4099-88-1

Basic information

• Product Name: 2,3-O-Isopropylidene-D-ribofuranose
• Synonyms: (3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol;(1β,5β)-3,3-Dimethyl-8-hydroxy-2,4,7-trioxabicyclo[3.3.0]octane-6β-methanol;(3aβ,6aβ)-6-Hydroxy-2,2-dimethyltetrahydrofuro[3,4-d]-1,3-dioxole-4β-methanol;2-O,3-O-(1-Methylethylidene)-D-ribofuranose;2-O,3-O-Isopropylidene-D-ribo-pentofuranose;2,3-O-Isopropylidene-D-ribofuranose-2
• CAS NO: 4099-88-1
• Molecular Formula: C₈H₁₄O₅
• Molecular Weight: 190.2
• Mol File: 4099-88-1.mol
• Article Data: 182

Chemical Properties

• Boiling Point: 337.4oC at 760 mmHg
• Flash Point: 157.9oC
• Appearance: /
• Density: 1.267g/cm3
• Vapor Pressure: 7.17E-06mmHg at 25°C
• Refractive Index: 1.485
• Storage Temp.: 2-8°C
• PKA: 12.02±0.60(Predicted)
• CAS DataBase Reference: 2,3-O-Isopropylidene-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-O-Isopropylidene-D-ribofuranose(4099-88-1)
• EPA Substance Registry System: 2,3-O-Isopropylidene-D-ribofuranose(4099-88-1)

Safety Data

• Hazardous Substances Data: 4099-88-1(Hazardous Substances Data)

Usage

General Description

2,3-O-Isopropylidene-D-ribofuranose is a chemical compound that is a derivative of D-ribose, a naturally occurring sugar. It is commonly used in organic chemistry as a protecting group for the hydroxyl group of ribose. 2,3-O-Isopropylidene-D-ribofuranose is characterized by the presence of an isopropylidene group attached to the C2 and C3 positions of the ribose molecule, which serves to protect the hydroxyl groups and prevent unwanted reactions during chemical synthesis. 2,3-O-Isopropylidene-D-ribofuranose is an important building block in the synthesis of various pharmaceuticals, natural products, and other bioactive compounds. Its unique structure and reactivity make it a valuable tool for chemists in the manipulation and modification of ribose-containing molecules.

InChI:InChI=1/C8H14O5/c1-8(2)12-5-4(3-9)11-7(10)6(5)13-8/h4-7,9-10H,3H2,1-2H3/t4-,5-,6-,7?/m1/s1

Upstream product

• 87-72-9 D-lyxose 
• 67-64-1 acetone 
• 1114-34-7 D-lyxose 
• 532-20-7 D-lyxose 
• 77-76-9 2,2-dimethoxy-propane 
• 58-86-6 D-xylose 
• 50-69-1 D-ribose 
• 20689-03-6 1-((3aR,4S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol 
• 116780-31-5 (1R)-1-((4R,5S)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 116669-78-4 (4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 41546-21-8 L-ribose 
• 10257-32-6 D-ribose 
• 532-20-7 D-Ribose 

Downstream Products

• 123564-95-4 1,5-di-O-(3,5-dinitrophenyl)carbamoyl-2,3-O-isopropylidene-α-D-lyxofuranose 
• 123564-94-3 5-O-(3,5-dinitrophenyl)carbamoyl-2,3-O-isopropylidene-α-D-lyxofuranose 
• 85220-34-4 ((3aR,4R,6R,6aR)-6-Cyclohexylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol 
• 85220-33-3 ((3aR,4R,6S,6aR)-6-Cyclohexylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol 
• 950182-24-8 (3aR,6R,6aR)-2,2-dimethyl-6-(tosyloxymethyl)-tetrahydro-2H-furo[3,4-d]-1,3-dioxol-4-ol 
• 96690-02-7 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose 
• 85220-26-4 ((3aR,4R,6R,6aR)-6-Benzylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol 
• 85220-25-3 ((3aR,4R,6S,6aR)-6-Benzylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol 
• 95353-02-9 ((3aR,4R,6R,6aR)-6-Dibenzylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol 
• 95352-76-4 (3aR,7R,7aR)-4-Dibenzylamino-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 50-69-1 D-ribose 
• 176245-06-0 1-O-benzoyl-2,3-O-isopropylidene-5-O-p-toluenesulfonyl-β-D-ribose 
• 380883-57-8 1-O-methyl-2,3,5-tris-O-(4-methylbenzoyl)-β-D-[2-2H1]ribofuranose 
• 155934-55-7 (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 

Relevant articles and documents

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.

Synthesis of hydroxymethyl analogues of mannostatin A and their evaluation as inhibitors of GH38 α-mannosidases

A synthetic approach to hydroxymethyl analogues of mannostatin A starting froml-ribose is described. The key step employed in the synthesis of homomannostatin A was ring-opening of aziridine intermediates with sodium methanethiolate in DMF. Regioselectivity of these openings was investigated by quantum mechanics calculations. The synthesised hydroxymethyl analogues of mannostatin A were evaluated as inhibitors of three different GH38 α-mannosidases: the Golgi (GMIIb) and lysosomal (LManII) α-mannosidases fromDrosophila melanogaster, and commercial Jack bean α-mannosidase (JBMan) fromCanavalia ensiformis. The tested compounds exhibited inhibitory activity against GMIIb with IC50values in the range of 3-43 μM resulting in selectivity [IC50(LManII)/IC50(GMIIb)] similar to mannostatin A.

Synthetic Study Aiming at the Tricyclic Core of 12- epi-JBIR-23/24

The synthetic study toward highly enantio- and diastereoselective synthesis of the tricyclic framework of 12-epi-JBIR-23/24, a natural product analogue showing inhibitory activity against four malignant pleural mesothelioma cell lines, is presented herein