Category: 83-87-4

83-87-4, (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

83-87-4, This compound was prepared following a procedure adopted in similar cases.20 beta-d-Glucose pentaacetate (3.83 g, 9.82 mmol) and BF3¡¤Et2O (1.24 mL, 9.82 mmol), previously dissolved in 15 mL of dry dichloromethane, were added under a nitrogen atmosphere to a solution of (4-iodo-phenoxy)-trimethylsilane 17 (2.39 g, 8.18 mmol) in 15 mL of CH2Cl2 kept at room temperature. After 12 h the reaction mixture was washed with saturated aqueous bicarbonate 50 mL¡Á3 and brine 50 mL¡Á2 and dried over anhydrous Na2SO4. Evaporation of the solvent at reduced pressure gave the crude product that was purified by column chromatography over silica gel, using a mixture of petroleum ether/ethyl acetate 6:4 as eluent obtaining 10a as a white solid (3.65 g, 81% yield). (Found: C, 43.61, H, 4.20. C20H23IO10 requires C, 43.65, H, 4.21); Rf (petroleum ether/ethyl acetate 6:4) 0.49; mp 144-145 C (methanol). deltaH (CDCl3, 400 MHz): 1.99 (3H, s, CH3), 2.00 (3H, s, CH3), 2.01 (3H, s, CH3), 2.03 (3H, s, CH3), 3.78-3.86 (1H, m, CH), 4.12 (1H, dd, J 12.3, 2.4 Hz, CH2), 4.24 (1H, dd, J 12.3, 5.4 Hz, CH2), 5.00 (1H, d, J 7.6 Hz, anomeric CH), 5.11 (1H, t, J 9.6 Hz, CH), 5.18-5.29 (2H, m, 2CH), 6.70-6.75 (2H, app d, J 9.0 Hz, Ph), 7.52-7.57 (2H, app d, J 9.0 Hz, Ph). deltaC (CDCl3, 100 MHz) 20.5 (CH3), 20.6 (2CH3), 20.8 (CH3), 61.8 (CH2), 68.1 (CH, glucose ring), 71.0 (CH, glucose ring), 72.0 (CH, glucose ring), 72.5 (CH, glucose ring), 86.2 (C-I, Ph), 98.9 (anomeric CH), 119.2 (C, Ph), 138.4 (C, Ph), 156.6 (C, Ph), 169.2 (CO), 169.3 (CO), 170.2 (CO), 170.5 (CO). numax/cm-1 (KBr): 818, 1041, 1224 (s, C-O-C), 1432, 1485, 1587, 1750 (s, CO), 2961.

83-87-4 (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 10293747, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Hassan Omar, Omar; Babudri, Francesco; Farinola, Gianluca M.; Naso, Francesco; Operamolla, Alessandra; Pedone, Adriana; Tetrahedron; vol. 67; 2; (2011); p. 486 – 494;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.83-87-4,(3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate,as a common compound, the synthetic route is as follows.,83-87-4

To a solution of D-glucose (3.00 g, 16.6 mmol) in dry pyridine (33 mL) at 0 C under a nitrogen atmosphere was slowly added acetic anhydride (31.5 mL, 333 mmol). The reaction mixture was stirred at 0C for 1 h before a catalytic amount of DMAP (200 mg,1.67 mmol) was added. As the reaction mixture was allowed to reach rt, it becomes slightly exothermic. After 6 h, the clear yellow mixture was slowly poured into rapidly stirred ice-water (125 mL),giving a sticky solid. After EtOAc extraction (345 mL), evaporation of the solvent and co-evaporation with dry toluene (320 mL), peracetylated glucose was obtained as a yellow solid (5.84 g, 90%). A solution of pentaacetyl-D-glucopyranose (2.00 g, 5.1 mmol) in DCM(20 mL) was stirred in an ice bath while HBr/HOAc (6 mL, 45 wt %) was added drop-wise. After an hour, the solution was washed with ice-water and cold saturated NaHCO3 solution, dried over MgSO4, and concentrated to leave the glucosyl bromide as a pale yellow oil (1.83 g).

As the paragraph descriping shows that 83-87-4 is playing an increasingly important role.

Reference£º
Article; Vo, Quan V.; Trenerry, Craige; Rochfort, Simone; Hughes, Andrew B.; Tetrahedron; vol. 69; 41; (2013); p. 8731 – 8737;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

83-87-4, (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

83-87-4, (1) Weigh the hydroxyacetylated glucose intermediate (35 g, 89.7 mmol) obtained in step (1)Triethylamine (4.75 g, 46.9 mmol),3,4-dimethoxyphenol (20G, 129.7 mmol),Sequentially added to dichloromethane (250mL) at 0 C conditions,Boron trifluoride ethyl ether silica gel (50 g)Then naturally warmed to room temperature for 9 hours; then the organic phaseWashed successively with saturated sodium bicarbonate, saturated brine, filtered,Concentrated, recrystallized from anhydrous methanol,A yield of 94.3% was obtained for 40.95 g of glycoside intermediate substituted at the position of glucose anomeric carbon.

As the paragraph descriping shows that 83-87-4 is playing an increasingly important role.

Reference£º
Patent; Dongying Daoyi Bio-pharmaceutical Technology Co., Ltd.; Weifang Hongnuo He Tai New Materials Technology Co., Ltd.; Li Fahui; (5 pag.)CN107151260; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.83-87-4,(3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate,as a common compound, the synthetic route is as follows.

83-87-4, To a solution of 30.0 g (76.8 mmol, 1 eq.) penta-O-acetyl-alpha/beta-D-glucopyranose (1) cooled to 0 C in 150 mL abs. dichloromethane 15.2 g (122 mmol, 1.6 eq.) thiocresol and 14.0 mL BF3Et2O (100 mmol, 1.3 eq.) were added slowly. After the addition, the solution was allowed to warm to room temperature and was stirred 24h. The organic phase was neutralized with sat.aq. NaHCO3 (3 ¡Á 70 mL), water (2 ¡Á 70 mL) and brine (50 mL). The organic layer was dried with MgSO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography on silica (cHex/EtOAc, 2:1).

83-87-4 (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 10293747, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Johannes, Manuel; Reindl, Maximilian; Gerlitzki, Bastian; Schmitt, Edgar; Hoffmann-Roeder, Anja; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 155 – 161;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

83-87-4, (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of peracetylated or perbenzoylated sugars (300 mg) in 4 mL ofdry DCM at room temperature, TMSN3 (3 equiv) was added followed by the addition of AuBr3 (amounts of the catalyst are given in Table 1 and Table 2). The reaction mixture was stirred either at room temperature or heated to 55-60 C as mentioned in the Table 1 and Table 2. Then, the reaction was quenched byadding triethylamine (20 muL). The mixture was concentrated in vacuo and the crude product was purified by column chromatography.Alternatively, the reaction can be quenched by adding sodium bicarbonate solution followed by extraction with DCM(2 ¡Á 20 mL). The combined organic layers were washed with water, brine and dried over Na2SO4 and concentrated to dryness. The residue was purified by column chromatography on silica gel using petroleum ether (bp 60-70 C) and EtOAc., 83-87-4

83-87-4 (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 10293747, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Rajput, Jayashree; Hotha, Srinivas; Vangala, Madhuri; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 682 – 687;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

83-87-4,83-87-4, (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1,2,3,4,6-penta-O-acetyl-D-glucopyranose (1.678g, 4.30mmol) dissolved in DCM (10.75mL) was added hydrogen bromide (33% in acetic acid, 2.97mL) dropwise at 0C. The reaction mixture was then allowed to warm to room temperature and stir for an additional 4h. The reaction was quenched with water and the aqueous layer was extracted with DCM. The organic layers were combined and washed with water, saturated aqueous NaHCO3, brine, and then dried with sodium sulfate and concentrated under reduced pressure to afford a clear viscous oil that was immediately added to a biphasic mixture of diphyllin (1.090g, 2.87mmol) and TBAB (0.933g, 2.89mmol) in CHCl3 (100mL) and aqueous NaOH (0.1M, 100mL) at 40C. The mixture was maintained at 40C overnight. After cooling to room temperature, the layers were separated and the aqueous layer was extracted three times with CHCl3. The combined organic layers were washed with brine, dried with sodium sulfate, and concentrated under reduced pressure. Flash chromatography (silica gel, 0.3%?1% MeOH in CHCl3) afforded compound 8a (1.928g, 95%) as a white solid:

83-87-4 (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 10293747, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Woodard, John L.; Huntsman, Andrew C.; Patel, Pratiq A.; Chai, Hee-Byung; Kanagasabai, Ragu; Karmahapatra, Soumendrakrishna; Young, Alexandria N.; Ren, Yulin; Cole, Malcolm S.; Herrera, Denisse; Yalowich, Jack C.; Kinghorn, A. Douglas; Burdette, Joanna E.; Fuchs, James R.; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2354 – 2364;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.83-87-4,(3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate,as a common compound, the synthetic route is as follows.

83-87-4, 1,2,3,4,6-tetraacetylglucose (5.5 g, 7.1 mmoles) and hydrazine acetate (0.8 g, 1.2 eq) were dissolved in 20 mL of DMF. After 1 hour, DMF was removed under reduced pressure, the crude product was dissolved in 50 mL of ethyl acetate and washed twice with 20 mL of water. The organic layer was dried over sodium sulfate. 2 g of product was obtained after chromatography (cyclohexane/AcOEt 6/4) (yield: 65%). The characterization data were consistent with the chemical structure.

The synthetic route of 83-87-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Grinstaff, Mark W.; Barthelemy, Philippe; Prata, Carla; Moreau, Louis; US2006/241071; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

83-87-4, (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,83-87-4

In a 50 mL round bottom flask, add compound 1a (2.0 g, 5.13 mmol). Dissolve it in anhydrous dichloromethane (5 mL), subsequently, a 33% hydrobromic acid in acetic acid solution (2.5 mL) was slowly added dropwise, and reacted at room temperature for 2 h. After the reaction, the reaction solution was poured into a separatory funnel and 100 mL of dichloromethane was added. The organic phase was washed with water. After extraction, the organic phase was washed with an aqueous sodium hydrogen carbonate solution. Until no bubbles are generated, and finally washed with saturated brine, the organic phase was dried over anhydrous sodium sulfate. After removing the sodium sulfate solid by filtration, the solvent was distilled off under reduced pressure, The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 4: 1),1b (1.81 g) was obtained as a white flaky solid.Yield: 85.4%

As the paragraph descriping shows that 83-87-4 is playing an increasingly important role.

Reference£º
Patent; Longkou Joint Chemical Co., Ltd.; Li Xiumei; Gao Qingzhi; Ji Wei; Wang He; Wang Jian; (32 pag.)CN107602649; (2019); B;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics