Description

1,2,3,4-Di-O-isopropylidene-alpha-D-fucopyranose (CAS No. 4026-27-1) is a highly specialized carbohydrate derivative with the molecular formula C₁₂H₂₀O₅. This compound, also known by its IUPAC name (1S,2R,6R,8R,9S)-4,4,8,11,11-pentamethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0^2,6]dodecane, is a protected form of fucose, featuring isopropylidene groups that enhance its stability and reactivity in synthetic applications. It is widely utilized in organic synthesis, glycochemistry, and as a chiral building block for complex molecular architectures. The compound is supplied as a high-purity solid, ensuring optimal performance in sensitive reactions. Its unique stereochemistry makes it invaluable for researchers developing glycosides, glycoconjugates, and other bioactive molecules.

Properties

• CAS Number: 4026-27-1
• Complexity: 327
• IUPAC Name: (1S,2R,6R,8R,9S)-4,4,8,11,11-pentamethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• InChI: InChI=1S/C12H20O5/c1-6-7-8(15-11(2,3)14-7)9-10(13-6)17-12(4,5)16-9/h6-10H,1-5H3/t6-,7+,8+,9-,10-/m1/s1
• InChI Key: FBWQLTARTKWGMT-SOYHJAILSA-N
• Exact Mass: 244.13107373
• Molecular Formula: C12H20O5
• Molecular Weight: 244.28
• SMILES: C[C@@H]1[C@H]2[C@@H]([C@@H]3[C@H](O1)OC(O3)(C)C)OC(O2)(C)C
• Topological: 46.2
• Monoisotopic Mass: 244.13107373
• Synonyms: 4026-27-1, 1,2,3,4-Di-O-isopropylidene-alpha-D-fucopyranose, 1,2:3,4-di-O-Isopropylidene-D-fucopyranose, 6-Deoxy-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose, (1S,2R,6R,8R,9S)-4,4,8,11,11-pentamethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane, 1,2,3,4-Di-O-isopropylidene-a-D-fucopyranose, MFCD00190867, SCHEMBL3330131, SCHEMBL13328902, MD05797, CS-0452273, 1,2:3,4-Di-O-isopropylidene-a-D-fucopyranose, G84278, (1S,2R,6R,8R,9S)-4,4,8,11,11-pentamethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0,dodecane, (3AR,5R,5aS,8aS,8bR)-2,2,5,7,7-pentamethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran, 6-DEOXY-1:2,3:4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTOPYRANOSE, 1:2,3:4-DI-O-ISOPROPYLIDENE-ALPHA-D-FUCOSE

Application

1,2,3,4-Di-O-isopropylidene-alpha-D-fucopyranose is primarily used as a protected intermediate in the synthesis of fucose-containing glycoconjugates and oligosaccharides. It serves as a key precursor in carbohydrate chemistry for the preparation of glycosyl donors and acceptors. Researchers employ this compound in the study of glycosylation reactions and enzymatic processes involving fucose. Its stability under various conditions makes it suitable for multi-step synthetic routes in medicinal chemistry and glycobiology.

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