L-Xylopyranose, 5-C-[4-chloro-3-[(4-ethoxyphenyl)Methyl]phenyl]-, 1,2,3,4-tetraacetate,(5S)-

China [CN]

Core Applications: 1. Pharmaceutical intermediates: Used in the synthesis of C-aryl glycoside drugs (such as SGLT2 inhibitors, anti-inflammatory drugs), and antiviral drugs (such as nucleoside prodrugs); 2. Fine chemicals: As a chiral carbohydrate synthesis building block, used in the total synthesis of complex natural products and chiral drugs.

Key Structural Features: 1. Contains an L-xylopyranose chiral core + (5S) chiral center, with a non-natural L-configuration, offering a high degree of customization; 2. The 5-position is C-arylated (C-C bond connection), which is more resistant to enzymatic hydrolysis than O-glycosidic bonds, improving drug stability in vivo; 3. Four hydroxyl groups are fully protected by acetyl groups, resulting in a single reaction site (only the aryl side chain can be modified); 4. The aryl group contains a chlorine atom and an ethoxybenzyl group, which can adjust molecular lipophilicity and target binding affinity.

Key Physicochemical Properties (Inferred): 1. Appearance: White to off-white crystalline powder (typical morphology of carbohydrate ester derivatives, crystallinity improves with higher purity); 2. Solubility: Slightly soluble in water, readily soluble in dichloromethane, ethyl acetate, acetone, tetrahydrofuran, soluble in methanol/ethanol, sparingly soluble in petroleum ether (tetraacetate + aryl group, significantly lipophilic); 3. Stability: Stable under normal temperature, sealed, and light-protected storage; avoid strong acids (acetyl group deprotection), strong bases (aryl side chain hydrolysis), and high temperatures (≥100℃ easily causes deacetylation); 4. Melting point: Expected 140-160℃ (pyranose ring + tetraacetate + aryl group, moderate melting point).

Key Quality Indicators (Suggested): 1. Chiral purity (ee value): ≥99% ((5S) configuration + L-xylose core, a core indicator affecting the optical activity of downstream drugs); 2. Chemical purity (HPLC): ≥98.5%; 3. Moisture content: ≤0.5% (carbohydrate derivatives are prone to moisture absorption, strict moisture control is required); 4. 5. Acetyl protection rate: ≥99% (to avoid mono-/di-deacetylation impurities); 5. Isomer impurities: α/β-pyranose isomers ≤0.5% (xylopyranose rings are prone to conformational isomerism).