Description

5-Azido-6-(tert-Butyldimethylsilyl)-2,3-o-Isopropylidene L-Gulono-1,4-Lactone is a sophisticated, multi-functional chiral building block and key synthetic intermediate. This compound is valued for its unique azido and protected hydroxyl functionalities, enabling precise stereochemical control in complex organic syntheses. It is primarily utilized by research chemists and process development scientists in the pharmaceutical and fine chemical industries for the synthesis of novel nucleoside analogs, carbohydrate-based therapeutics, and other high-value specialty molecules.

Application

• Pharmaceutical Intermediate: A critical precursor in the synthesis of novel nucleoside and nucleotide analogs with potential antiviral or anticancer activity.
• Carbohydrate Chemistry: Used in the stereoselective construction of complex sugar derivatives, glycoconjugates, and glycomimetics for drug discovery.
• Click Chemistry Substrate: The azido group makes it an ideal partner for copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, facilitating bioconjugation and polymer functionalization.
• Protecting Group Strategy: The tert-butyldimethylsilyl (TBDMS) and isopropylidene groups allow for selective deprotection sequences in multi-step synthetic routes.
• Chemical Biology Probe Development: Serves as a starting material for creating labeled or tagged carbohydrate probes to study biological recognition processes.
• Process Chemistry & Scale-up: Employed in the development and optimization of scalable routes to active pharmaceutical ingredients (APIs) requiring specific sugar moieties.

Basic Information

Product Name	5-Azido-6-(tert-Butyldimethylsilyl)-2,3-o-Isopropylidene L-Gulono-1,4-Lactone
CAS No.	118464-49-6
Molecular Formula	C15H27N3O5Si
Molecular Weight	357.48 g/mol
Synonyms	5-Azido-6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-L-gulono-1,4-lactone; 1,4-Lactone, 5-azido-6-O-[(1,1-dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-L-gulono-; 5-Azido-6-O-TBDMS-2,3-O-isopropylidene-L-gulono-1,4-lactone; 2,3-O-Isopropylidene-5-azido-6-O-tert-butyldimethylsilyl-L-gulono-1,4-lactone; L-Gulono-1,4-lactone, 5-azido-6-O-[(1,1-dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-; 5-Azido-6-TBDMS-2,3-O-isopropylidene-L-gulono-1,4-lactone; Azido-TBDMS-isopropylidene gulonolactone
EINECS	Contact for details

Quality Control

Our production of 5-Azido-6-(tert-Butyldimethylsilyl)-2,3-o-Isopropylidene L-Gulono-1,4-Lactone adheres to stringent quality protocols suitable for research and development applications. Each batch is characterized and tested to ensure identity, purity, and consistency. Certificates of Analysis (COA) detailing key parameters such as assay (HPLC), chiral purity, and impurity profile are provided with every shipment. We support cGMP-compliant production for advanced pharmaceutical applications upon request.

Storage

Preserve in a tightly closed container, protected from light. Store at 2-8°C (refrigerated) or as indicated on the label or COA. For long-term storage under an inert atmosphere, consider storing sealed containers at -20°C. The compound is light-sensitive; handling should be performed under subdued light where practical.

Specification

Item	Specification
Appearance	White to off-white solid
Identification (IR)	Conforms to structure
Identification (NMR)	Conforms to structure
Assay (HPLC)	≥ 95.0%
Chiral Purity	≥ 98.0% ee
Water Content (KF)	≤ 1.0%
Residual Solvents (GC)	Meets ICH guidelines

Note: Specifications can be tailored. Please contact us for the detailed technical data sheet of a specific grade.