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

Description

2-C-Methyl-D-ribono-1,4-lactone is an organic compound that is a derivative of ribose, a sugar molecule. It is characterized by its white to off-white solid appearance and is known for its role in the synthesis of various chemical compounds.

Uses

Used in Pharmaceutical and Chemical Industries:
2-C-Methyl-D-ribono-1,4-lactone is used as a key intermediate in the synthesis of enantiomerically pure 4-substituted riboses. These riboses are essential building blocks for the development of novel pharmaceutical compounds with potential applications in the treatment of various diseases.
Used in Agricultural Industry:
In the agricultural sector, 2-C-Methyl-D-ribono-1,4-lactone is utilized for preparing saccharinic acids and lactones through the Amadori rearrangement process. These compounds serve as synthons, or synthetic precursors, for the development of herbicidal esters. These herbicidal esters are used to control the growth of unwanted plants, thereby improving crop yield and quality.
Used in Nucleoside Synthesis:
2-C-Methyl-D-ribono-1,4-lactone also plays a crucial role in the synthesis of branched nucleosides, which are important components of nucleic acids like DNA and RNA. These branched nucleosides have potential applications in the development of new antiviral and anticancer drugs, as well as in the study of genetic information and its manipulation.

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

• 50-99-7 D-glucose 
• 57-48-7 D-Fructose 
• 86204-15-1 5-O benzyl-2-C-methyl ribonolactone 
• 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 
• 86204-15-1 5-O-benzyl-2-C-methyl lyxonolactone 
• 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 
• 93714-03-5 ethyl trans-2,3-dideoxy-4,5-O-isopropylidene-2-C-methyl-DL-glycero-pent-2-enonate 
• 67-64-1 acetone 

Downstream Products

• 23669-85-4 2-C-Methyl-D-ribose-N-benzyl-N-phenylhydrazon 
• 7392-74-7 C₂₇H₂₂O₈ 
• 7392-74-7 C₂₇H₂₂O₈ 
• 7392-74-7 C₂₇H₂₂O₈ 
• 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 
• 64-18-6 formic acid 
• 849585-22-4 LACTIC ACID 
• 75-47-8 iodoform 
• 105-43-1 3-methylvaleric acid 
• 79-14-1 glycolic Acid 
• 64-19-7 acetic acid 
• 908128-94-9 2,3-O-isopropylidene-5-O-methanesulfonyl-2-C-methyl-D-ribono-1,4-lactone 

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).

Total synthesis of neomethymycin and novamethymycin

Total synthesis of neomethymycin and novamethymycin has been achieved. These two macrolides contains 12-membered macrolactones as aglycones and belong to the methymycin family of antibiotics, which appears in the pikromycin biosynthetic pathway. The segme