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CAS No. : | 4049-33-6 | MDL No. : | MFCD00069790 |
Formula : | C13H18O9 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MJOQJPYNENPSSS-XQHKEYJVSA-N |
M.W : | 318.28 | Pubchem ID : | 2817255 |
Synonyms : |
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.69 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 9.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 68.72 |
TPSA : | 114.43 Ų |
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) : | -8.4 cm/s |
Log Po/w (iLOGP) : | 2.83 |
Log Po/w (XLOGP3) : | -0.23 |
Log Po/w (WLOGP) : | -0.3 |
Log Po/w (MLOGP) : | -0.16 |
Log Po/w (SILICOS-IT) : | -0.04 |
Consensus Log Po/w : | 0.42 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.14 |
Solubility : | 23.0 mg/ml ; 0.0724 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.72 |
Solubility : | 6.13 mg/ml ; 0.0193 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.37 |
Solubility : | 135.0 mg/ml ; 0.424 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 4.34 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With hydrogen bromide; acetic acid In dichloromethane for 4.5 h; Inert atmosphere | A solution of 13.2 g (0.162 mol) HBr in 30percent acetic acid was added at –5°C under argon to a solution of 17.1 g (0.054 mol) of compound 1 in 100 mL of anhydrous dichloromethane. The reaction mixture was stirred at 5°C for 1.5 h and then an additional 3 h at 20°C. Reaction progress was monitored by TLC, eluent ethyl acetate–hexane, 1 : 1. When the reaction was complete, the mixture was cooled to 0°C and diluted with cold dichloromethane, after which pieces of frozen 5percent solution of NaHCO3 were added. The aqueous layer was washed with 3 portions of cold dichloromethane, the combined extracts were dried with anhydrous MgSO4 and concentrated at a reduced pressure. Compound 2 readily decomposed on storage and on column chromatography on silica gel and, therefore, it was used in the subsequent reaction without additional purification. An analytical sample of bromide 2 was prepared by recrystallizaition from ethyl acetate–hexane, 2 : 3. Yield 80percent, mp 102–103°C (mp 101–102°C [50]), Rf 0.67 (ethyl acetate–hexane, 1 : 1). 1H NMR spectrum (CDCl3), δ, ppm (J, Hz): 2.03 s, 2.04 s, 2.06 s (9H, acetyl groups), 3.58 d.d (1H, H5 , J4,5a = 8.7, J5,5b = 12.0), 4.17 d.d (1H, H5b, J4,5b = 5.0, J5b,5a = 12.0), 4.96 d.d.d (1H, H4, J4,5 = 8.6, J4,5b = 5.2), 5.04 t (1H, H2, J2,3 = 7.9), 5.18 t (1H, H3, J3,4 = 7.9), 5.34 d (1H, H1, J1,2 = 4.2). 13C NMR spectrum (CDCl3), δC, ppm: 20.70, 20.73, 20.76 [C(O)OCH3], 65.74 (C5), 68.25 (C4), 69.15 (C3), 72.03 (C2), 80.60 (C1), 169.62, 169.79, 169. 88 [C(O)OCH3]. Mass spectrum (MALDI TOF), m/z: 340.12 [M + H]+ (calculated for C11H16BrO7: 340.09). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In 1,2-dichloro-ethane; | EXAMPLE 12 2,3,4-Tri-O-acetyl-D-xylopyranose is obtained in 76% yield from 1,2,3,4-<strong>[4049-33-6]tetra-O-acetyl-β-D-xylopyranose</strong> according to Procedure A, by carrying out the reaction for 1.5 hours, in refluxing 1,2-dichloroethane. |
72% | In methanol; | EXAMPLE 13 2,3,4-Tri-O-acetyl-D-xylopyranose is obtained in 72% yield from 1,2,3,4-<strong>[4049-33-6]tetra-O-acetyl-β-D-xylopyranose</strong> according to Procedure B, by carrying out the reaction for 2 hours, in methanol at 50 C. |
58% | In methanol; | EXAMPLE 14 2,3,4-Tri-O-acetyl-D-xylopyranose is obtained in 58% yield from 1,2,3,4-<strong>[4049-33-6]tetra-O-acetyl-β-D-xylopyranose</strong> according to Procedure C, by carrying out the reaction for 0.75 hours, in methanol at 50 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With hydrogen bromide; acetic acid; In dichloromethane; for 4.5h;Inert atmosphere; | A solution of 13.2 g (0.162 mol) HBr in 30% acetic acid was added at -5C under argon to a solution of 17.1 g (0.054 mol) of compound 1 in 100 mL of anhydrous dichloromethane. The reaction mixture was stirred at 5C for 1.5 h and then an additional 3 h at 20C. Reaction progress was monitored by TLC, eluent ethyl acetate-hexane, 1 : 1. When the reaction was complete, the mixture was cooled to 0C and diluted with cold dichloromethane, after which pieces of frozen 5% solution of NaHCO3 were added. The aqueous layer was washed with 3 portions of cold dichloromethane, the combined extracts were dried with anhydrous MgSO4 and concentrated at a reduced pressure. Compound 2 readily decomposed on storage and on column chromatography on silica gel and, therefore, it was used in the subsequent reaction without additional purification. An analytical sample of bromide 2 was prepared by recrystallizaition from ethyl acetate-hexane, 2 : 3. Yield 80%, mp 102-103C (mp 101-102C [50]), Rf 0.67 (ethyl acetate-hexane, 1 : 1). 1H NMR spectrum (CDCl3), δ, ppm (J, Hz): 2.03 s, 2.04 s, 2.06 s (9H, acetyl groups), 3.58 d.d (1H, H5 , J4,5a = 8.7, J5,5b = 12.0), 4.17 d.d (1H, H5b, J4,5b = 5.0, J5b,5a = 12.0), 4.96 d.d.d (1H, H4, J4,5 = 8.6, J4,5b = 5.2), 5.04 t (1H, H2, J2,3 = 7.9), 5.18 t (1H, H3, J3,4 = 7.9), 5.34 d (1H, H1, J1,2 = 4.2). 13C NMR spectrum (CDCl3), δC, ppm: 20.70, 20.73, 20.76 [C(O)OCH3], 65.74 (C5), 68.25 (C4), 69.15 (C3), 72.03 (C2), 80.60 (C1), 169.62, 169.79, 169. 88 [C(O)OCH3]. Mass spectrum (MALDI TOF), m/z: 340.12 [M + H]+ (calculated for C11H16BrO7: 340.09). |
With hydrogen bromide; acetic acid; at 0℃; for 2h;Inert atmosphere; | General procedure: The stirring solutions of compounds 1f-j at 0 C were treated with 33% HBr solution in glacial acetic acid under anhydous condition. The reation mixture was further stirred for 2 h at 0 C. After completion of reaction (monitored by TLC), the reaction mixtures were neutralized with saturated NaHCO3 solution followed by extraction in dichloromethane. The organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford compounds 2f-j. Because of low stability at room temperature, all the developed bromo-sugars 2f-j was subsequently utilized for the synthesis of sugar azides 3f-j without further purification. | |
With hydrogen bromide; acetic acid; In dichloromethane; at 0 - 20℃; for 3h; | General procedure: HBr (33 % wt in acetic acid) was added dropwise to a cooled solution (0 C) of the peracetylated saccharide in dichloromethane (10 mL) and stirred for 3 h at rt. Ice water (50 mL) was added to the mixture and the aqueous phase was extracted with dichloromethane (3 x 50 mL). The combined organic layers were washed with 0.5 % Na2S2O3 (1 x 75 mL), sat. NaHCO3 (3 x 75 mL), brine (1 x 75 mL) and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product crystallized from diethylether/pentane to afford the halogenated substrate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With indium(III) bromide; In dichloromethane; at 20℃; for 2h; | General procedure: To a solution of peracetylated aldose (0.1mmol) in CH2Cl2 (2 mL) were added thiophenolor selenophenol (0.12mmol) and InBr3 (3mg, 0.01mol). The reaction mixture was allowedto stir for 2 h at room temperature. After completion as monitored by TLC, the reactionmixture was concentrated. The resultant residue was subjected to flash chromatograph togive the goal products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium acetate; at 140℃; for 4h; | (a) Place anhydrous sodium acetate (27.3g, 333.3mmol) in a 100mL round bottom flask, add acetic anhydride (150mL), reflux at 140C, and after all the solids in the flask are dissolved, add compound 1 (5.0g, 66.6mmol), continue to reflux for 4h. After the completion of the reaction detected by TLC, the solution was poured into a mixture of ice and water, and stirring was continued for 1 h. During this period, a large amount of white crystals were precipitated. After filtration under reduced pressure, a white solid was obtained, which was recrystallized with methanol to obtain a white solid compound 2 (10.2g). Yield 97%. |
30.02 g | With sodium acetate; for 1h;Reflux; | (1) To a 250mL three-necked flask were successively added 0.13mol dried D-xylose, 0.67mol acetic anhydride, anhydrous sodium acetate 36.59mmol, fitted with reflux condenser, mechanical stirring, electric heating heating jacket slightly After dissolving,Remove the heating device, continue stirring until the solid was dissolved completely clarified, cooled to room temperature. Then add 30mmol of anhydrous sodium acetate, the device into the oil bath, heated to reflux for 1h, TLC (developing solvent: V petroleum ether: V ethyl acetate = 1: 1) to monitor the reaction was complete, hot reaction solution was poured into 400mL After stirring in ice water, a large amount of solid precipitated immediately, suction filtered, and the filter cake was washed several times with distilled water to obtain 35.02 g of acetyl-protected D-xylose with a yield of 82.6%. Recrystallization from aqueous methanol (V methanol: V water = 1: 2) yielded 30.02 g of pure acetyl-protected D-xylose. Directly used for the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With pyridine; dmap; at 0 - 20℃; for 4.33333h;Inert atmosphere; | The DMAP catalyst was added to a solution of 30.0 g (0.2 mol) D-(+)-xylose in 150 mL of anhydrous pyridine, after which 81.7 g (0.8 mol) of acetic anhydride was added dropwise with vigorous stirring at 0C under argon over the course of 20 min. The reaction mixture was stirred at 0C for 1 h and then for an additional 3 h at 20C. The reaction progress was monitored by TLC in ethyl acetate-hexane, 1 : 1. When the reaction was complete, the mixture was cooled to 0C and diluted with ethyl acetate. The organic phase was treated in succession with 5% H2SO4 and concentrated solutions of NaHCO3 and NaCl, and then dried with anhydrous MgSO4 and concentrated at a reduced pressure. The resulting amorphous substance was purified by column chromatography on silica gel, eluent ethyl acetate- hexane, 1 : 9. A 1.5 : 1 mixture of the β and α anomers was obtained. β-Anomer 1 was isolated as colorless crystals after double recrystallization of the anomers mixture from ethanol. Yield 57%, mp 127-128C, [α]D20 -38.7 (c 2.3, CH2Cl2) {mp 126-127C, [α]D20 -38.5 (c 2.3, CH2Cl2) [49], Rf 0.56 (ethyl acetate- hexane, 1 : 1). 1H NMR spectrum (CDCl3), δ, ppm (J, Hz): 2.02 s, 2.03 s, 2.04 s, 2.06 s (12H, acetyl groups), 3.52 d.d (1H, H5 , J4,5a = 8.5, J5,5b = 11.9), 4.12 d.d (1H, H5b, J4,5b = 5.0, J5b,5a = 12.0), 4.91 d.d.d (1H, H4, J4,5 = 8.4, J4,5b = 4.8), 4.99 t (1H, H2, J2,3 = 7.8), 5.18 t (1H, H3, J3,4 = 7.8), 5.34 d (1H, H1, J1,2 = 8.7). 13C NMR spectrum (CDCl3), δC, ppm: 20.65, 20.68, 20.71, 20.74 [C(O)OCH3], 65.69 (C5), 68.25 (C4), 69.08 (C3), 71.64 (C2), 80.34 (C1), 169.30, 169.58, 169.71, 169. 85 [C(O)OCH3]. Mass spectrum (MALDI TOF), m/z: 341.17 [M + Na]+ (calculated for C13H18O9Na: 341.12). |
With O-(3-sulfopropyl)-functionalized nano γ-Al2O3; In neat (no solvent); at 20 - 50℃; for 0.666667h; | General procedure: To a stirred suspension of d-glucose (1 mmol) in acetic anhydride (5.1 mmol) at room temperature was added sulfonic acid functionalized nano γ-Al2O3 (50 mg). The mixture was stirred at 50 C for 40 min. After completion of the reaction (TLC), the mixture was put into diethyl ether (50 mL) and microporous filtration (microporous membrane: PVDF, pore sizes: 0.1 μm). The solvents were removed under reduced pressure and the crude product was passed through a short pad of silica to give pure acetylated product 2c. The catalyst was washed with absolute EtOH, dried and re-used for a consecutive run under the same reaction conditions. | |
With iodine; at 50℃; for 0.0833333h;Microwave irradiation; | General procedure: To a 10.0 mL round bottom flask, D-glucose (2.0 mmol) and acetic anhydride (12.0 mmol, 1.2 equiv. per OH) in the IL400 (2.0mL) was added I2 (0.05 mmol) at room temperature. Then themixture was heated to 50 C under MW irradiation (200 W) until the TLC analysis showed that the reaction was complete.Then the reaction mixture was cooled to room temperature,and toluene (2.0 mL × 3) was added. The mixture was vigorously stirred for several minutes and then kept stationary. The upper toluene layer containing the product was collected. Toluene was removed by a rotary evaporator, and the crude product was purified by recrystallization in ethyl alcohol. The desired peracetylated sugars were obtained in 90%-99% yields. The bottom phase was the ionic liquid containing the I2 catalyst and produced acetic acid. The I2/IL400 system was reused after the removal of the acetic acid under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen bromide; acetic acid; In dichloromethane; at 0℃; for 24h;Inert atmosphere; | Example 9 Synthesis of the sodium β-D-xyloside 6,8-difluoro-7-hydroxycoumarin-4-methanesulfonate substrate (12) Bromination Of The Protected Sugar: Under a nitrogen atmosphere, 500 mg of aceto-β-D-xylopyranose and 10 mL of DCM are introduced into a flask. The mixture is cooled to 0 C. and then 5 equivalents of hydrobromic acid in solution at 33% in acetic acid are added dropwise. After 24 hours of reaction, 15 mL of DCM are added, the mixture is cooled to 0 C. and then 20 mL of ice water are added. After separation of both phases, the organic phase is washed three times with a saturated NaHCO3 solution and three times with water. After drying on MgSO4 and filtration, the filtrate is evaporated under reduced pressure. The obtained acetobromo-α-D-xylose is then directly introduced into the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 14% 2: 15% | Stage #1: 1,7-Dihydroxynaphthalene With pyridine; dmap; polystyrene resin-C6H4-pCH2NHC(O)CH2CH2C(O)Cl In dichloromethane at 20℃; Stage #2: tetra-O-acetyl-β-D-xylopyranose With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.75h; Stage #3: With sodium methylate In methanol; dichloromethane at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 16% 2: 9% | Stage #1: 1,3-dihydroxynaphthalene With pyridine; dmap; polystyrene resin-C6H4-pCH2NHC(O)CH2CH2C(O)Cl In dichloromethane at 20℃; Stage #2: tetra-O-acetyl-β-D-xylopyranose With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.75h; Stage #3: With sodium methylate In methanol; dichloromethane at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With boron trifluoride diethyl etherate; triethylamine In dichloromethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With boron trifluoride diethyl etherate; triethylamine; In dichloromethane;Inert atmosphere; | From 1,2,3,4-tetra-O-acetyl-β-d-xylopyranose (3d) (3.18 g, 10 mmol) propargyl alcohol (0.84 mL, 15 mmol) and BF3-Et2O (3.52 mL, 25 mmol).CommentWhite solid; (2.40 g, 76%); mp 114-116 C. 1H NMR (300 MHz, CDCl3): δH 5.14-5.20 (m, 1H), 4.94-5.00 (m, 3H), 4.85-4.91 (m, 1H), 4.68 (d, J 6.6 Hz, 1H), 4.16-4.17 (m, 1H), 4.18-4.21 (m, 3H), 3.40-3.47 (m, 1H), 2.14 (t, J 4.8 Hz, 1H), 2.07 (s, 3H), 2.06 (s, 3H), 2.04 (s, 3H). 13C NMR (75 MHz, CDCl3): δC 170.1 169.8, 169.5, 155.7, 152.7, 129.0, 125.6, 123.0, 118.0, 116.7, 99.5, 71.2, 70.5, 69.3, 68.8, 62.1, 61.9, 20.6, 20.8 (2c). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With 1H-imidazole; In dichloromethane; for 12.5h;Cooling with ice; | A solution of 0.75 g of xylose (5 nmol), 2.84 mE (30mmol) of acetic anhydride, and 2.04 g (30 mmol) of imidazole in 700 mE of dichioromethane was placed in an ice bath for 30 mm and then stirred for 12 hours. The reactionwas then quenched by the addition of methanol and stirredin ice for 30 mm. The mixture was diluted with dichloromethane, adjusted to a neutral pH using HCl, andextracted with Et20. The usual work-up and column chromatography afforded acetylated xylose (1.50 g, 94%) as awhite solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Under an argon atmosphere, 5 g (15.7 mM) of vacuum-dried tetra-O-acetyl-β-D-xylopyranoside and 100 ml of methylene chloride were added to 2 g of dried molecular sieve 4A, and the resultant was agitated for 10 to 30 minutes. The product was cooled to 5C to 8C, 16 ml of a solution of 1M tin chloride in methylene chloride was added dropwise thereto, and the mixture was agitated at room temperature for 20 minutes. After the resultant was cooled to -10C, 16 ml of a solution of 4.69 g (15.7 mM) of 3,7,11,15-tetramethylhexadecanol in methylene chloride was added dropwise over about 30 minutes, and agitation was continued in that state for 4 hours. The resulting solution was introduced into a saturated aqueous solution of sodium bicarbonate, and extraction was carried out 3 times with 100 ml of methylene chloride, followed by washing with water. The organic phase was dried over anhydrous sodium sulfate, filtrated, and then concentrated. Subsequently, the mixture was purified by silica gel column chromatography (eluent: a mixed solvent of hexane/ethyl acetate). | ||
To an activated molecular sieve 4A (2 g) under an argon atmosphere,Tetra-O-acetyl-β-D-xylopyranoside (5 g, 15.7 mM) dried under reduced pressure,100 ml of methylene chloride was added,And the mixture was stirred for 10 to 30 minutes.After cooling to 5 to 8 C., 16 ml of a methylene chloride solution of 1 M tin chloride was added dropwise,And the mixture was stirred at room temperature for 20 minutes.After cooling to -10 C.,A solution of 3, 7, 11, 15-tetramethylhexadecanol (4.69 g, 15.7 mM) in 16 ml of methylene chloride was added dropwise over about 30 minutes, and stirring was continued for 4 hours as it was. This solution was poured into a saturated aqueous sodium hydrogencarbonate solution, extracted three times with 100 ml of methylene chloride, and then washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The mixture was then purified by silica gel column chromatography (eluent: hexane-ethyl acetate mixed solvent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Under an argon atmosphere, 318 mg of β-xylose tetraacetate was dissolved in 6 ml of dry methylene chloride, and the solution was cooled to 0C. A solution of 0.12 ml of tin tetrachloride dissolved in 1 ml of methylene chloride was added dropwise thereto, the mixture was agitated at room temperature for 20 minutes, and then cooled to -10C. A solution of 326.6 mg of 5,9,13,17-tetramethyloctadecanol in 1 ml of methylene chloride was added dropwise thereto, and the mixture was agitated for 4 hours. A sodium bicarbonate water was added to the reaction solution and extraction was carried out 3 times with methylene chloride. The extract was washed with water and dried over anhydrous sodium sulfate. After the filtration, the resultant was concentrated, and the concentrate was purified by column chromatography to obtain 93 mg of 1-O-(5,9,13,17-tetramethyloctadecyl)-β-D-xylopyranoside triacetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With boron trifluoride diethyl etherate; triethylamine; In dichloromethane; for 5h;Inert atmosphere; | From per-O-acetyl-β-d-xylopyranose (3d) (0.19 g, 0.60 mmol), fluorescein diol (2) (0.18 g, 0.30 mmol) and BF3·Et2O (23 mmol, 3 mL). Yellow solid (0.18 g, 54%); mp 168-170 C; +49.3 (c 0.2, CHCl3). 1H NMR (300 MHz, CDCl3): δ 2.05 (s, 6H), 2.06 (s, 6H), 2.11 (s, 6H), 3.49-3.56 (q, 2H), 4.13 (d, J = 4.8 Hz, 2H), 4.17 (d, J = 4.8 Hz, 3H), 4.78 (d, J = 4.5 Hz, 1H), 4.94-5.06 (m, 5H), 5.21 (t, J = 6.0 Hz, 2H), 5.72 (d, J = 6.9 Hz, 1H), 6.73 (s, 2H), 6.75 (d, J = 8.7 Hz, 3H), 6.91 (t, J = 6.0 Hz, 2H), 7.24-7.31 (m, 2H), 7.57 (q, J = 9.0 Hz, 3H), 7.65-7.74 (m, 2H), 8.05 (m, 2H), 8.25 (t, J = 6.0 Hz, 2H). 13C NMR (75 MHz, CDCl3): δ 20.4, 20.6, 20.7, 20.8, 62.8, 68.3, 69.5, 71.0, 76.6, 77.0, 77.5, 92.0, 116.4, 117.9, 118.5, 119.4, 124.2, 125.2, 125.6, 126.4, 128.7, 129.0, 130.3, 133.9, 150.3, 150.6, 164.5, 169.0, 169.3, 169.8. Anal. Calcd for C58H52O23: C, 62.36; H, 4.69. Found: C, 62.19; H, 4.88. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With boron trifluoride diethyl etherate; In dichloromethane; at 20℃;Cooling with ice; | 1,2,3,4-Tetra-O-acetyl-β-d-xylopyranose (2) (662 mg, 2.08 mmol) and 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanol (544 μL, 909 mg, 2.49 mmol, 1.2 equiv) were dissolved in CH2Cl2 (8 mL) at room temperature. The stirring solution was cooled in an ice-water bath. BF3·Et2O (385 μL, 443 mg, 3.12 mmol, 1.5 equiv) was added drop wise. The ice-bath was removed and the solution was allowed to warm to room temperature overnight. The reaction was quenched with satd NaHCO3 (10 mL). After separation of the layers the aqueous phase was extracted twice with CH2Cl2 (15 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silica gel flash column chromatography using hexanes-EtOAc as eluent (5:1, v/v) to yield 10 (434 mg, 34%) as a white solid. Rf 0.75 (4:1 hexanes: EtOAc, v/v); mp 94-95 C; 1H NMR (CDCl3, 400 MHz): δ 2.04 (s, 3H, CH3CO), 2.04 (s, 3H, CH3CO), 2.06 (s, 3H, CH3CO), 2.42 (tt, 2H, J2',3' = 18.8 Hz, J1',2' = 6.5 Hz, H-2'), 3.40 (dd, 1H, J5a,5b = 11.8, J4,5a = 8.6 Hz, 5a), 3.79 (dt, 1H, J1'a,1'b = 10.4 Hz, J1'a,2' = 6.7 Hz, H-1'a), 4.07-4.16 (m, 2H, H-1'b and H-5e), 4.52 (d, 1H, J1,2 = 6.6 Hz, H-1), 4.90-4.97 (m, 2H, H2 and H4), 5.16 (pseudo t, 1H, J2,3 = J3,4 = 8.3 Hz, H-3); 13C NMR (CDCl3, 100 MHz,): δ 20.5, 20.6, 20.7, 31.4, 61.3, 62.0, 68.7, 70.3, 71.0, 100.6, 169.4, 169.8, 170.0; 19F NMR (282 MHz, CDCl3): δ -81.3 (CF3), -113.9 (CF2), -122.4 (CF2), -123.3 (CF2), -124.1 (CF2), -126.6 (CF2); HRESIMS m/z: calcd for C19H19O8F13Na [M+Na]+: 645.0765; found: 645.0781; Anal. Calc for C19H19O8F13: C 37.67; H 3.08; found: C 36.75; H 2.96. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 8Synthesis of 1-O-(5,9,13,17-tetramethyloctadec-4-enyl)-D-xylopyranoside triacetate Under a nitrogen atmosphere, 80.0 g (0.251 mol) of β-xylose tetraacetate and 106 g (0.327 mol) of 5,9,13,17-tetramethyloctadec-4-en-1-ol was dissolved in dry acetonitrile (0.30 L), and stirred for 30 min. After the solution was cooled to 0 C., 38 mL (0.30 mol) of boron trifluoride diethyl etherate complex was added. The reaction mixture was allowed to warm up to room temperature while being stirred overnight before addition of 70 mL (0.50 mol) of triethylamine at 0 C. The resulting solution was diluted with ethyl acetate, and washed with water, 3M hydrochloric acid (twice), saturated sodium bicarbonate aqueous solution (twice), and saturated brine, successively, and dried over magnesium sulfate. After filtration, the filtrate was concentrated to obtain 161.95 g of the title compound as a crude product. A part of the crude product was purified by silica gel column chromatography (hexane/ethyl acetate 85:15). The results of NMR analysis of the resulting compound are as shown below.1H-NMR spectrum (400 MHz, CDCl3, TMS) δ: 0.8-0.95 (m, 12H), 1.0-1.8 (m, 24H), 1.85-2.1 (m, 4H), 2.03 (s, 3H), 2.05 (s, 6H), 3.35 (dd, J=9.12 Hz, 1H), 3.45 (m, 1H), 3.80 (m, 1H), 4.11 (dd, J=5, 12 Hz, 1H), 4.47 (d, J=6.8 Hz, 1H), 4.94 (m, 2H), 5.09 (m, 1H), 5.16 (dd, J=8.7, 8.7 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | (b) First activate 200mg of powdered molecular sieve, then place molecular sieve and compound 2 (5.0g) in a round bottom flask, under Ar protection, add anhydrous DCM (50mL) to dissolve the solids, and wait until all the solids are dissolved After that, stir at room temperature for 30 min, then move to 0C, add p-nitrophenol (4.36g, 31.4mmol), the solution gradually turns yellow, then slowly add boron trifluoride ether (11.1mL), and stir at 0C for 4h. After the completion of the reaction was detected by TLC, stirring was continued, saturated aqueous sodium bicarbonate solution was added until no bubbles were generated, DCM (50 mL) was added to extract the organic phase, saturated brine (30 mL) was used to wash the organic phase once, and anhydrous sodium sulfate was added to dry the organic phase. After filtration under reduced pressure, it was concentrated using a rotary evaporator, and the crude product was purified using a silica gel column (200-300 mesh) to obtain a colorless solid compound 3 (2.8 g, 45%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20℃; | Peracetylated xylose 6 (1.16 g, 3.64 mmol) was dissolved in CH2Cl2 (10 mL) and 2-bromoethanol (215 μL, 3.03 mmol) was added. BF3·Et2O (570 μL, 4.49 mmol) was added dropwise to the solution at 0 C. The mixture was allowed to reach rt and stirred for 1.5 h. CH2Cl2 was added and the mixture was washed with water (20 mL) and NaHCO3 (satd aq) (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to yield an off-white solid. Column chromatography (SiO2, 1:25→1:10 EtOAc/CH2Cl2) gave 8 as a white solid (801 mg, 69%). -48 (c 1.2, MeOH); 1H NMR (CDCl3): δ 5.17 (t, 1H, J 8.4 Hz, H-3), 4.92-4.97 (m, 2H, H-2, H-4), 4.55 (d, 1H, J 6.8 Hz, H-1), 4.07-4.17 (m, 2H, H-5e, CH2), 3.77-3.83 (m, 1H, CH2), 3.45-3.48 (m, 2H, CH2), 3.39 (dd, 1H, J 12, 8.4 Hz, H-5a), 2.08, 2.054, 2.047 (s, 3H each, OAc); 13C NMR (CDCl3): δ 170.2, 170.0, 169.7, 100.9, 71.2, 70.5, 69.4, 68.9, 62.2, 30.2, 20.94, 20.91, 20.88; HRMS calcd for C13H19BrO8Na+ [M+Na]: 405.0161; found: 405.0178. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With boron trifluoride diethyl etherate; In dichloromethane; at 0℃; | Peracetylated xylose 6 (383 mg, 1.20 mmol) was dissolved in CH2Cl2 (3 mL) and 2-(2-chloroethoxy)-ethanol (106 μL, 1.00 mmol) was added. BF3·Et2O (190 μL, 1.50 mmol) was added dropwise to the solution at 0 C. The reaction was performed and worked-up as for 8. Column chromatography (SiO2, 1:25 EtOAc/CH2Cl2) gave 9 as a white solid (163 mg, 43%). -49 (c 1.2, CHCl3); 1H NMR (CDCl3): δ 5.16 (t, 1H, J 8.4 Hz, H-3), 4.91-4.97 (m, 2H, H-2, H-4), 4.57 (d, 1H, J 6.8 Hz, H-1), 4.13 (dd, 1H, J 11.6, 5.2 Hz, H-5e), 3.89-3.94 (m, 1H, CH2), 3.72-3.75 (m, 3H, CH2), 3.66-3.70 (m, 2H, CH2), 3.60-3.62 (m, 2H, CH2), 3.37 (dd, 1H, J 11.8, 8.6 Hz, H-5a), 2.06, 2.05, 2.04 (s, 3H each, OAc); 13C NMR (CDCl3): δ 170.2, 170.0, 169.6, 100.8, 71.6, 71.5, 70.9, 70.5, 69.0, 68.8, 62.2, 43.0, 20.91, 20.88; HRMS calcd for C15H23ClO9Na+ [M+Na]: 405.0928; found: 405.0952. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With boron trifluoride diethyl etherate; In dichloromethane; at 0℃; | Peracetylated xylose 6 (383 mg, 1.20 mmol) was dissolved in CH2Cl2 (3 mL) and 2-[2-(2-chloroethoxy)ethoxy]-ethanol (145 μL, 1.00 mmol) was added. BF3·Et2O (190 μL, 1.50 mmol) was added dropwise to the solution at 0 C. The reaction was performed and worked-up as for 8. Column chromatography (SiO2, 1:13→1:5 EtOAc/CH2Cl2) gave 10 as a white solid (260 mg, 61%). -46 (c 0.8, CHCl3); 1H NMR (CDCl3): δ 5.12 (t, 1H, J 8.6 Hz, H-3), 4.86-4.92 (m, 2H, H-2, H-4), 4.52 (d, 1H, J 6.8 Hz, H-1), 4.08 (dd, 1H, J 11.6, 5.2 Hz, H-5e), 3.84-3.89 (m, 1H, CH2), 3.58-3.73 (m, 11H, CH2), 3.33 (dd, 1H, J 12, 8.8 Hz, H-5a), 2.02, 2.01, 1.99 (s, 3H each, OAc); 13C NMR (CDCl3): δ 170.1, 169.9, 169.5, 100.7, 71.42, 71.39, 70.8, 70.7, 70.4, 68.9, 68.7, 62.0, 42.8, 20.79, 20.76; HRMS calcd for C17H27ClO10Na+ [M+Na]: 449.1190; found: 449.1215. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With boron trifluoride diethyl etherate; In dichloromethane; at 20℃; | Peracetylated xylose 6 (119 mg, 0.374 mmol) and 6-acethoxy-2-naphthalenemethanol 28 (53 mg, 0.25 mmol) were dissolved in CH2Cl2 (3 mL) and BF3·Et2O (50 μL, 0.39 mmol) was added dropwise to the solution at rt. After 1 h of stirring, the mixture was neutralized with NEt3 and concentrated. Column chromatography (SiO2, 1:1 EtOAc/heptane) gave 7b as a white amorphous solid (91 mg, 79%). -54 (c 0.6, MeOH); 1H NMR (C6D6): δ 7.50-7.57 (m, 4H, ArH-1, ArH-4, ArH-5, ArH-8), 7.31 (dd, 1H, J 8.5, 1.6 Hz, ArH-7), 7.19 (dd, 1H, J 8.9, 2.3 Hz, ArH-3), 5.37-5.42 (m, 2H, H-1, H-3), 5.06-5.11 (m, 1H, H-4), 4.81, 4.50 (ABq, 1H each, J 12.5 Hz, CH2), 4.45-4.47 (m, 1H, H-2), 3.95 (dd, 1H, J 11.7, 5.1 Hz, H-5e), 3.03 (dd, 1H, J 11.8, 8.6 Hz, H-5a), 1.82, 1.72, 1.70, 1.60 (s, 3H each, OAc); 13C NMR (C6D6): δ 169.8, 169.3, 169.0, 168.5, 149.3, 135.0, 133.9, 131.6, 129.5, 126.6, 126.5, 122.0, 118.9, 99.9, 72.1, 71.4, 70.1, 69.5, 62.2, 20.6, 20.38, 20.35, 20.2. HRMS calcd for C24H26O10Na+ [M+Na]: 497.1424; found: 497.1428. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20℃; | General procedure: Peracetylated xylose 6 (319 mg, 1.00 mmol) and 2-naphthalenemethanol (273 mg, 1.50 mmol) were dissolved in CH2Cl2 (3 mL) and BF3·Et2O (190 μL, 1.50 mmol) was added dropwise to the solution at 0 C. The mixture was allowed to reach rt and stirred for 1.5 h. CH2Cl2 was added and the mixture was washed with water (20 mL) and NaHCO3 (satd aq) (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to yield a white solid. The crude was filtered through a pile of silica, concentrated, and used in the next step without further purification. The crude residue (344 mg) was dissolved in MeOH/CH2Cl2 (1:1, 6 mL) and NaOMe (1 M, 0.3 mL) was added. After 1.5 h of stirring at rt, AcOH (6 mL) was added and the reaction mixture was concentrated to yield a white solid. HPLC gave 2a after lyophilization as a white solid (33 mg, 11%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With boron trifluoride diethyl etherate; triethylamine; In dichloromethane; at 20 - 21℃; for 5h;Inert atmosphere; | General procedure: To a mixture of 4-MU (1.0-6.0 mmol) and glycosyl acetate (1.0-4.0 mmol) under an argon atmosphere, dry solvent was added successively, followed by the corresponding molar equivalents of base and Lewis acid. The mixture was stirred for a set amount of time at a certain temperature (as shown in Tables 1-3). Then, an equal volume of CH2Cl2 was added to dilute the reaction mixture, and the reaction was quenched with saturated aqueous NaHCO3. The organic phase was washed with diluted aqueous NaOH (1 M) until the aqueous phase was a light brownish-yellow or almost colorless, then washed successively with distilled water, saturated aqueous NaCl, dried with anhydrous Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by flash column chromatography (silica gel, 200-300 mesh, PE/EtOAc, 5/2), then the desired product was crystallized from anhydrous ethyl ether and dried, or the crude product was purified by several recrystallizations from ethanol. |
73% | With boron trifluoride diethyl etherate; triethylamine; In dichloromethane; at 20℃; for 5h;Inert atmosphere; | 4-MU (0.352g, 2.00mmol, 1.0e.q.) under argon protectionAnd β-D-xylopyranosyl tetraacetate (1.273 g, 4.00 mmol, 2.0 e.q.)Dry CH2Cl2 (6ml) suspension, add dry Et3N (700μL, 5.00mmol, 2.5eq), BF3.OEt2 (3218μL, 25.00mmol, 12.5eq), stir the reaction at room temperature for 5h, then add 6ml CH2Cl2 to dilute Then, the reaction is stopped with a Na2CO3 solution or a saturated NaHCO3 solution, followed by washing with a dilute NaOH solution until the solution becomes light or alkaline, and then washed with water and saturated brine, and the organic phase is dried with anhydrous Na2SO4. The separated organic phase is concentrated, followed by flash column chromatography (200-300 mesh silica gel, eluted with petroleum ether II / ethyl acetate = 5/2), and the obtained target separation liquid is evaporated to remove solvent. Add anhydrous ether, stir, filter, and recrystallize with absolute ethanol.After drying, white powder 0.633g was obtained.(Yield 73%, labeled as Compound 11, which has the structure shown in Formula 11) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Under an argon atmosphere, 5 g (15.7 mM) of vacuum-dried tetra-O-acetyl-β-D-xylopyranoside and 100 ml of methylene chloride were added to 2 g of dried molecular sieve 4 A, and the resultant was agitated for 10 to 30 minutes. The product was cooled to 5 C. to 8 C., 16 ml of a solution of 1M tin chloride in methylene chloride was added dropwise thereto, and the mixture was agitated at room temperature for 20 minutes. After the resultant was cooled to -10 C., 16 ml of a solution of 4.69 g (15.7 mM) of 3,7,11,15-tetramethylhexadecanol in methylene chloride was added dropwise over about 30 minutes, and agitation was continued in that state for 4 hours. The resulting solution was introduced into a saturated aqueous solution of sodium bicarbonate, and extraction was carried out 3 times with 100 ml of methylene chloride, followed by washing with water. The organic phase was dried over anhydrous sodium sulfate, filtrated, and then concentrated. Subsequently, the mixture was purified by silica gel column chromatography (eluent: a mixed solvent of hexane/ethyl acetate). (0312) The resulting 1-O-(3,7,11,15-tetramethylhexadecyl)-β-D-xylopyranoside triacetate was dissolved in 5.5 ml of methanol, and 2.5 ml of 0.05M sodium methylate was added thereto. After the mixture was agitated at room temperature for 4.5 hours, the equal amount of 1N hydrochloric acid was added for neutralization. After the solution was concentrated, the concentrate was purified by silica gel column chromatography (eluent: a mixed solvent of chloroform/methanol), and the resultant was dried under reduced pressure to obtain the title compound, 1-O-(3,7,11,15-tetramethylhexadecyl)-β-D-xylopyranoside as a white waxy solid. 1H-NMR measurement demonstrated that contamination by 1-O-(3,7,11,15-tetramethylhexadecyl)-α-D-xylopyranoside did not take place. (0313) 1H-NMR spectrum (270 MHz, CDCl3, TMS) δ: 0.8-0.9 (m, 15H), 0.95-1.75 (m, 24H), 2.71 (brs, 1H, OH), 2.87 (brs, 1H, OH), 3.26 (brs, 1H, OH), 3.37 (dd, J=8.0, 11.9 Hz, 1H), 3.4-3.65 (m, 3H), 3.74 (m, 1H), 3.90 (m, 1H), 4.04 (dd, J=4.2, 11.9 Hz, 1H), 4.37 (d, J=6.0 Hz, 1H). (0314) 1-O-(3,7,11,15-tetramethylhexadecyl)-β-D-xylopyranoside synthesized was also referred to below as β-XP. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With boron trifluoride diethyl etherate In dichloromethane |
[ 64913-16-2 ]
(2S,3S,4R,5R,6S)-6-Methyltetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
Similarity: 1.00
[ 83-87-4 ]
(3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
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[ 27821-10-9 ]
(2R,3R,4R,5S,6S)-6-Methyltetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
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[ 24332-95-4 ]
(3S,4R,5R,6S)-6-Methyltetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
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[ 64913-16-2 ]
(2S,3S,4R,5R,6S)-6-Methyltetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
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[ 62446-93-9 ]
(3R,4S,5R)-Tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
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[ 496924-55-1 ]
(2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl acetate
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[ 83-87-4 ]
(3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
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[ 27821-10-9 ]
(2R,3R,4R,5S,6S)-6-Methyltetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
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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 |
Sorry,this product has been discontinued.
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