(4aR,6S,7R,8R,8aS)-6-methoxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diol

• ChemBase ID: 145791
• Molecular Formular: C14H18O6
• Molecular Mass: 282.28912
• Monoisotopic Mass: 282.1103383
• SMILES: CO[C@@H]1[C@@H]([C@H]([C@H]2[C@H](O1)COC(O2)c1ccccc1)O)O
• Canonical SMILES: CO[C@H]1O[C@@H]2COC(O[C@H]2[C@@H]([C@H]1O)O)c1ccccc1
• InChI: InChI=1S/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
• InChIKey: VVSWDMJYIDBTMV-BTZLDLHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6S,7R,8R,8aS)-6-methoxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diol
• IUPAC Traditional name: (4aR,6S,7R,8R,8aS)-6-methoxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diol
• Synonyms: 4,6-O-Benzylidene-methyl-α-D-glucopyranoside; Methyl 4,6-O-benzylidene-α-D-glucopyranoside; (+)-(4,6-O-Benzylidene)methyl-α-D-glucopyranoside; (4aR,6S,7R,8R,8aS)-6-Methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol; Methyl-4,6-O-benzylidene-α-D-glucopyranoside; 4,6-O-亚苄基-甲基-α-D-吡喃葡萄糖苷; 甲基 4,6-O-亚苄基-α-D-吡喃葡萄糖苷; (+)-(4,6-O-亚苄基)甲基-α-D-吡喃葡萄糖苷; 4,6-O-苯亚甲基-α-D-葡萄糖苷; 甲基-4,6-O-亚苄基-α-D-吡喃葡萄糖苷

Database IDs

• CAS Number: 3162-96-7
• EC Number: 221-615-2
• MDL Number: MFCD00006819
• Beilstein Number: 89619
• PubChem SID: 162239993; 24857614
• PubChem CID: 11822086

CALCULATED PROPERTIES

• Acid pKa: 12.276533
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.87566644
• LogD (pH = 7.4): 0.8756608
• Log P: 0.87566656
• Molar Refractivity: 67.5582 cm^3
• Polarizability: 27.693336 Å^3
• Polar Surface Area: 77.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 164-165 °C(lit.); 164-167 °C
• Optical Rotation: [α]19/D +113.1°, c = 1 in chloroform; [α]20/D +110±3°, c = 2% in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (sum of enantiomers, HPLC); 95+%; 97%
• Grade: purum
• Empirical Formula (Hill Notation): C14H18O6
• Classification: Rare Derivatives of Natural Compounds

DETAILS

Sigma Aldrich - 292842

Application
Chiral building block. Important intermediate in the preparation of various sugars.
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 65895

Other Notes
Chiral building block, important intermediate in the preparation of different sugars1,2,3,4,5