Description

3-O-Benzyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (CAS No. 18685-18-2) is a highly specialized carbohydrate derivative extensively used in synthetic organic chemistry and glycoscience research. This compound features a benzyl-protected hydroxyl group at the 3-position and isopropylidene acetal protections at the 1,2- and 5,6-positions, rendering it a versatile intermediate for selective deprotection and further functionalization. With the molecular formula C₁₉H₂₆O₆, it offers excellent stability under various reaction conditions, making it ideal for multi-step synthetic routes. Its IUPAC name, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole, reflects its intricate furanose-based structure. Suitable for researchers in medicinal chemistry, glycobiology, and asymmetric synthesis, this product is supplied with high purity and rigorous QC validation to ensure reproducibility.

Properties

• CAS Number: 18685-18-2
• Complexity: 473
• IUPAC Name: 6-benzyloxy-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• InChI: InChI=1S/C19H26O6/c1-18(2)21-11-13(23-18)14-15(20-10-12-8-6-5-7-9-12)16-17(22-14)25-19(3,4)24-16/h5-9,13-17H,10-11H2,1-4H3
• InChI Key: ZHFVGOMEUGAIJX-UHFFFAOYSA-N
• Exact Mass: 350.17293854
• Molecular Formula: C19H26O6
• Molecular Weight: 350.4
• SMILES: CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)OCC4=CC=CC=C4)C
• Topological: 55.4
• Monoisotopic Mass: 350.17293854
• Synonyms: 18685-18-2, 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole, NSC 56267, BRN 0043822, 3-O-Benzyl-1,2:5,6-Di-O-isopropylidene-a-D-glucofuranose, NSC56267, 1,2:5,6-Bis-O-(1-methylethylidene)-3-O-(phenylmethyl)-alpha-D-glucofuranose, alpha-D-Glucofuranose, 1,2:5,6-bis-O-(1-methylethylidene)-3-O-(phenylmethyl)-, SCHEMBL2312455, (4R)-4-[(3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]-2,2-dimethyl-1,3-dioxolane, NSC-56267, AKOS030254888, MB04263, PS-11003, SY246335, 3-0-benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose, 3-O-Benzyl 1,2:5,6,-di-O-isopropylidene-alpha-D-glucofuranose, .alpha.D-Galactofuranose, 1,2:5,6-bis-O-(1-methylethylidene)-3-O-(phenylmethyl)-, (3aR,5R)-6-[(Benzyl-4-D)oxy]-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole, 6-Benzyloxy-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Application

This compound serves as a key intermediate in the synthesis of complex carbohydrates, nucleosides, and glycoconjugates. It is widely employed in the preparation of selectively protected sugar derivatives for oligosaccharide assembly. Researchers utilize it in glycosylation reactions to study stereoselective bond formation. Its stability under acidic and basic conditions makes it valuable for multi-step organic transformations.

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