Product Description
(3R,3AS,6AR)-羟基六氢呋喃并[2,3-Β]呋喃基丁二酰亚胺基碳酸酯化学性质熔点:122-125℃沸点:391.8±52.0°C(Predicted)密度:1.51蒸Chemicalbook气压:0-0Paat20-25℃储存条件:2-8°C溶解度:Chloroform(Slightly),EthylAcetate(Slightly)形态:Solid颜色:White
AI Product Description
*The following content is generated by AI and is for reference only.
The compound designated as [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate] is a specialized chiral reagent widely utilized in advanced organic synthesis and medicinal chemistry. Its molecular formula is C13H15NO7, reflecting a complex structure that integrates a specific stereochemically defined hexahydrofuro[2,3-b]furan core with a reactive succinimidyl carbonate moiety. While a unique CAS registry number for this exact stereoisomer may vary depending on specific vendor cataloging conventions, it is structurally derived from the enantiopure diol precursor (3R,3aS,6aR)-hydroxyhexahydrofuro[2,3-b]furan. This molecule serves primarily as an activated carbonate ester, designed to facilitate efficient carbamate formation under mild conditions.
The primary utility of this reagent lies in its ability to act as a coupling agent for introducing carbamate protecting groups or forming amide linkages with high regioselectivity and stereochemical fidelity. In pharmaceutical research, preserving the integrity of chiral centers during derivatization is critical; this compound excels in such applications by reacting selectively with primary amines to yield stable N-substituted carbamates without racemizing sensitive adjacent stereocenters. The succinimidyl leaving group ensures a favorable reaction kinetics profile, allowing transformations to proceed efficiently at ambient temperatures in standard organic solvents like dichloromethane or acetonitrile. Consequently, it is frequently employed in the solid-phase synthesis of peptides, the modification of oligonucleotides, and the construction of complex heterocyclic scaffolds found in bioactive natural products.
Beyond peptide chemistry, this reagent finds application in the development of prodrugs and targeted delivery systems where controlled release mechanisms rely on carbamate stability. The specific (3R,3aS,6aR) configuration imparts distinct three-dimensional geometry, making it indispensable for synthesizing molecules requiring precise spatial orientation for biological receptor binding. Researchers value this material for its reliability in generating high-purity intermediates essential for drug discovery pipelines. By minimizing side reactions and maximizing yield, it streamlines synthetic routes for complex therapeutic agents. Overall, [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate] represents a vital tool for chemists seeking to manipulate nitrogen-containing functional groups within intricate chiral frameworks, bridging the gap between fundamental organic methodology and practical pharmaceutical manufacturing.
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