3,4-Di-O-acetyl-L-rhamnal

3,4-Di-O-acetyl-L-rhamnal, also known as 3,4-di-O-acetyl-6-deoxy-L-glucal, is a chemically synthesized carbohydrate derivative widely used as a synthetic intermediate in organic and carbohydrate chemistry. It is derived from L-rhamnose through selective acetylation of hydroxyl groups at positions 3 and 4, forming a diacetylated glycal structure characterized by a double bond in the sugar ring. This compound serves as an important precursor in the synthesis of biologically active natural products, oligosaccharides, and polysaccharides. The utility of 3,4-Di-O-acetyl-L-rhamnal extends to glycosyl donor applications, enabling the stereoselective construction of O-glycosides, C-glycosides, S-glycosides, and N-glycosides, which are important for medicinal chemistry and glycobiology research. Its stable, high-purity form and well-defined properties make it valuable for laboratories involved in carbohydrate synthesis and drug discovery.

IUPAC Name

• [(2S,3R,4R)-3-acetyloxy-2-methyl-3,4-dihydro-2H-pyran-4-yl] acetate
• Also known as 3,4-Di-O-acetyl-6-deoxy-L-glucal or Di-O-acetyl-L-rhamnal

Appearance

• Colorless to pale yellow viscous liquid
• Can also be supplied as a liquid with characteristic optical activity and refractive index

Source

• Synthesized chemically from L-rhamnose derivatives through acetylation and elimination reactions

Molecular Weight and Structure

• Molecular formula: C10H14O5
• Molecular weight: 214.22 g/mol
• Structure: Glycal ring (unsaturated pyranose) with acetyl groups at positions 3 and 4, methyl substitution at position 2
• SMILES: C[C@H]1C@@HOC(=O)C

Sugar Specificity

• Derived specifically from L-rhamnose, representing a 6-deoxy sugar class
• Acts as a glycal glycosyl donor suitable for regulated glycosylation reactions

Biological Activity

• Primarily a synthetic intermediate with no direct biological effect
• Supports synthesis of bioactive glycosides and carbohydrates with demonstrated biological roles

Purity and Microbial Contamination

• Purity generally >95% verified by NMR and chromatographic analysis
• Due to synthesis origin, microbial contamination is generally negligible and not reported

Identity and Quality Control

• Confirmed by NMR spectroscopy, HPLC, mass spectrometry, and optical rotation
• Batch release supported by Certificates of Analysis and SDS documentation
• Refractive index around 1.454, optical rotation [α]/D ~55° in chloroform
• Boiling point: 68-69 °C at 0.06 mmHg

Shelf Life and Storage

• Recommended storage at 2–8°C, preferably in sealed containers protected from light and moisture
• Shelf life typically 1 year or longer under proper conditions

Application

• Used as a glycosyl donor in synthesis of O-, C-, S-, and N-glycosides
• Employed extensively in carbohydrate chemistry to construct oligosaccharides and complex glycoconjugates
• Facilitates stereoselective glycosylation reactions in medicinal chemistry and drug development
• Intermediate in synthetic routes towards natural products containing rhamnose units
• Supports development of novel glycomimetic compounds and biochemical probes

Key Characteristics

• Glycal derivative with acetyl groups at 3 and 4 positions on L-rhamnal
• CAS number 34819-86-8
• Colorless to pale yellow viscous liquid, molecular weight 214.22 g/mol
• High chemical purity >95% with comprehensive quality control
• Key reagent/synthon for stereoselective glycosylation and carbohydrate synthesis
• Stable under refrigeration for at least one year
• Used for synthesis of bioactive glycosides and polysaccharides
• Verified identity by spectral and chromatographic methods
• Optical activity and refractive index well-characterized
• Important intermediate for medicinal and synthetic carbohydrate chemistry

Citation 

• Sigma-Aldrich product data on 3,4-Di-O-acetyl-L-rhamnal
• Fisher Scientific ACS reagent information
• PubChem chemical description and structure
• TCI Chemicals product specification
• ChemicalBook datasheet
• Research article on synthetic method
• MedChem Express synthesis intermediate
• TargetMol chemical catalog
• Glycon Biochem catalog entry
• ImmunoMart reagent data