IdentificationPhysical DataSpectraRoute of Synthesis (ROS)Safety and HazardsOther Data
Identification
Product Name1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranoseIUPAC Name(3,4,5,6-tetrabenzoyloxyoxan-2-yl)methyl benzoateMolecular StructureCAS Registry Number 41569-33-9EINECS NumberNo data availableMDL NumberNo data availableBeilstein Registry NumberNo data availableSynonyms1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside, 1,2,3,4,6-penta-O-benzoyl α-D-glucopyranoside, 1,2,3,4,6-penta-O-benzyl-β-D-glucopyranoside, benzoyl 2,3,4,6-tetra-O-benzoyl-D-glucopyranoside, 1,2,3,4,6-penta-O-benzoyl-D-glucopyranose, penta-O-benzoyl-D-glucopyranose, per-O-benzoylated glucopyranoseMolecular FormulaC41H32O11Molecular Weight700.69InChIInChI=1S/C41H32O11/c42-36(27-16-6-1-7-17-27)47-26-32-33(49-37(43)28-18-8-2-9-19-28)34(50-38(44)29-20-10-3-11-21-29)35(51-39(45)30-22-12-4-13-23-30)41(48-32)52-40(46)31-24-14-5-15-25-31/h1-25,32-35,41H,26H2InChI KeyJJNMLNFZFGSWQR-UHFFFAOYSA-NCanonical SMILESC1=CC=C(C=C1)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6
Patent InformationPatent IDTitlePublication DateUS2016/264609DISACCHARIDE INTERMEDIATE AND SYNTHESIS METHOD THEREOF2016
Physical Data
AppearanceWhite to off-white powderSolubilityNo data availableFlash PointNo data availableRefractive indexNo data availableSensitivityNo data available
Melting Point, °C 172 - 174
Spectra
Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHzChemical shifts, Spectrum1Hchloroform-d1599.9Chemical shifts, Spectrum13Cchloroform-d1150.81Hchloroform-d1Chemical shifts1HCDCl3300Chemical shifts13CCDCl375
1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranose CAS#: 41569-33-9 HNMR
Description (Mass Spectrometry)Comment (Mass Spectrometry)PeakESI (Electrospray ionisation), HRMS (High resolution mass spectrometry)Molecular peak 723.1818 m/z
Route of Synthesis (ROS)
Route of Synthesis (ROS) of 1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranose CAS 41569-33-9
ConditionsYieldWith hydrogen bromide; acetic acid In dichloromethane at 0 - 20℃; for 2h;Experimental ProcedureStep (b) To a solution of 1,2,3,4,6-penta-O-benzoyl-D-glucopyranose (2.5 g, 3.57 mmol) in anhydrous CH2C12 at 0 °C was added HBr solution in AcOH (33%, 10 mL) and stirred for 1 hr. The temperature was then increased to room temperature and stirred for another hour. The solvent was removed under vacuum and the residue was dissolved in CH2C12 (100 mL) and neutralized with saturated aqueous NaHC03 (50 mL). The organic layer was separated and washed with H20 (3 x 50 mL), saturated aqueous NaHC03 (3 x 30 mL) and brine (2 x 30 mL). Then the solution was dried with anhydrous Na2S04, filtered and concentrated in vacuum to afford 2,3,4,6-tetra-O-benzoyl-a-D-glucopyranosyl bromide quantitatively as a white foamy solid100%With hydrogen bromide In acetic anhydride; acetic acid at 50℃; for 4.5h;97%With hydrogenchloride; hydrogen bromide In 1,2-dichloro-ethane at 20℃; for 2h; Cooling with ice;Experimental ProcedureReagents and reaction conditions: benzoyl chloride, pyridine, room temperature; () 33% hydrobromic acid in acetic acid, 1,2-dichloroethane, room temperature.Preparation steps: (i) taking D- glucose (. 15g, 83 26mmol) in the reaction flask was added 150mL of anhydrous pyridine, stirred at rt for 30min, was added dropwise benzoyl chloride (60mL, 520.7mmol) under ice-water bath cooled sufficiently. Completion of the dropwise addition, stirring at room temperature for 15min, then the reaction was continued at 60 ° C 2h. The reaction solution was poured into ice water, stand until after curing, and the filter cake was washed successively with dilute hydrochloric acid, water, and methanol, and dried to obtain a white powder sample S-1 (53. 47g, yield 91.7%) . (ii) to take S-l (20g, 28. 54mmol) in the reaction flask was added lOOmLl, 2- dichloroethane was added dropwise 33% hydrobromic acid / acetic acid solution (80mL, 463. 3mmol) under an ice-water bath cooled sufficiently. Completion of the dropwise addition, then stirred at room temperature for 2h. The reaction solution was poured into a mixture of ethyl acetate and ice water, extracted organic phase was washed successively with saturated aqueous sodium bicarbonate and water, dried over anhydrous magnesium sulfate, and ethyl acetate recovered under reduced pressure, the resulting residue was 300mL cyclohexane dispersion, ultrasound, a solid, the filter cake dried to obtain a white powder of 2,3,4,6-tetrabenzoyl-(1-bromo-glucopyranose (S-02) 17.48 g, yield 92%.92%
Safety and Hazards
No data available
Other Data
TransportationNONH for all modes of transportUnder the room temperature and away from lightHS CodeNo data availabeStorageUnder the room temperature and away from lightShelf Life2 yearsMarket PriceUSD
DruglikenessLipinski rules componentMolecular Weight700.698logP8.872HBA11HBD0Matching Lipinski Rules1Veber rules componentPolar Surface Area (PSA)140.73Rotatable Bond (RotB)16Matching Veber Rules0
Use Pattern1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranose CAS#: 41569-33-9 used as pharmaceutical intermediates.
https://www.chemwhat.com/12346-penta-o-benzoyl-alpha-d-mannopyranose-cas-41569-33-9/
Identification
Product Name1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranoseIUPAC Name(3,4,5,6-tetrabenzoyloxyoxan-2-yl)methyl benzoateMolecular StructureCAS Registry Number 41569-33-9EINECS NumberNo data availableMDL NumberNo data availableBeilstein Registry NumberNo data availableSynonyms1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside, 1,2,3,4,6-penta-O-benzoyl α-D-glucopyranoside, 1,2,3,4,6-penta-O-benzyl-β-D-glucopyranoside, benzoyl 2,3,4,6-tetra-O-benzoyl-D-glucopyranoside, 1,2,3,4,6-penta-O-benzoyl-D-glucopyranose, penta-O-benzoyl-D-glucopyranose, per-O-benzoylated glucopyranoseMolecular FormulaC41H32O11Molecular Weight700.69InChIInChI=1S/C41H32O11/c42-36(27-16-6-1-7-17-27)47-26-32-33(49-37(43)28-18-8-2-9-19-28)34(50-38(44)29-20-10-3-11-21-29)35(51-39(45)30-22-12-4-13-23-30)41(48-32)52-40(46)31-24-14-5-15-25-31/h1-25,32-35,41H,26H2InChI KeyJJNMLNFZFGSWQR-UHFFFAOYSA-NCanonical SMILESC1=CC=C(C=C1)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6
Patent InformationPatent IDTitlePublication DateUS2016/264609DISACCHARIDE INTERMEDIATE AND SYNTHESIS METHOD THEREOF2016
Physical Data
AppearanceWhite to off-white powderSolubilityNo data availableFlash PointNo data availableRefractive indexNo data availableSensitivityNo data available
Melting Point, °C 172 - 174
Spectra
Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHzChemical shifts, Spectrum1Hchloroform-d1599.9Chemical shifts, Spectrum13Cchloroform-d1150.81Hchloroform-d1Chemical shifts1HCDCl3300Chemical shifts13CCDCl375
1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranose CAS#: 41569-33-9 HNMR
Description (Mass Spectrometry)Comment (Mass Spectrometry)PeakESI (Electrospray ionisation), HRMS (High resolution mass spectrometry)Molecular peak 723.1818 m/z
Route of Synthesis (ROS)
Route of Synthesis (ROS) of 1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranose CAS 41569-33-9
ConditionsYieldWith hydrogen bromide; acetic acid In dichloromethane at 0 - 20℃; for 2h;Experimental ProcedureStep (b) To a solution of 1,2,3,4,6-penta-O-benzoyl-D-glucopyranose (2.5 g, 3.57 mmol) in anhydrous CH2C12 at 0 °C was added HBr solution in AcOH (33%, 10 mL) and stirred for 1 hr. The temperature was then increased to room temperature and stirred for another hour. The solvent was removed under vacuum and the residue was dissolved in CH2C12 (100 mL) and neutralized with saturated aqueous NaHC03 (50 mL). The organic layer was separated and washed with H20 (3 x 50 mL), saturated aqueous NaHC03 (3 x 30 mL) and brine (2 x 30 mL). Then the solution was dried with anhydrous Na2S04, filtered and concentrated in vacuum to afford 2,3,4,6-tetra-O-benzoyl-a-D-glucopyranosyl bromide quantitatively as a white foamy solid100%With hydrogen bromide In acetic anhydride; acetic acid at 50℃; for 4.5h;97%With hydrogenchloride; hydrogen bromide In 1,2-dichloro-ethane at 20℃; for 2h; Cooling with ice;Experimental ProcedureReagents and reaction conditions: benzoyl chloride, pyridine, room temperature; () 33% hydrobromic acid in acetic acid, 1,2-dichloroethane, room temperature.Preparation steps: (i) taking D- glucose (. 15g, 83 26mmol) in the reaction flask was added 150mL of anhydrous pyridine, stirred at rt for 30min, was added dropwise benzoyl chloride (60mL, 520.7mmol) under ice-water bath cooled sufficiently. Completion of the dropwise addition, stirring at room temperature for 15min, then the reaction was continued at 60 ° C 2h. The reaction solution was poured into ice water, stand until after curing, and the filter cake was washed successively with dilute hydrochloric acid, water, and methanol, and dried to obtain a white powder sample S-1 (53. 47g, yield 91.7%) . (ii) to take S-l (20g, 28. 54mmol) in the reaction flask was added lOOmLl, 2- dichloroethane was added dropwise 33% hydrobromic acid / acetic acid solution (80mL, 463. 3mmol) under an ice-water bath cooled sufficiently. Completion of the dropwise addition, then stirred at room temperature for 2h. The reaction solution was poured into a mixture of ethyl acetate and ice water, extracted organic phase was washed successively with saturated aqueous sodium bicarbonate and water, dried over anhydrous magnesium sulfate, and ethyl acetate recovered under reduced pressure, the resulting residue was 300mL cyclohexane dispersion, ultrasound, a solid, the filter cake dried to obtain a white powder of 2,3,4,6-tetrabenzoyl-(1-bromo-glucopyranose (S-02) 17.48 g, yield 92%.92%
Safety and Hazards
No data available
Other Data
TransportationNONH for all modes of transportUnder the room temperature and away from lightHS CodeNo data availabeStorageUnder the room temperature and away from lightShelf Life2 yearsMarket PriceUSD
DruglikenessLipinski rules componentMolecular Weight700.698logP8.872HBA11HBD0Matching Lipinski Rules1Veber rules componentPolar Surface Area (PSA)140.73Rotatable Bond (RotB)16Matching Veber Rules0
Use Pattern1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranose CAS#: 41569-33-9 used as pharmaceutical intermediates.
https://www.chemwhat.com/12346-penta-o-benzoyl-alpha-d-mannopyranose-cas-41569-33-9/
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