863396-35-4

Usage

Uses

Used in Pharmaceutical Industry:
Decitabine iMpurity 4 is used as a reference compound for quality control and analytical purposes in the development and manufacturing of Decitabine, a DNA hypomethylating agent. By inhibiting DNA methyltransferase, Decitabine silences tumor suppressor genes and "normalizes" gene expression in cancerous cells, making it effective in treating myelogeneous leukemia and metastatic lung cancer.

Upstream product

• 67-56-1 methanol 
• 452-51-7 D-2-deoxyribose 
• 533-67-5 2-Deoxy-D-ribose 
• 22900-10-3 2-deoxy-D-ribose 

Downstream Products

• 916593-22-1 C₂₀H₂₄O₈S₂ 
• 94292-83-8 (7E,9E,11E,13E)-(5S,6R,15S)-5,6,15-Trihydroxy-icosa-7,9,11,13-tetraenoic acid 
• 89663-86-5 lipoxin A₄ 
• 22900-10-3 (4R,5S)-tetrahydro-2H-pyran-2,4,5-triol 
• 152039-44-6 methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methylbenzenesulfonyl)-D-erythro-pentofuranoside 

Relevant academic research and scientific papers

Chelation-controlled regioselective endo cleavage and stereoselective C-1 alkylation of pentofuranosides

Combinations of Lewis acids and nucleophilic reagents trigger endo-opening of the furanoside ring of methyl furanosides 1, 10 and 13, resulting in the attachment of the nucleophilic group at C-1 of the carbohydrate. The stereoselectivity in the C-C bond-f

Synthesis and DNA/RNA Binding Properties of Conformationally Constrained Pyrrolidinyl PNA with a Tetrahydrofuran Backbone Deriving from Deoxyribose

Sugar-derived cyclic β-amino acids are important building blocks for designing of foldamers and other biomimetic structures. We report herein the first synthesis of a C-activated N-Fmoc-protected trans-(2S,3S)-3-aminotetrahydrofuran-2-carboxylic acid as a building block for Fmoc solid phase peptide synthesis. Starting from 2-deoxy-d-ribose, the product is obtained in a 6.7% overall yield following an 11-step reaction sequence. The tetrahydrofuran amino acid is used as a building block for a new peptide nucleic acid (PNA), which exhibits excellent DNA binding affinity with high specificity. It also shows preference for binding to DNA over RNA and specifically in the antiparallel orientation. In addition, the presence of the hydrophilic tetrahydrofuran ring in the PNA structure reduces nonspecific interactions and self-aggregation, which is a common problem in PNA due to its hydrophobic nature.

PROCESS FOR THE PREPARATION OF (2R.3S)-2-(HYDROXYMETHYL) -5-METHOXYTETRAHYDROFURAN-3-OL AND ACETYLATED DERIVATIVES THEREOF, FREE OF PYRANOSE COMPOUNDS

A method of preparing a ribofuranose derivative essentially free of pyranose compounds includes a step of contacting a solution of MDR containing MDRP as an impurity in a solvent including methanol and/or tetrahydrofuran with at least one alkali metal periodate under conditions sufficient to oxidize at least a portion of the MDRP. MDR containing at most 5 wt% of MDRP based on the total weight of MDR and MDRP may be produced.

A greener enantioselective synthesis of the antiviral agent North-methanocarbathymidine (N-MCT) from 2-deoxy-d-ribose

An enantioselective synthesis of suitably protected (1R,2S,4S,5S)-4-amino-1-(hydroxymethyl)bicyclo[3.1.0]hexan-2-ol, a key starting material for the synthesis of conformationally locked carbocyclic nucleosides, including the antiviral active North-methano

A simple and efficient synthesis of 2-deoxy-L-ribose from 2-deoxy-D-ribose

An efficient synthesis of 2-deoxy-L-ribose was achieved without chromatography starting from its enantiomer 2-deoxy-D-ribose in more than 30% overall yield. An unexpected product, 2-deoxy-xylose, was obtained under slightly different reaction conditions a

Synthesis of 2,3'-anhydro-2'-deoxyuridines and 2,3'-didehydro-2',3'-dideoxyuridines using polymer supported fluoride

Reaction of methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-α,β-D-eryt hro-pentofuranoside (2) with silylated uracils 3 using trimethylsilyl trifluoromethanesulfonate (TMS triflate) as catalyst afforded after crystallization in Et2O the corresponding β-nucleosides 4. Reaction of 4 with tetrabutylammonium fluoride (TBAF) or Amberlyst A-26 resin (F--form) in THF at room temperature or at reflux gave the corresponding deprotected 2,3'-anhydro-2'-deoxyuridines 6 and 2',3'-didehydro-2',3'-dideoxyuridines 7, respectively.

Enantiospecific and Stereospecific Synthesis of Lipoxin A. Stereochemical Assignment of the Natural Lipoxin A and Its Possible Biosynthesis

Both chemical and enzymatic steps were employed to convert leukotriene A4 and its unnatural epoxide isomers into four diastereomeric 5(S),6(S),15(S)-trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acids, possible structures for lipoxin A.These compounds were correlated with trihydroxy tetraene eicosatetraenoic acids derived from tetraene epoxide 3, and the relative stereochemistries of the 5 and 6 positions were assigned.These assignments were confirmed by total synthesis of two diastereomers of lipoxin A.One of these isomers, 5(S),6(S),15(S)-trihydroxy-7-9,13-trans-11-cis-eicosatetraenoic acid (1b), corresponded to lipoxin A derived from natural sources.The structure and possible biosyntheses of lipoxin A are proposed.