60134-26-1

Basic information

• Product Name: 1-O-Methyl-2-deoxy-D-ribose
• Synonyms: 1-O-METHYL-2-DEOXY-D-RIBOSE;METHYL 2-DEOXY-D-RIBOSE;1-O-METHYL 2-DEOXY-D-RIBOSE (2R,3S)-2-(HYDROXYMETHYL)-5-METHOXYTETRAHYDROFURAN-3-OL;(2R,3S)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3-ol;Methyl 2-Deoxyribofuranoside;(2S,3R)-2-(hydroxyMethyl)-5-Methoxyoxolan-3-ol;D-Ribofuranoside,Methyl 2-deoxy- (6CI);1-Methoxy-2-deoxyribose
• CAS NO: 60134-26-1
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 149.17
• EINECS: 1533716-785-6
• Product Categories: Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis;Carbohydrates & Derivatives
• Mol File: 60134-26-1.mol
• Article Data: 79

Chemical Properties

• Boiling Point: 294.492 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: Golden gummy solid
• Density: 1.224 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.47(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 13.81±0.60(Predicted)
• CAS DataBase Reference: 1-O-Methyl-2-deoxy-D-ribose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-Methyl-2-deoxy-D-ribose(60134-26-1)
• EPA Substance Registry System: 1-O-Methyl-2-deoxy-D-ribose(60134-26-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 60134-26-1(Hazardous Substances Data)

Usage

Description

1-O-METHYL-2-DEOXY-D-RIBOSE, also known as Methyl 2-Deoxy-D-ribofuranoside (CAS# 60134-26-1), is a chemical compound derived from the sugar molecule deoxyribose. It is characterized by a golden gummy solid appearance and is primarily used in organic synthesis due to its unique chemical properties.

Uses

Used in Organic Synthesis:
1-O-METHYL-2-DEOXY-D-RIBOSE is used as a synthetic building block for the creation of various complex organic molecules. Its unique structure allows it to be a valuable component in the synthesis of a wide range of compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
1-O-METHYL-2-DEOXY-D-RIBOSE is used as a key intermediate in the development of new drugs, particularly in the design and synthesis of novel antiviral, anticancer, and antimicrobial agents. Its unique chemical properties enable the creation of innovative drug candidates with potential therapeutic applications.
Used in Research and Development:
1-O-METHYL-2-DEOXY-D-RIBOSE is utilized as a research tool in the study of various biological processes and the development of new methodologies in organic chemistry. Its unique structure and reactivity make it an important compound for exploring new reaction pathways and understanding the fundamental principles of chemical synthesis.

InChI:InChI=1/C6H12O4/c1-9-6-2-4(8)5(3-7)10-6/h4-8H,2-3H2,1H3/t4-,5+,6?/m0/s1

Upstream product

• 67-56-1 methanol 
• 22900-10-3 2-deoxy-D-ribose 
• 533-67-5 2-Deoxy-D-ribose 
• 452-51-7 D-2-deoxyribose 
• 75-36-5 acetyl chloride 
• 533-67-5 2-deoxy-D-ribose 
• 137873-06-4 2,5,6-trideoxy-D-erythro-hexofuranose 
• 22900-10-3 2-deoxy-β-D-erythro-pentopyranose 
• 36792-88-8 2-deoxy-D-ribose 
• 77909-74-1 2,5-anhydro-3-deoxy-D-ribo-hexonic acid 
• 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 
• 79364-36-6 (2R,3S)-hex-5-ene-1,2,3-triol 
• 91547-59-0 (2R,3S)-2-(hydroxymethyl)tetrahydrofuran-3-ol 

Downstream Products

• 51785-70-7 methyl 3,5-dibenzoyloxy-2-deoxy-β-D-erythropentofuranoside 
• 80339-59-9 methyl 3,5-dibenzoyloxy-2-deoxy-α-D-erythropentofuranoside 
• 17676-20-9 methyl 2-deoxy-β-D-erythro-pentopyranoside 
• 452-51-7 D-2-deoxyribose 
• 105454-47-5 methyl 2-deoxy-5-O-(4-methoxyphenyl)diphenyl-D-methyl-erythro-pento-D-furanoside 
• 148903-86-0 tert-butyl(((2R,3S)-3-((tert-butyldiphenylsilyl)oxy)-5-methoxytetrahydrofuran-2-yl)methoxy)diphenylsilane 
• 127306-47-2 methyl-5-O-tert-butyldiphenylsilyl-2-deoxy-ribo-furanoside 
• 130144-85-3 (2R,3S,5S)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5α-methoxytetrahydrofuran 
• 130144-86-4 (2R,3S,5R)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5β-methoxytetrahydrofuran 
• 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 
• 60110-69-2 methyl 2-deoxy-3,5-di-O-p-toluenesulfonyl-D-erythro-pentofuranoside 
• 60251-58-3 methyl 2-deoxy-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranoside 
• 10437-39-5 methyl 2-deoxy-5-O-(p-toluenesulfonyl)-α,β-D-erythro-pentofuranoside 

Relevant articles and documents

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

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.

Open-Close Strategy toward the Organocatalytic Generation of 2-Deoxyribosyl Oxocarbenium Ions: Pyrrolidine-Salt-Catalyzed Synthesis of 2-Deoxyribofuranosides

The reaction of secondary amine salts with 2-deoxy-ribofuranoses under forcible conditions leads to the putative furanosyl oxocarbenium ion that is trapped with various alcohols to provide 2-deoxy-ribofuranosides. The observed anomeric selectivities range from an equimolar mixture to complete α-selectivity in the case of bulky sugar acceptors. Owing to the mechanism and temperature of the transformation, the generated oxocarbenium ion shows little or no facial preference towards the nucleophilic attack of non-carbohydrate acceptors and leads to a mixture of anomers in the case of benzyl and acetyl protected donors. However, the conformationally less flexible tetraisopropylsilyl protected donor reacted with both sugar and non-sugar acceptors in a stereoselective fashion. Besides, the glycosylation with 2-cyanoethanol gave the product with unexpected beta-selectivity presumably due to nitrile effect. The operationally simple organocatalytic protocol provides easy access to otherwise difficult 2-deoxy-ribofuranosides/disaccharides.