream 1~2

[ 77-95-2 ] Synthesis Path-Downstream 1~37

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[ 77-95-2 ]

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.56

Log S (ESOL) :	0.53
Solubility :	648.0 mg/ml ; 3.37 mol/l
Class :	Highly soluble
Log S (Ali) :	0.43
Solubility :	512.0 mg/ml ; 2.66 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	2.08
Solubility :	23000.0 mg/ml ; 120.0 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.34

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P262-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H317-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 77-95-2 ] {[proInfo.proName]}

Quality Control of [ 77-95-2 ]

Related Doc. of [ 77-95-2 ]

Product Details of [ 77-95-2 ]

Calculated chemistry of [ 77-95-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 77-95-2 ]

Application In Synthesis of [ 77-95-2 ]

[ 77-95-2 ] Synthesis Path-Upstream 1~2

[ 77-95-2 ] Synthesis Path-Downstream 1~37

Related Functional Groups of [ 77-95-2 ]

Aliphatic Cyclic Hydrocarbons

Alcohols

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 77-95-2 ]