492-30-8

Basic information

• Product Name: 2-C-Methyl-D-ribono-1,4-lactone
• Synonyms: 3,4-Dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one;(3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one;3,4-dihydroxy-3-methyl-5-methylol-tetrahydrofuran-2-one;2-C-Methyl-;2-C-Methyl-D-ribonoic-1,4-lactone;2-C-metylribono-γ-lactone;D-Ribonic acid, 2-C-methyl-, γ-lactone;2-C-Methyl-D-ribonoicacid-1,4-Lactone
• CAS NO: 492-30-8
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.14
• EINECS: 1312995-182-4
• Product Categories: Carbohydrates & Derivatives
• Mol File: 492-30-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 150-160°C
• Boiling Point: 338.3 °C at 760 mmHg
• Flash Point: 145.6 °C
• Appearance: /
• Density: 1.512 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.551
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 12.12±0.60(Predicted)
• CAS DataBase Reference: 2-C-Methyl-D-ribono-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-C-Methyl-D-ribono-1,4-lactone(492-30-8)
• EPA Substance Registry System: 2-C-Methyl-D-ribono-1,4-lactone(492-30-8)

Safety Data

• Hazardous Substances Data: 492-30-8(Hazardous Substances Data)

Usage

Chemical Properties

2-C-Methyl-D-ribono-1,4-lactone is White to Off-White Solid

Uses

2-C-Methyl-D-ribono-1,4-lactone is used in synthesis of enantiomerically pure 4-substituted riboses; also for preparing saccharinic acids and lactones via Amadori rearrangement for use as synthons toward herbicidal esters and branched nucleosides.

InChI:InChI=1/C6H10O5/c1-6(10)4(8)3(2-7)11-5(6)9/h3-4,7-8,10H,2H2,1H3/t3-,4-,6-/m1/s1

Upstream product

• 874351-61-8 C₈H₁₇NO₅ 
• 25581-41-3 D-erythronolactone acetonide 
• 75-16-1 methylmagnesium bromide 
• 773837-37-9 sodium cyanide 
• 138811-35-5 1-Deoxy-3,4-O-isopropylidene-D-erythro-2-pentulofuranose 
• 69712-22-7 1-deoxy-1-dibenzylamino-D-fructose 
• 93635-76-8 ethyl 4,5-O-isopropylidene-2-C-methyl-DL-arabinonate 
• 93635-76-8 ethyl 4,5-O-isopropylidene-2-C-methyl-DL-lyxonate 
• 86204-05-9 (2S,3R)-3,5-Bis-benzyloxy-2-hydroxy-2-methyl-4-oxo-pentanoic acid methyl ester 
• 86204-14-0 5-Benzyloxymethyl-3-methyl-5H-furan-2-one 
• 86204-09-3 3,5-O-dibenzyl-2-C-methyl-DL-lyxonolactone 
• 93635-76-8 ethyl 4,5-O-isopropylidene-2-C-methyl-DL-ribonate 
• 93714-02-4 ethyl cis-2,3-dideoxy-4,5-O-isopropylidene-2-C-methyl-DL-glycero-pent-2-enonate 
• 93636-16-9 ethyl 2-C-methyl-DL-ribonate 

Downstream Products

• 23709-41-3 2-methyl-2,3-O-(1-methylethylidene)-D-ribonic acid γ-lactone 
• 23709-41-3 2,3-O-isopropylidene-2-C-methyl-DL-lyxono-1,4-lactone 
• 23709-41-3 2,3-O-isopropylidene-2-C-methyl-DL-ribono-1,4-lactone 
• 105-43-1 3-methylvaleric acid 
• 64-18-6 formic acid 
• 79-14-1 glycolic Acid 
• 64-19-7 acetic acid 
• 25137-77-3 3,5-di-O-(4-methylbenzoyl)-2-C-methyl-D-ribono-γ-lactone 
• 53008-95-0 2-C-methyl-2,3,5-tri-O-(4-methylbenzoyl)-D-ribono-1,4-lactone 
• 30361-18-3 3,5-dibenzoyloxy-2-C-methy-β-D-ribofuranose 
• 917567-08-9 (3R,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-3-methyloxolan-2-one 
• 1157884-58-6 ((2R,3R,4S)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methylbenzoate 

Relevant articles and documents

A process for preparing 2 - C - methyl - D - ribotide - 1, 4 - lactone

The invention relates to a method for preparing 2-C-methyl-D-ribotide-1,4-lactone, which comprises the following steps: adding a raw material D-glucose into dibenzyl amine, acetic acid and ethanol at room temperature, dissolving by stirring, heating, and refluxing to generate 1-desoxy-1-(N,N-amino)-D-fructose; after finishing the reaction, cooling to room temperature to obtain a white solid, drying to obtain 1-desoxy-1-(N,N-amino)-D-fructose, dissolving the 1-desoxy-1-(N,N-amino)-D-fructose and CaO in ethanol and water by stirring, and heating under reflux; and after finishing the reaction, cooling, carrying out centrifugal drying to remove the solvent, adding water and oxalic acid hydrate to precipitate abundant calcium oxalate, filtering, washing, carrying out centrifugal drying on the filtrate to obtain a black viscous liquid, adding acetone, cooling by standing, and recrystallizing with acetone to obtain the 2-C-methyl-D-ribotide-1,4-lactone. The method has the advantages of reasonable technique, low cost, short reaction time and high yield, and is simple to operate.

PROCESS FOR THE PREPARATION OF 2-C-METHYL-D-RIBONIC-GAMMA-LACTONE

Disclosed is a process to prepare a ribonolactone compound of Formula (I):[PLEASE INSERT CHEMICAL STRUCTURE HERE] comprising the step of reacting a fructosamine compound of Formula (II):[PLEASE INSERT CHEMICAL STRUCTURE HERE] in the presence of a calcium salt and a base in a nonaqueous reaction medium, to provide said ribonolactone compound of Formula (I).

2-C-Methyluridine modified hammerhead ribozyme against the estrogen receptor

A new synthesis of 2′-C-methyluridine phosphoramidite is presented. Special emphasis is dedicated to the improvement of the protection of the tertiary 2′-hydroxyl group. Comparison to previous protecting strategies and analysis of stability under 5′-DMTr removing conditions are discussed. The synthetic incorporation of this modified nucleoside into the catalytic core of a hammerhead ribozyme against the estrogen receptor α protein (ER-α), and transfection experiments in MCF-7 cell line are also presented.