908128-94-9

Basic information

• Product Name: 5-O-Methanesulfonate-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone
• Synonyms: 5-O-Methanesulfonate-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone;5-O-Methanesulfonate-2,3-O-isopropylidene-2-C-methyl-D-ribonic-γ-lactone;5-O-Methanesulfonate-2,3-O-isopropylidene-2-C-Methyl-D-ribonic-gMMa-lactone
• CAS NO: 908128-94-9
• Molecular Formula: C₁₀H₁₆O₇S
• Molecular Weight: 280.295
• Mol File: 908128-94-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.330
• CAS DataBase Reference: 5-O-Methanesulfonate-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-O-Methanesulfonate-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone(908128-94-9)
• EPA Substance Registry System: 5-O-Methanesulfonate-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone(908128-94-9)

Safety Data

• Hazardous Substances Data: 908128-94-9(Hazardous Substances Data)

Usage

General Description

5-O-Methanesulfonate-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone is a chemical compound with a complex name that indicates its structure and functional groups. It is a synthetic derivative of ribonic acid, which is a rare sugar found in nature. The compound contains a methanesulfonate group, an isopropylidene group, and a methyl group, all attached to a ribonic-gamma-lactone ring. 5-O-Methanesulfonate-2,3-O-isopropylidene-2-C-methyl-D-ribonic-gamma-lactone has potential applications in organic synthesis and medicinal chemistry due to its unique structure and reactivity. Its specific properties and potential uses would depend on further research and experimentation.

Upstream product

• 492-30-8 2-C-methyl-D-ribono-1,4-lactone 
• 23709-41-3 2-methyl-2,3-O-(1-methylethylidene)-D-ribonic acid γ-lactone 
• 124-63-0 methanesulfonyl chloride 

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.

Green aldose isomerisation: 2-C-methyl-1,4-lactones from the reaction of Amadori ketoses with calcium hydroxide

Saccharinic acids, branched 2-C-methyl-aldonic acids, may be accessed via a green procedure from aldoses by sequential conversion to an Amadori ketose and treatment with calcium hydroxide; d-galactose and d-glucose are converted to 2-C-methyl-d-lyxono-1,4