Description
alpha-D-Glucofuranuronic acid, 1,2-O-(1-methylethylidene)-, gamma-lactone (CAS No. 20513-98-8) is a highly specialized carbohydrate derivative with the molecular formula C9H12O6. This compound features a unique fused-ring structure incorporating a glucofuranuronic acid core protected by an isopropylidene group, forming a gamma-lactone. Its intricate stereochemistry and functional groups make it a valuable intermediate in synthetic organic chemistry, particularly in the synthesis of complex sugars, nucleosides, and glycoconjugates. With a purity suitable for research applications, this product is ideal for pharmaceutical development, glycoscience studies, and enzymatic research. Store in a cool, dry place under inert conditions to ensure stability.
Properties
- CAS Number: 20513-98-8
- Complexity: 314
- IUPAC Name: (1S,2R,6R,8R,9S)-9-hydroxy-4,4-dimethyl-3,5,7,11-tetraoxatricyclo[6.3.0.02,6]undecan-10-one
- InChI: InChI=1S/C9H12O6/c1-9(2)14-6-5-4(13-8(6)15-9)3(10)7(11)12-5/h3-6,8,10H,1-2H3/t3-,4+,5-,6+,8+/m0/s1
- InChI Key: BDBGJSXZKMTMGP-UXTLFEIASA-N
- Exact Mass: 216.06338810
- Molecular Formula: C9H12O6
- Molecular Weight: 216.19
- SMILES: CC1(O[C@@H]2[C@@H]3[C@@H]([C@@H](C(=O)O3)O)O[C@@H]2O1)C
- Topological: 74.2
- Monoisotopic Mass: 216.06338810
- Synonyms: alpha-D-Glucofuranuronic acid, 1,2-O-(1-methylethylidene)-, gamma-lactone, .alpha.-D-Glucofuranuronic acid, 1,2-O-(1-methylethylidene)-, .gamma.-lactone, 20513-98-8, D-Glucurono-6,3-lactone acetonide, (3aR,3bS,6S,6aR,7aR)-6-Hydroxy-2,2-dimethyltetrahydrofuro[2′,3′:4,5]furo[2,3-d][1,3]dioxol-5(3aH)-one, 1,2-O-Isopropylidene-a-D-glucofuranosidurono-6,3-lactone, (1S,2R,6R,8R,9S)-9-hydroxy-4,4-dimethyl-3,5,7,11-tetraoxatricyclo[6.3.0.02,6]undecan-10-one, 1,2-O-Isopropylidene-alpha-D-glucofuranurono-6,3- lacton, SCHEMBL8220266, BDBGJSXZKMTMGP-UXTLFEIASA-N, D-Glucurono-6,3-Lactone acetonid, AKOS027256613, MI04759, (1S,2R,6R,8R,9S)-9-HYDROXY-4,4-DIMETHYL-3,5,7,11-TETRAOXATRICYCLO[6.3.0.0(2),?]UNDECAN-10-ONE, AS-71845, HY-41840, CS-0019065, 1,2-O-Isopropylidene-?-D-glucofuranurono-6,3-lactone, 1,2-O-Isopropylidene-?-D-glucofuranosidurono-6,3-lactone, |A-D-Glucofuranuronic acid, 1,2-O-(1-methylethylidene)-, |A-lactone
This compound is primarily used as a chiral building block in the synthesis of bioactive molecules and glycoconjugates. Researchers employ it in carbohydrate chemistry to study enzymatic transformations and glycosylation reactions. Its lactone functionality makes it useful in probing metabolic pathways involving glucuronic acid derivatives. Additionally, it serves as a precursor for modified nucleosides in medicinal chemistry applications.
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