51255-17-5

Basic information

• Product Name: Methyl-2-deoxy-alpha-D-ribofuranoside
• Synonyms: ALPHA-D-ERYTHRO-PENTOFURANOSIDE;METHYL 2-DEOXY-D-RIBOSIDE;METHYL-2-DEOXY-ALPHA-D-RIBOFURANOSIDE;Methyl-2-deoxy-alpha-D-ribofur;A-D-ERYTHRO-PENTOFURANOSIDE;Methyl 2-deoxy-a-D-ribofuranoside
• CAS NO: 51255-17-5
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.16
• Mol File: 51255-17-5.mol
• Article Data: 87

Chemical Properties

• Boiling Point: 294.5±40.0 °C(Predicted)
• Appearance: /
• Density: 1.24 g/cm³
• Refractive Index: 1.487
• PKA: 13.81±0.60(Predicted)
• CAS DataBase Reference: Methyl-2-deoxy-alpha-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-2-deoxy-alpha-D-ribofuranoside(51255-17-5)
• EPA Substance Registry System: Methyl-2-deoxy-alpha-D-ribofuranoside(51255-17-5)

Safety Data

• Hazardous Substances Data: 51255-17-5(Hazardous Substances Data)

Usage

General Description

Methyl-2-deoxy-alpha-D-ribofuranoside is a chemical compound that is commonly used in the pharmaceutical industry as a building block for the synthesis of nucleoside analogs and other biologically active molecules. It is a modified form of the sugar ribose, with a methyl group replacing the hydroxyl group at the 2' position. This modification allows the compound to be more stable and resistant to degradation, making it useful for the development of new drugs. Methyl-2-deoxy-alpha-D-ribofuranoside is also used in research and development as a reference compound for the study of nucleoside metabolism and as a standard for quantification in analytical chemistry.

InChI:InChI=1/C6H11O4/c1-9-4-2-6(8)10-5(4)3-7/h4-7H,2-3H2,1H3/q-1/t4-,5+,6-/m0/s1

Upstream product

• 67-56-1 methanol 
• 22900-10-3 2-deoxy-D-ribose 
• 79364-36-6 (2R,3S)-hex-5-ene-1,2,3-triol 
• 452-51-7 D-2-deoxyribose 
• 131451-60-0 (1R,2R,4aS,5S,8aR)-2-(2-Hydroxy-ethyl)-5-methoxymethoxy-1-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 36792-88-8 2-deoxy-D-ribose 
• 533-67-5 2-Deoxy-D-ribose 
• 533-67-5 2-deoxy-D-ribose 
• 128161-77-3 (2S,3R)-2-<2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybut-1-yl>-1,3-dithiane 
• 103795-36-4 (3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal 
• 128111-92-2 (2S,3R)-2-<3,4-O-isopropylidene-2,3,4-trihydroxybut-1-yl>-1,3-dithiane 
• 862776-19-0 Acetic acid (2R,3R,4S,5S)-2-acetoxymethyl-4-(imidazole-1-carbothioyloxy)-5-methoxy-tetrahydro-furan-3-yl ester 
• 682811-40-1 methyl 3,5-di-O-acetyl-α-D-arabinofuranoside 
• 23701-40-8 methyl 3,5-di-O-acetyl-2-deoxy-α-D-ribofuranoside 

Downstream Products

• 60110-69-2 methyl 2-deoxy-3,5-di-O-p-toluenesulfonyl-D-erythro-pentofuranoside 
• 17676-20-9 methyl 2-deoxy-β-D-erythro-pentopyranoside 
• 151767-35-0 3,5-di-O-acetyl-2-deoxy-α/β-D-ribofuranoside 
• 132487-16-2 methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside 
• 6160-55-0 methyl 3,5-di-O-benzyl-2-deoxy-β-D-erythro-pentofuranoside 
• 6160-54-9 methyl 3,5-di-O-benzyl-2-deoxy-α-D-erythro-pentofuranoside 
• 108647-88-7 ((2R,3S)-3-(benzoyloxy)-5-methoxytetrahydrofuran-2-yl)methyl benzoate 
• 51785-70-7 methyl 3,5-dibenzoyloxy-2-deoxy-β-D-erythropentofuranoside 
• 80339-59-9 methyl 3,5-dibenzoyloxy-2-deoxy-α-D-erythropentofuranoside 
• 144071-99-8 1-methyl-5-O-benzoyl-2-deoxy-α-D-ribofuranoside 
• 144072-00-4 1-methyl-5-O-benzoyl-2-deoxy-β-D-ribofuranoside 
• 4330-34-1 methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose 
• 676598-19-9 methyl 2-deoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside 
• 10437-39-5 methyl 2-deoxy-5-O-(p-toluenesulfonyl)-α,β-D-erythro-pentofuranoside 

Relevant articles and documents

Preparation method of decitabine intermediate

The invention belongs to the field of pharmaceutical synthesis, and discloses a preparation method and a purification method of a decitabine intermediate (V). The preparation method comprises the following steps of enabling 2-deoxygenation-D-ribose derivative (III) and hexamethyldisilazane-activated 5-azacytosine (IV) to be subjected to a coupling reaction under the action of a catalyst to be purified to obtain the decitabine intermediate (V). The method is simple and convenient to operate, no silica gel column purification product is needed, and the method is suitable for industrial production.

2-deoxy-D-ribose derivative

The invention belongs to the field of medicine synthesis, and provides a 2-deoxy-D-ribose derivative (III). When the derivative (III) is used for preparing decitabine, the stereoselectivity is good, and the yield is high. The invention provides a preparation method of the derivative. The preparation method comprises the following steps: step a, carrying out oxygen methylation on 1-position hydroxyl of 2-deoxy-D-ribose; and step b, protecting hydroxyl groups at positions 3 and 5, and further carrying out sulfonation on 1-position oxymethyl. The method is simple and convenient to operate, free of special equipment, good in product purity, high in yield and suitable for industrial production.

The development of β-selective glycosylation reactions with benzyl substituted 2-deoxy-1,4-dithio-D-erythro-pentofuranosides: enabling practical multi-gram syntheses of 4'-Thio-2'-deoxycytidine (T-dCyd) and 5-aza-4’-thio-2’-deoxycytidine (aza-T-dCyd) to s

The lack of effective methods to perform direct β-selective glycosylation reactions with 2-deoxy-1,4-dithio-D-erythro-pentofuranosides has long been a significant stumbling block for the multi-gram synthesis of 4’-thio-2’-deoxy nucleosides. In addition, p