947605-23-4

Basic information

• Product Name: (2R,3S,5R)-5-methyltetrahydrofuran-2,3,4-triol
• Synonyms: 5-Deoxy-D-erythro-pentofuranose
• CAS NO: 947605-23-4
• Molecular Formula: C₅H₁₀O₄
• Molecular Weight: 134.13
• Mol File: 947605-23-4.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 277.7°C at 760 mmHg
• Flash Point: 121.7°C
• Density: 1.478g/cm³
• Vapor Pressure: 0.000548mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: (2R,3S,5R)-5-methyltetrahydrofuran-2,3,4-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,5R)-5-methyltetrahydrofuran-2,3,4-triol(947605-23-4)
• EPA Substance Registry System: (2R,3S,5R)-5-methyltetrahydrofuran-2,3,4-triol(947605-23-4)

Safety Data

• Hazardous Substances Data: 947605-23-4(Hazardous Substances Data)

Upstream product

• 27821-07-4 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose 
• 37105-93-4 1,2-O-isopropylidene-5-deoxy-α-D-ribofuranose 
• 109536-53-0 5-deoxy-1,2-isopropylidene-3-O-(p-methoxybenzyl)-α-D-ribofuranose 
• 158112-53-9 (3aR,6R,6aR)-2,2,6-trimethyltetrahydro-2H-furo(3,4-d)(1,3)dioxol-4-ol 
• 4152-79-8 1,2-O-isopropylidene-5-methyl-5-deoxy-α-D-xylofuranose 
• 93978-94-0 5-deoxy-L-arabinose 
• 76647-70-6 (3R,4R,5S)-3,4-dihydroxy-5-methyldihydrofuran-2(3H)-one 
• 93978-94-0 5-deoxy-L-ribose 
• 18555-65-2 L-5-deoxy-ribose 
• 78341-97-6 1-O-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose 
• 532-20-7 D-Ribose 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 52305-57-4 (3aS,4S,6aR)-4-(chloromethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 50610-99-6 1-O-methyl-2,3-O-isopropylidene-5-O-(methanesulfonyl)-β-D-ribofuranoside 

Downstream Products

• 13039-78-6 5-deoxy-L-xylose aldehyde 
• 113421-83-3 5-deoxy-L-xylose hydrate 
• 113421-73-1 5-deoxy-β-L-xylose 
• 93978-94-0 5-deoxy-L-arabinose 
• 93978-94-0 5-deoxy-L-ribose 
• 62933-57-7 1',2'-O-diacetyl-L-biopterin 
• 79698-09-2 (2S,3R,4R,5R)-2-Aminomethyl-5-methyl-tetrahydro-furan-3,4-diol 
• 81827-31-8 2-N-acetyl-1',2'-di-O-acetyl-L-erythro-biopterin 

Relevant articles and documents

Williams–Beuren syndrome-related methyltransferase WBSCR27: cofactor binding and cleavage

Williams–Beuren syndrome, characterized by numerous physiological and mental problems, is caused by the heterozygous deletion of chromosome region 7q11.23, which results in the disappearance of 26 protein-coding genes. Protein WBSCR27 is a product of one of these genes whose biological function has not yet been established and for which structural information has been absent until now. Using NMR, we investigated the structural and functional properties of murine WBSCR27. For protein in the apo form and in a complex with S-(5′-adenosyl)-l-homocysteine (SAH), a complete NMR resonance assignment has been obtained and the secondary structure has been determined. This information allows us to attribute WBSCR27 to Class I methyltransferases. The interaction of WBSCR27 with the cofactor S-(5′-adenosyl)-l-methionine (SAM) and its metabolic products – SAH, 5′-deoxy-5′-methylthioadenosine (MTA) and 5′-deoxyadenosine (5′dAdo) – was studied by NMR and isothermal titration calorimetry. SAH binds WBSCR27 much tighter than SAM, leaving open the question of cofactor turnover in the methylation reaction. One possible answer to this question is the presence of weak but detectable nucleosidase activity for WBSCR27. We found that the enzyme catalyses the cleavage of the adenine moiety from SAH, MTA and 5′dAdo, similar to the action of bacterial SAH/MTA nucleosidases. We also found that the binding of SAM or SAH causes a significant change in the structure of WBSCR27 and in the conformational mobility of the protein fragments, which can be attributed to the substrate recognition site. This indicates that the binding of the cofactor modulates the folding of the substrate-recognizing region of the enzyme.

A three-acetyl deoxyribose α isomer preparation method

The invention discloses a capecitabine intermediate impurity tri acetyl deoxyribose α isomer: the chemical name is 1 α - 1, 2, 3 - three-acetoxy - 5 - deoxy - D - ribose of the preparation method. The preparation method in order to 5 - deoxy - D - ribose as a synthetic raw material, by isopropenyl acetate/iron trichloride acetylation than three acetyl deoxyribose α isomer crude, passes through the column again chromatography purification to obtain the triacetyl deoxyribose α isomer pure product. The invention provides a triacetyl deoxyribose α isomer preparation method, with simple operation, the advantage of the high product purity, for capecitabine intermediate and the quality of the finished good foundation for the study.

Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism

Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.