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

• ChemBase ID: 132993
• Molecular Formular: C12H16O7
• Molecular Mass: 272.25124
• Monoisotopic Mass: 272.08960285
• SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H](C=CO1)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@H]1OC=C[C@H]([C@@H]1OC(=O)C)OC(=O)C
• InChI: InChI=1S/C12H16O7/c1-7(13)17-6-11-12(19-9(3)15)10(4-5-16-11)18-8(2)14/h4-5,10-12H,6H2,1-3H3/t10-,11-,12+/m1/s1
• InChIKey: LLPWGHLVUPBSLP-UTUOFQBUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R)-3,4-bis(acetyloxy)-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R)-3,4-bis(acetyloxy)-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• Synonyms: (2R,3S,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate; 1,2-Dideoxy-3,4,6-tri-O-acetyl-D-arabino-1-hexenopyranose; 3,4,6-Tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol; Tri-O-acetyl-D-glucal; 3,4,6-Tri-O-acetyl-D-glucal; 3,4,6-O-三乙酰基-D-葡萄糖烯; 三-O-乙酰基-D-葡萄烯糖; 三乙酰葡萄烯糖; 3,4,6-O-三乙酰基-D-葡萄烯糖

Database IDs

• CAS Number: 2873-29-2
• EC Number: 220-709-0
• MDL Number: MFCD00063253
• Beilstein Number: 90781
• PubChem SID: 162227270; 24900208
• PubChem CID: 688303

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.31396386
• LogD (pH = 7.4): -0.31396386
• Log P: -0.31396386
• Molar Refractivity: 61.2336 cm^3
• Polarizability: 25.050026 Å^3
• Polar Surface Area: 88.13 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 52-55°C; 53-55 °C(lit.)
• Flash Point: >113 °C; >235.4 °F
• Optical Rotation: [α]20/D -24.0±2.0°, c = 1% in chloroform; [α]25/D -12°, c = 2 in ethanol; -25 (c=1 in methanol)

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (HPLC); 95+%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C12H16O7

DETAILS

Sigma Aldrich - T44407

Application
Important building block for both solution- and solid-phase synthesis of oligosaccharides.1
Packaging
25, 100 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 90260

Other Notes
Chiral building block, important intermediate for the preparation of various sugars 1,2,3; Preparation of C-glycosides 4