492-30-8

Usage

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

• 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 
• 86204-15-1 5-O-benzyl-2-C-methyl 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 
• 93635-76-8 ethyl 4,5-O-isopropylidene-2-C-methyl-DL-lyxonate 
• 93714-03-5 ethyl trans-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-arabinonate 
• 67-64-1 acetone 
• 86204-15-1 5-O benzyl-2-C-methyl ribonolactone 
• 68826-00-6 N-Benzyl-1-methylamino-1-deoxy-β-D-arabino-2-hexulopyranose 
• 57-48-7 D-Fructose 
• 6347-01-9 fructopyranose 

Downstream Products

• 23709-41-3 2-methyl-2,3-O-(1-methylethylidene)-D-ribonic acid γ-lactone 
• 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 
• 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 
• 7392-74-7 C₂₇H₂₂O₈ 
• 7392-74-7 C₂₇H₂₂O₈ 
• 7392-74-7 C₂₇H₂₂O₈ 
• 30361-18-3 3,5-dibenzoyloxy-2-C-methy-β-D-ribofuranose 
• 23643-36-9 2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine 
• 760965-38-6 C₂₉H₂₆O₉ 
• 863329-65-1 (2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate 
• 863329-66-2 2'-deoxy-2'-fluoro-2'-methyluridine 
• 944476-43-1 C₂₄H₂₀N₂O₇ 

Relevant academic research and scientific papers

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.

METHOD FOR PRODUCING LACTONE

PROBLEM TO BE SOLVED: To provide a method for producing a lactone in high yield by using sugar as raw material. SOLUTION: A method for producing a lactone includes a step A of obtaining a lactone by heating sugar raw material in solvent in the presence of a titanium oxide with a crystallite diameter of 8.0 nm or more. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

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).

Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2′-c-methylribonucleosides, arabinonucleosides and 2′-deoxy-2′-fluoroarabinonucleosides

A series of novel sugar-modified derivatives of cytostatic 6-hetaryl-7-deazapurine ribonucleo-sides: 2′-C-methylribonucleosides, arabinonucleosides and 2′-deoxy-2′-fluoroarabinonucleo-sides bearing an alkyl, aryl and hetaryl group in position 6 were prepared by palladium catalyzed cross-coupling reactions of corresponding (protected) 6-chloro-(7-fluoro)-7-deazapurine nucleosides with (het)arylboronic, hetarylstannanes and trimethylaluminium eventually followed by deprotection. Key intermediate 6-chloro-7-deazapurine 2′-C-methyl-β-D-ribofuranoside was prepared via a stereoselective nucleobase anion glycosylation with toluoyl-protected 1,2-anhydro-2-C-methylribofuranose. The 1,2-anhydro sugar was synthesized in 3 steps starting from readily available 2-C-methylribonolactone. The 6-chloro-7-deazapurine arabinofuranoside intermediate was obtained by epimerization from 3′,5′-protected 6-chloro-7-deazapurine ribofuranoside via 2′-hydroxyl oxidation followed by reduction. None of the prepared compounds showed any considerable cytostatic or antiviral activity.

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.

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

Doubly carbon-branched pentoses: synthesis of both enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection

An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-l-erythronolactone [from 2-C-methyl-d-ribono-lactone or d-ribose] and 3-C-methyl-d-erythronolactone [from d-tagatose or l-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous solution.

Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone

Readily crystallized 2-C-methyl-d-ribono-1,4-lactone is formed in a one-pot procedure from d-glucose without any protecting groups by treatment with dimethylamine to give an Amadori ketose and then with aqueous calcium hydroxide in yields of approximately 25%; 2-C-methyl-l-ribono-1,4-lactone is similarly produced from l-glucose. 3,4-O-Isopropylidene-2-C-methyl-d-arabinono-1,5-lactone and 2-C-methyl-d-arabinono-1,4-lactone were prepared in a combined 60% yield by the Kiliani reaction of sodium cyanide with a protected 1-deoxy-d-ribulose derived from d-erythronolactone; the enantiomeric arabinonolactones are similarly available from l-erythronolactone.

Towards the biotechnological isomerization of branched sugars: d-tagatose-3-epimerase equilibrates both enantiomers of 4-C-methyl-ribulose with both enantiomers of 4-C-methyl-xylulose

Microbial oxidation of 2-C-methyl-d-ribitol and 2-C-methyl-d-arabinitol by Gluconobacter thailandicus NBRC 3254 produces 4-C-methyl-l-ribulose and 4-C-methyl-d-ribulose, respectively. Further, 4-C-methyl-l-ribulose and 4-C-methyl-d-ribulose were equilibra

PROCESS FOR PREPARING SACCHARINIC ACIDS AND LACTONES

An improved process for preparing a saccharinic acid or lactone is disclosed that utilizes the well-known Amadori rearrangement reaction. The synthesis utilizes protected or unprotected sugars or their analogues as starting materials, and reagents not pre