Description

2,3:5,6-Di-O-isopropylidene-alpha-D-mannofuranose (CAS No. 14131-84-1) is a highly specialized carbohydrate derivative widely used in organic synthesis and pharmaceutical research. This compound, with the molecular formula C₁₂H₂₀O₆, features a protected mannofuranose structure with two isopropylidene groups, enhancing its stability and reactivity for selective glycosylation and chiral intermediate applications. It is a white to off-white crystalline powder with high purity (>98%), making it ideal for asymmetric synthesis, nucleoside chemistry, and glycobiology studies. The product is rigorously tested for quality, including HPLC, NMR, and mass spectrometry, ensuring consistency for demanding research applications. Packaged under inert gas to prevent moisture absorption and degradation, it is available in quantities ranging from milligrams to kilograms to meet both lab-scale and industrial needs.

Properties

• CAS Number: 14131-84-1
• Complexity: 341
• IUPAC Name: (3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• InChI: InChI=1S/C12H20O6/c1-11(2)14-5-6(16-11)7-8-9(10(13)15-7)18-12(3,4)17-8/h6-10,13H,5H2,1-4H3/t6-,7-,8+,9+,10+/m1/s1
• InChI Key: JWWCLCNPTZHVLF-ZJDVBMNYSA-N
• Exact Mass: 260.12598835
• Molecular Formula: C12H20O6
• Molecular Weight: 260.28
• SMILES: CC1(OC[C@@H](O1)[C@@H]2[C@H]3[C@@H]([C@H](O2)O)OC(O3)(C)C)C
• Topological: 66.4
• Monoisotopic Mass: 260.12598835
• Synonyms: 14131-84-1, 2,3:5,6-Di-O-isopropylidene-alpha-D-mannofuranose, Diaceton-alpha-D-mannofuranose, 2,3:5,6-Di-O-isopropylidene-a-D-mannofuranose, (3aS,4S,6R,6aS)-6-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol, D-Mannose diacetonide, Diacetone-D-mannose, 2,3:5,6-Bis-O-(1-methylethylidene)-D-mannofuranose; NSC 89873;, (3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol, MFCD00134206, 2,3:5,6-Di-O-isopropylidene-|A-D-mannofuranose, SCHEMBL1561267, (3aS,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-ol, AKOS024259118, HY-W101129, MD01051, AS-15216, D90065, 2,3:5,6-Di-O-isopropylidene-?-D-mannofuranose, 2,3,5,6-Di-O-isopropylidene-I+/–D-mannofuranose, 2,3:5,6-Di-O-isopropylidene- alpha -D-mannofuranose

2,3:5,6-Di-O-isopropylidene-alpha-D-mannofuranose is a key intermediate in the synthesis of complex carbohydrates, nucleosides, and glycoconjugates. It serves as a chiral building block for asymmetric organic reactions and is widely used in medicinal chemistry for drug development. The compound’s protected furanose structure facilitates selective functionalization in glycosylation protocols. Researchers also employ it in enzymatic studies and as a precursor for fluorescent sugar analogs. Its stability under acidic conditions makes it valuable for multistep synthetic routes.

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