14440-57-4

Basic information

• Product Name: 6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl acetate (non-preferred name)
• CAS NO: 14440-57-4
• Molecular Formula: C₁₄H₂₂O₇
• Molecular Weight: 302.3203
• Mol File: 14440-57-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 358°C at 760 mmHg
• Flash Point: 155.1°C
• Density: 1.25g/cm³
• Vapor Pressure: 2.62E-05mmHg at 25°C
• Refractive Index: 1.501
• CAS DataBase Reference: 6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl acetate (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl acetate (non-preferred name)(14440-57-4)
• EPA Substance Registry System: 6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl acetate (non-preferred name)(14440-57-4)

Safety Data

• Hazardous Substances Data: 14440-57-4(Hazardous Substances Data)

Upstream product

• 530-26-7 D-Mannose 
• 3458-28-4 D-Mannose 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 144651-34-3 3,6-anhydro-1,2:4,5-di-O-isopropylidene-D-glycero-D-manno-heptitol 
• 108-24-7 acetic anhydride 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 64-19-7 acetic acid 
• 693-13-0 diisopropyl-carbodiimide 

Downstream Products

• 161365-08-8 (R)-2-((3aS,4R,6S,6aS)-6-Allyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-benzyloxy-ethanol 
• 714967-29-0 1-O-acetyl-5-azido-5-deoxy-2,3-O-isopropylidene-6-O-trityl-β-L-gulofuranose 
• 714967-28-9 1-O-acetyl-2,3-O-isopropylidene-6-O-trityl-α-D-mannofuranose 
• 714967-39-2 1,6-di-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenylureido)-β-L-gulofuranose 
• 714967-33-6 1-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenylthioureido)-β-L-gulofuranose 

Relevant articles and documents

Quantitation of monosaccharide isotopic enrichment in physiologic fluids by electron ionization or negative chemical ionization GC/MS using Di-O-isopropylidene derivatives

The aldonitrile pentaacetate and other derivatives lack ions in the electron ionization (EI) spectra possessing an intact hexose structure and thus must be analyzed by chemical ionization GC/MS in order to study multiple isotopomers. We report methods for quantitation of hexose di-O-isopropylidene acetate (IPAc) or pentafluorobenzoyl (PFBz) esters. These were prepared in a two-step procedure using inexpensive reagents that do not adversely impact the isotopomer structure of the sugar. The acetate derivative possesses an abundant [M - CH3] ion in the EI spectrum which is suitable for quantitative analysis of isotopomers. The negative chemical ionization (NCI) spectrum of the corresponding pentafluorobenzoyl derivative has a dominant molecular anion. Moreover, the PFBz derivative is about 100-fold more sensitive than the acetate, which offers some advantages for analysis of minor hexoses found in plasma. Isotopic calibration curves of [U-13C]glucose are linear over the 0.1-60% tracer/tracee range tested. The useful range for isotopic tracer studies is 25-2500 pmol for EI analysis of the acetate derivative and 0.1-55 pmol for NCI analysis of PFBz derivative (sample amount injected). For most studies where sample size is not limited, EI-GC/MS analysis of the IPAc derivative is preferred. NCI-GC/MS analysis is reserved when sample size is limiting or when studies involve hexoses other than glucose that are normally present at low concentration.

Chemoselective and Diastereoselective Synthesis of C-Aryl Nucleoside Analogues by Nickel-Catalyzed Cross-Coupling of Furanosyl Acetates with Aryl Iodides

Canonical nucleosides are vulnerable to enzymatic and chemical degradation, yet their stable mimics—C-aryl nucleosides—have demonstrated potential utility in medicinal chemistry, chemical biology, and synthetic biology, although current synthetic methods remain limited in terms of scope and selectivity. Herein, we report a cross-electrophile coupling to prepare C-aryl nucleoside analogues from readily available furanosyl acetates and aryl iodides. This nickel-catalyzed modular approach is characterized by mild reaction conditions, broad substrate scope, excellent β-selectivity, and high functional-group compatibility. The exclusive chemoselectivity with respect to the aryl iodide enables efficient preparation of a variety of C-aryl halide furanosides suitable for various downstream transformations. The practicality of this transformation is demonstrated through the synthesis of a potent analogue of a naturally occurring NF-κB activator.

A convenient preparation of 5-benzyl ethers of D-gluco- and D-manno-furanose derivatives

Keywords: Glucofuranose; Mannofuranose; Selective benzylation; Two-phase benzylation