METHYL 4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE

The systematic name of this chemical is Methyl 4,6-O-benzylidene-alpha-D-glucopyranoside. With the CAS registry number 3162-96-7 and EINECS registry number 221-615-2, it is also called a-D-Glucopyranoside, methyl4,6-O-(phenylmethylene)-. In addition, the molecular formula is C₁₄H₁₈O₆ and the molecular weight is 282.29. It is a kind of white crystalline solid and belongs to the classes of Sugars, Carbohydrates & Glucosides; 13C & 2H Sugars; Biochemistry; Glucose; Glycosides; O-Substituted Sugars; Sugars; Carbohydrates & Derivatives.

Physical properties about this chemical are: (1)ACD/LogP: 0.89; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.89; (4)ACD/LogD (pH 7.4): 0.89; (5)ACD/BCF (pH 5.5): 2.79; (6)ACD/BCF (pH 7.4): 2.79; (7)ACD/KOC (pH 5.5): 72.52; (8)ACD/KOC (pH 7.4): 72.51; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 55.38 Å²; (13)Index of Refraction: 1.586; (14)Molar Refractivity: 69.61 cm³; (15)Molar Volume: 207.3 cm³; (16)Polarizability: 27.59 ×10^-24cm³; (17)Surface Tension: 56.4 dyne/cm; (18)Density: 1.36 g/cm³; (19)Flash Point: 239.8 °C; (20)Enthalpy of Vaporization: 77.54 kJ/mol; (21)Boiling Point: 473 °C at 760 mmHg; (22)Vapour Pressure: 9.45E-10 mmHg at 25°C.

Preparation of Methyl 4,6-O-benzylidene-alpha-D-glucopyranoside: it can be prepared by methyl a-D-mannopyranoside and dimethoxymethyl-benzene. The other two products are methyl-[O2,O3;O4,O6-((S,R)-dibenzylidene)-a-D-mannopyranoside] and methyl-[O2,O3;O4,O6-((R,R)-dib. This reaction will need reagent pyridinium p-toluenesulfonate and solvent dimethylformamide. The reaction time is 2 hours at reaction temperature of 80 °C. The yield is about 51%.

Uses of Methyl 4,6-O-benzylidene-alpha-D-glucopyranoside: it can react with N-dichloromethylene-N,N-diethylammonium chloride to get methyl 4,6-O-benzylidene-2-O-(N,N-diethylcarbamoyl)-a-D-mannoside. This reaction will need reagent triethylamine and solvent CH₂Cl₂. The reaction time is 5 hours at reaction temperature of 25 °C by. The yield is about 90%.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It can cause burns. During using it, wear suitable protective clothing, gloves and eye/face protection and avoid contact with skin and eyes. And you should not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). What's more, you should take off all contaminated clothing immediately.

You can still convert the following datas into molecular structure:
(1)SMILES: O1C[C@H]3O[C@H](OC)[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1c2ccccc2
(2)InChI: InChI=1/C14H18O6/c1-17-14-11(16)10(15)12-9(19-14)7-18-13(20-12)8-5-3-2-4-6-8/h2-6,9-16H,7H2,1H3/t9-,10-,11-,12-,13-,14+/m1/s1
(3)InChIKey: VVSWDMJYIDBTMV-UQPQVDFHBV