23709-41-3

Basic information

• Product Name: 2,3-O-Isopropylidene-2-C-methyl-D-ribonic-gamma-lactone
• Synonyms: 2,3-O-Isopropylidene-2-C-methyl-D-ribonic-gamma-lactone;2,3-O-(1-Methylethylidene)-2-C-methyl-D-ribonic-γ-lactone;2,3-O-Isopropylidene-2-C-Methyl-D-ribonic Acid γ-Lactone;2-C-Methyl-2,3-O-(1-Methylethylidene)-D-ribonic Acid γ-Lactone;2-C-Methyl-2,3-O-isopropylidene-D-ribono-1,4-lactone
• CAS NO: 23709-41-3
• Molecular Formula: C₉H₁₄O₅
• Molecular Weight: 162.14
• Product Categories: Carbohydrates & Derivatives;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 23709-41-3.mol
• Article Data: 19

Chemical Properties

• Melting Point: 52-54 °C
• Boiling Point: 328 °C
• Flash Point: 130 °C
• Appearance: /
• Density: 1.230
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.68±0.10(Predicted)
• CAS DataBase Reference: 2,3-O-Isopropylidene-2-C-methyl-D-ribonic-gamma-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-O-Isopropylidene-2-C-methyl-D-ribonic-gamma-lactone(23709-41-3)
• EPA Substance Registry System: 2,3-O-Isopropylidene-2-C-methyl-D-ribonic-gamma-lactone(23709-41-3)

Safety Data

• Hazardous Substances Data: 23709-41-3(Hazardous Substances Data)

Usage

Description

2,3-O-Isopropylidene-2-C-methyl-D-ribonic-gamma-lactone is a complex organic compound that serves as a key intermediate in the synthesis of various biologically active molecules. It is characterized by its unique structure, which includes an isopropylidene group and a methyl group at the 2-C position, as well as a gamma-lactone ring. 2,3-O-Isopropylidene-2-C-methyl-D-ribonic-gamma-lactone plays a crucial role in the development of pharmaceuticals and other applications due to its versatile chemical properties.

Uses

Used in Pharmaceutical Industry:
2,3-O-Isopropylidene-2-C-methyl-D-ribonic-gamma-lactone is used as a synthetic intermediate for the production of carbon-branched carbohydrate chirons. These chirons are essential building blocks in the synthesis of enantiomers of 2-C-Methyl-ribono-1,4-lactone (M325961) and 2-C-Methyl-arabinonolactone. These enantiomers are vital components in the development of Neplanocyn A, a potential anti-HCV (hepatitis C virus) agent. The compound's role in the synthesis of these chirons highlights its importance in the pharmaceutical industry, particularly in the development of novel treatments for viral infections.

Upstream product

• 53008-90-5 2-C-methyl-D-arabino-γ-lactone 
• 492-30-8 2-C-methyl-D-ribono-1,4-lactone 
• 67-64-1 acetone 
• 77-76-9 2,2-dimethoxy-propane 
• 116-11-0 2-Methoxypropene 
• 492-30-8 2-C-methyl-DL-lyxono-1,4-lactone 
• 93714-02-4 ethyl cis-2,3-dideoxy-4,5-O-isopropylidene-2-C-methyl-DL-glycero-pent-2-enonate 
• 93635-76-8 ethyl 4,5-O-isopropylidene-2-C-methyl-DL-lyxonate 
• 492-30-8 2-C-methyl-DL-ribono-1,4-lactone 
• 93636-16-9 ethyl 2-C-methyl-DL-ribonate 
• 93635-76-8 ethyl 4,5-O-isopropylidene-2-C-methyl-DL-ribonate 

Downstream Products

• 144363-76-8 5-O-benzyl-2,3-di-O-isopropyliden-2-C-methylribono-γ-lactone 
• 109715-12-0 2,3-O-Isopropyliden-2-C-methyl-5-O-p-toluolsulfonyl-D-ribo-pentonsaeure-γ-lacton 
• 157666-07-4 5-Bromo-2,3-O-isopropylidene-2-C-methyl-D-ribono-1,4-lactone 
• 908128-94-9 2,3-O-isopropylidene-5-O-methanesulfonyl-2-C-methyl-D-ribono-1,4-lactone 
• 84911-69-3 benzyl 2(S)-(5(S)-(hydroxymethyl)-3(S)-methyl-2(S)-tetrahydrofuryl)butyl ether 

Relevant articles and documents

Asymmetric Synthesis of 2′- C-Methyl-4′-selenonucleosides as Anti-Hepatitis C Virus Agents

In search of a new template for anti-hepatitis C virus (HCV) agents, we designed and synthesized the 2′-C-methyl-4′-selenopyrimidine and -purine nucleosides and their phosphoramidate prodrugs to replace a furanose oxygen of anti-HCV nucleos(t)ides with a selenium atom on the basis that selenium is a chemical isostere of oxygen. These nucleosides are expected to show different physicochemical properties such as better lipophilicity which might enhance the penetration across cell membranes and the conformational constraint induced by a bulky selenium atom in the sugar ring. The 2′-C-methyl-4′-selenopyrimidine and -purine nucleosides 8 and 9 were synthesized from 2-C-methyl-d-ribono-γ-lactone (14) via construction of 2-C-methyl-d-selenosugar 18 through C-4 epimerization and SN2 cyclization with Se2- as key steps. The key 4′-selenosugar was converted to the 2′-C-methyl-4′-selenopyrimidine and -purine nucleosides using Pummerer-type rearrangement and Vorbrüggen glycosylation, respectively. In addition, the ProTide strategy has been applied to synthesize the adenine and uracil phosphoramidate derivatives 10a and 10b to overcome the limitations associated with parent nucleosides such as inefficient conversion to their corresponding 5′-monophosphate form and poor cellular uptake. The regio- and stereochemistry of 4′-selenonucleosides were confirmed by 2D NOESY NMR spectroscopy and X-ray crystallography. None of the final pyrimidine and purine nucleosides and their prodrugs exhibited significant anti-HCV activity up to 100 μM.

Homochiral carbon branched piperidines from carbon branched sugar lactones: 4-C-methyl-deoxyfuconojirimycin (DFJ) and its enantiomer-removal of glycosidase inhibition

The value of readily available 2-C-methyl aldonic acids in short syntheses of carbon branched piperidines containing quaternary centers is demonstrated. The effect of the introduction of a 4-C-methyl group into piperidine imino sugar inhibitors of l-fucosidases and d-galactosidases is reported.

PHOTOACID GENERATOR, PHOTORESIST COMPRISING THE PHOTOACID GENERATOR, AND COATED ARTICLE COMPRISING SAME

A photoacid generator has the formula (I): wherein R1, R2, R3, L1, L2, L3 X, Z+, a, b, c, d, p, q, and r, are defined herein. A photoresist comprises the photoacid generator, and a coated article comprises the photoresist. The photoresist can be used to form an electronic device.

SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF

Disclosed herein are nucleosides, nucleotides and nucleotide analogs, methods of synthesizing the same and methods of treating diseases and/or conditions such as a Coronaviridae virus, a Togaviridae virus, a Hepeviridae virus and/or a Bunyaviridae virus infection with one or more nucleosides, nucleotides and nucleotide analogs.