1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranose CAS#: 41569-33-9

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data


Product Name1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranose
IUPAC Name(3,4,5,6-tetrabenzoyloxyoxan-2-yl)methyl benzoate
Molecular StructureStructure of 1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranose CAS 41569-33-9
CAS Registry Number 41569-33-9
EINECS NumberNo data available
MDL NumberNo data available
Beilstein Registry NumberNo data available
Synonyms1,2,3,4,6-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 glucopyranose
Molecular FormulaC41H32O11
Molecular Weight700.69
Canonical 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 Information
Patent IDTitlePublication Date

Physical Data

AppearanceWhite to off-white powder
SolubilityNo data available
Flash PointNo data available
Refractive indexNo data available
SensitivityNo data available
Melting Point, °C
172 – 174


Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Chemical shifts, Spectrum1Hchloroform-d1599.9
Chemical shifts, Spectrum13Cchloroform-d1150.8
Chemical shifts1HCDCl3300
Chemical shifts13CCDCl375
1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranose CAS#: 41569-33-9 HNMRHNMR of 1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranose CAS 41569-33-9
Description (Mass Spectrometry)Comment (Mass Spectrometry)Peak
ESI (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
Route of Synthesis (ROS) of 1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranose CAS 41569-33-9
With hydrogen bromide; acetic acid In dichloromethane at 0 – 20℃; for 2h;
Experimental Procedure
Step (b) [00245] 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 solid
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 Procedure
Reagents 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%.

Safety and Hazards

No data available

Other Data

TransportationNONH for all modes of transport
Under the room temperature and away from light
HS CodeNo data availabe
StorageUnder the room temperature and away from light
Shelf Life2 years
Market PriceUSD
Lipinski rules component
Molecular Weight700.698
Matching Lipinski Rules1
Veber rules component
Polar Surface Area (PSA)140.73
Rotatable Bond (RotB)16
Matching Veber Rules0
Use Pattern
1,2,3,4,6-Penta-O-benzoyl-alpha-D-mannopyranose CAS#: 41569-33-9 used as pharmaceutical intermediates.

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