(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-ol

• ChemBase ID: 67493
• Molecular Formular: C34H36O6
• Molecular Mass: 540.64604
• Monoisotopic Mass: 540.25118887
• SMILES: OC1[C@H](OCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H](O1)COCc1ccccc1
• Canonical SMILES: OC1O[C@H](COCc2ccccc2)[C@H]([C@@H]([C@H]1OCc1ccccc1)OCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C34H36O6/c35-34-33(39-24-29-19-11-4-12-20-29)32(38-23-28-17-9-3-10-18-28)31(37-22-27-15-7-2-8-16-27)30(40-34)25-36-21-26-13-5-1-6-14-26/h1-20,30-35H,21-25H2/t30-,31-,32+,33-,34?/m1/s1
• InChIKey: OGOMAWHSXRDAKZ-BKJHVTENSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-ol
• IUPAC Traditional name: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-ol
• Synonyms: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose; 2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose; 2,3,4,6-Tetra-O-benzyl-D-glucopyranose; 2,3,4,6-四-O-苄基-D-吡喃葡萄糖; 2,3,4,6-四-氧苯甲基-D-吡喃葡萄糖

Database IDs

• CAS Number: 4132-28-9
• MDL Number: MFCD00066004
• PubChem SID: 24888761; 162033228; 24899895
• PubChem CID: 10940502

CALCULATED PROPERTIES

• Acid pKa: 11.343017
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 6.5378585
• LogD (pH = 7.4): 6.53781
• Log P: 6.5378594
• Molar Refractivity: 153.3786 cm^3
• Polarizability: 60.869534 Å^3
• Polar Surface Area: 66.38 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: White Solid
• Melting Point: 145-149 °C(lit.); 150-153°C; 150-155°C; 151-156 °C
• Optical Rotation: [α]20/D +49±2°, c = 2% in dioxane

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC); ≥98.0% (TLC); 95+%; 98%; 98+%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C34H36O6

DETAILS

Sigma Aldrich - 86730

Other Notes
Important D-glucopyranose derivative for glucosylations and other reactions 1,2; Preparation of the α-glucopyranosyl chloride 3; Synthesis of 1-C-α-D-glucopyranose derivatives 4
Packaging
1, 5 g in glass bottle