(2R,3S,4R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-3,4-dihydro-2H-pyran

• ChemBase ID: 150893
• Molecular Formular: C27H28O4
• Molecular Mass: 416.50882
• Monoisotopic Mass: 416.19875938
• SMILES: c1ccc(cc1)COC[C@@H]1[C@H]([C@@H](C=CO1)OCc1ccccc1)OCc1ccccc1
• Canonical SMILES: c1ccc(cc1)CO[C@@H]1[C@@H](COCc2ccccc2)OC=C[C@H]1OCc1ccccc1
• InChI: InChI=1S/C27H28O4/c1-4-10-22(11-5-1)18-28-21-26-27(31-20-24-14-8-3-9-15-24)25(16-17-29-26)30-19-23-12-6-2-7-13-23/h1-17,25-27H,18-21H2/t25-,26-,27+/m1/s1
• InChIKey: MXYLLYBWXIUMIT-PFBJBMPXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-3,4-dihydro-2H-pyran
• IUPAC Traditional name: (2R,3S,4R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-3,4-dihydro-2H-pyran
• Synonyms: Tri-O-benzyl-D-glucal; 3,4,6-Tri-O-benzyl-D-glucal; 三苄基-D-葡萄糖烯

Database IDs

• CAS Number: 55628-54-1
• MDL Number: MFCD00061640
• Beilstein Number: 1691968
• PubChem SID: 162245053; 24860481; 24889394
• PubChem CID: 11742644

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 5.465459
• LogD (pH = 7.4): 5.465459
• Log P: 5.465459
• Molar Refractivity: 121.8705 cm^3
• Polarizability: 47.89774 Å^3
• Polar Surface Area: 36.92 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 57-58 °C(lit.); 57-58°C; 57-59 °C
• Optical Rotation: [α]20/D -2.7±0.5°, c = 5% in chloroform; [α]25/D -2.7°, c = 5 in chloroform; -2.7 (c=5 in chloroform)

Safety Information

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

Product Information

• Purity: ≥95.0% (sum of enantiomers, TLC); 97%
• Grade: purum
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C27H28O4

DETAILS

Sigma Aldrich - 337439

Application
Important building block for both solution- and solid-phase synthesis of oligosaccharides.1
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 90672

Other Notes
Carbohydrate building block; synthesis of α- and β-glycosides 1,2,3