149623-91-6 Usage
Derivative of ribofuranoside
Type of sugar molecule
The compound is derived from a specific type of sugar molecule.
β-D-ribofuranoside
Specific form of the sugar molecule
The compound is in the form of β-D-ribofuranoside.
Two fluoro substituents
Presence of fluorine atoms
The compound has two fluorine atoms attached to the sugar ring.
Acetyl and benzoyl groups
Attached functional groups
The compound has acetyl and benzoyl groups attached to the sugar ring.
Medicinal chemistry and drug development
Field of application
The compound is useful in creating other chemical entities for various applications in medicinal chemistry and drug development.
Starting material
Role in creating other chemical entities
1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranoside can be used as a starting material for synthesizing other compounds.
Sugar chemistry and biochemistry
Fields of study
The compound's specific structure and properties make it valuable for studies in sugar chemistry and biochemistry.
Interest to researchers
Organic, medicinal, and biochemistry fields
Due to its intricate structure and potential applications, the compound is of interest to researchers in organic chemistry, medicinal chemistry, and biochemistry.
Check Digit Verification of cas no
The CAS Registry Mumber 149623-91-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,9,6,2 and 3 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 149623-91:
(8*1)+(7*4)+(6*9)+(5*6)+(4*2)+(3*3)+(2*9)+(1*1)=156
156 % 10 = 6
So 149623-91-6 is a valid CAS Registry Number.
149623-91-6Relevant articles and documents
Oxidation-reduction sequence for the synthesis of peracylated fluorodeoxy pentofuranosides
Mikhailopulo, Igor A.,Sivets, Grigorii G.,Poopeiko, Nicolai E.,Khripach, Natalia B.
, p. 71 - 90 (2007/10/03)
The oxidation of methyl 5-O-benzyl-3(2)-deoxy-3(2)-fluoro-α-D-pentofuranosides with dimethyl sulfoxide-acetic (trifluoroacetic) anhydride was accompanied by epimerization at the carbon atom bearing a fluoro function, resulting in the formation of the corresponding 2- or 3-keto derivatives as mixtures of two epimers in high combined yield.Reduction of a mixture of the erythro/threo epimeric 2-keto sugars (isolated as stable hydrates) with sodium borohydride in benzene-ethanol proceeded stereoselectively leading to the formation of 3-deoxy-3-fluoro ribo- and lyxo-furanosides, respectively.In the case of the ribo and arabino epimers of the 3-keto sugar (isolated as free ketones), reduction stereoselectivity of the former was >95percent for the 2-deoxy-2-fluoro ribo sugar, whereas a ca. 3:1 lyxo/arabino ratio of products was obtained for the latter.Treatment of a mixture of the 2-epimeric 3-keto sugars with triethylamine in carbon tetrachloride at room temperature for 3-5 h afforded the 2-deoxy-2-fluoro ribo ketone (ca. 90percent).The synthesis of 1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3-fluoro-α,β-D-lyxofuranose (8) and 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-2-fluoeo-β-D-ribofuranose (16) and their use as glycosylating agents for bis-trimethylsilylated N6-benzoyladenine is described.Keywords: Fluorodeoxy pentafuranosides; Keto sugars; Epimerization
