2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl trichloroacetimidate

2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl trichloroacetimidate

2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl trichloroacetimidate (CAS No: 74808-10-9) is a specialized, highly functionalized glycosyl donor commonly used in carbohydrate and glycoside synthesis.chemsrc+2

Chemical Identity and Composition

• IUPAC Name: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetatelgcstandards

• Molecular Formula: C₁₆H₂₀Cl₃NO₁₀chemicalbook+2

• Molecular Weight: 492.69 g/molchemsrc+2

• SMILES: CC(=O)OC[C@H]1OC@HC@HC@@H[C@@H]1OC(=O)Clgcstandards

Physical and Chemical Properties

• Appearance: Colourless to light yellow; oily liquid to sticky solid.georganics+1

• Melting Point: 66-68 °C (solid form)chemicalbook

• Boiling Point: 463.3 ± 55.0 °C (predicted)chemicalbook

• Density: 1.55 ± 0.1 g/cm³ (predicted)chemicalbook

• Solubility: Slightly soluble in chloroform, dichloromethane, DMSO, and ethyl acetate.chemicalbook

• Stability: Hygroscopic, moisture sensitive; stable under inert, dry conditions, ideally stored at -20°C.bldpharm+2

Uses and Applications

• Role: This compound is a key glycosylation reagent, used extensively in the synthesis of natural glycosides and oligosaccharides.lgcstandards

• Reactivity: The trichloroacetimidate group provides robust donor capability for the stereoselective formation of glycosidic bonds under mild acidic conditions, aiding the construction of complex sugar molecules.lgcstandards+1

• Synthetic Example: It can be activated (e.g., with trimethylsilyl trifluoromethanesulfonate) for coupling reactions, yielding glycosides in high purity.ambeed

Safety and Handling

• Precautions: Avoid moisture and exposure to air; handle under inert atmosphere.georganics+2

• Personal Protection: Use protective gloves, chemical safety glasses, and work in a suitable fume hood.georganics

• Hazard Classification: Often labeled with warnings for skin/eye irritation and respiratory effects; follow recommended hazard and precautionary statements.ambeed+1

Structural and Molecular Information

• Stereochemistry: Retains the D-glucose configuration, fully acetylated at the 2, 3, 4, 6 positions with a trichloroacetimidate moiety at C1.chemsrc+1

• InChI: InChI=1S/C16H20Cl3NO10/c1-6(21)25-5-10-11(26-7(2)22)12(27-8(3)23)13(28-9(4)24)14(29-10)30-15(20)16(17,18)19/h10-14,20H,5H2,1-4H3/t10-,11-,12+,13-,14-/m1/s1.lgcstandards

This compound is invaluable in carbohydrate chemistry for its stereoselective activation and robust role in building natural and synthetic glycosides.ambeed+3