37077-81-9

Usage

Uses

Used in Organic Chemistry:
1,2-O-(1-methylethylidene)-alpha-D-ribofuranose is used as a key intermediate for the synthesis of complex organic compounds due to its unique reactivity and structural features.
Used in Pharmaceutical Research:
1,2-O-(1-methylethylidene)-alpha-D-ribofuranose is used as a building block for the development of new drugs and bioactive molecules, leveraging its unique chemical properties to create novel therapeutic agents.
Used in Drug Synthesis:
In the pharmaceutical industry, 1,2-O-(1-methylethylidene)-alpha-D-ribofuranose is utilized as a starting material for the synthesis of various pharmaceutical compounds, contributing to the discovery and production of innovative medications.
Overall, 1,2-O-(1-methylethylidene)-alpha-D-ribofuranose is a versatile and significant chemical compound that plays a crucial role in advancing both organic chemistry and pharmaceutical research, facilitating the creation of new and effective drugs and other chemical entities.

Upstream product

• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 63846-98-0 1,2-O-(1-Methylethylidene)-α-D-ribo-pentodialdo-1,4-furanose 
• 6612-91-5 ((3aR,5R,65,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate 
• 532-20-7 D-xylofuranose 
• 80244-95-7 3,5-di-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose 
• 80244-96-8 5-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 20590-54-9 1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose 
• 20590-57-2 1,2-O-isopropylidene-5-O-trityl-α-D-ribofuranose 
• 20590-53-8 1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose 
• 2280-44-6 D-Glucose 
• 67-64-1 acetone 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 196868-07-2 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-ribofuranoside 
• 85951-12-8 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside 

Downstream Products

• 20590-57-2 1,2-O-isopropylidene-5-O-trityl-α-D-ribofuranose 
• 138679-69-3 1,4-anhydro-3,5-di-O-benzyl-D-ribitol 
• 151825-72-8 (2R)-2-C-(adenin-9-yl)-1,4-anhydro-3,5-di-O-benzyl-2-deoxy-D-arabitol 
• 161452-67-1 (2R)-2-amino-1,4-anhydro-3,5-di-O-benzyl-2-deoxy-D-arabitol 
• 161452-59-1 1,4-anhydro-3,5-di-O-benzyl-2-O-isopropyl-D-ribitol 
• 161452-65-9 (2R)-1,4-anhydro-2-azido-3,5-di-O-benzyl-2-deoxy-D-arabitol 
• 161452-60-4 1,4-anhydro-3,5-di-O-benzyl-2-O-methanesulfonyl-D-ribitol 
• 161452-71-7 (2R)-1,4-anhydro-3,5-di-O-benzyl-2-deoxy-2-C-(uracil-1-yl)-D-arabitol 
• 161452-72-8 (2R)-1,4-anhydro-3,5-di-O-benzyl-2-C-(cytosin-1-yl)-2-deoxy-D-arabitol 
• 161452-69-3 (2R)-1,4-anhydro-3,5-di-O-benzyl-2-deoxy-2--D-arabitol 
• 161452-62-6 (2R)-1,4-anhydro-3,5-di-O-benzyl-2-C-(2,6-diaminopurin-9-yl)-2-deoxy-D-arabitol 
• 131139-05-4 3,5-di-O-benzyl-D-ribo-penta-1,4-lactone 
• 131139-13-4 methyl 2,4-anhydro-3,5-di-O-benzyl-D-ribonate 
• 131139-09-8 3,5-di-O-benzyl-D-ribono-1,4-lactone-2-O-trifluoromethanesulphonate 

Relevant academic research and scientific papers

Reaction of acetylated carbohydrates with trimethylaluminum: concise synthesis of 1,2-O-isopropylidene d-ribofuranose

Treatment of β-d-ribose tetraacetate with trimethylaluminum gives α-3,5-O-acetyl-1,2-O-isopropylidene-d-ribofuranoside in excellent yield. This reaction allows for efficient and high-yielding installation of the 1,2-isopropylidene acetal (acetonide), whic

Development of 2-Deoxy-2-[18F]fluororibose for Positron Emission Tomography Imaging Liver Function in Vivo

Life-threatening acute liver failure can be triggered by a variety of factors, including common drugs such as acetaminophen. Positron emission tomography (PET) is rarely used to monitor liver function, in part because of a lack of specific imaging agents for liver function. Here we report a new PET probe, 2-deoxy-2-[18F]fluororibose ([18F]-2-DFR), for use in imaging liver function. [18F]-2-DFR was synthesized and validated as a competitive substrate for the ribose salvage pathway. [18F]-2-DFR was prepared through an efficient late stage radiofluorination. The desired selectivity of fluorination was achieved using an unorthodox protecting group on the precursor, which could withstand harsh SN2 reaction conditions with no side reactions. [18F]-2-DFR accumulated preferentially in the liver and was metabolized by the same enzymes as ribose. [18F]-2-DFR could distinguish between healthy liver and liver damaged by acetaminophen. [18F]-2-DFR is expected to be a useful PET probe for imaging and quantifying liver functions in vivo, with likely significant clinical utility.

Synthesis and evaluation of 3′-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents

Kinetoplastid parasites are the causative agents of neglected tropical diseases with an unmet medical need. These parasites are unable to synthesize the purine ring de novo, and therefore rely on purine salvage to meet their purine demand. Evaluating purine nucleoside analogs is therefore an attractive strategy to identify antikinetoplastid agents. Several anti-Trypanosoma cruzi and anti-Trypanosoma brucei 7-deazapurine nucleosides were previously discovered, with the removal of the 3′-hydroxyl group resulting in a significant boost in activity. In this work we therefore decided to assess the effect of the introduction of a 3′-fluoro substituent in 7-deazapurine nucleosides on the anti-kinetoplastid activities. Hence, we synthesized two series of 3′-deoxy-3′-fluororibofuranosyl and 3′-deoxy-3′-fluoroxylofuranosyl nucleosides comprising 7-deazaadenine and -hypoxanthine bases and assayed these for antiparasitic activity. Several analogs with potent activity against T. cruzi and T. brucei were discovered, indicating that a fluorine atom in the 3′-position is a promising modification for the discovery of antiparasitic nucleosides.

NOVEL SPIROBICYCLIC INTERMEDIATES

The present invention relates to novel spirobicyclic intermediates useful in the synthesis of spirobicyclic nucleoside analogues.

Total synthesis of mycalisine B

The first total synthesis of the marine nucleoside Mycalisine B-a naturally occurring and structurally distinct 4,5-unsaturated 7-deazapurine nucleoside-has been accomplished in 10 linear steps with 27.5% overall yield from commercially available 1,2,3,5-tetra-O-acetyl-ribose and tetracyanoethylene. Key steps of the approach include: (1) I2 catalyzed acetonide formation from 1,2,3,5-tetra-O-acetylribose and acetone at large scale; (2) Vorbrüggen glycosylation using N4-benzoyl-5-cyano-6-bromo-7H-pyrrolo[2,3-d]pyrimidine as a nucleobase to avoid formation of N-3 isomer; (3) mild and scalable reaction conditions.

Larger laboratory scale synthesis of 5-methyluridine and formal synthesis of its L-enantiomer

A larger laboratory scale synthesis (>60 g per run) of 5-methyluridine is presented. The critical intermediate 1,2-O-isopropylidene-α-D-ribofuranose was prepared from very cheap D-glucose via D-allose. Its L-enantiomer was obtained from L-arabinose via L-glucose, and also from L-xylose. {figure presented}.

Prebiotic synthesis of aminooxazoline-5′-phosphates in water by oxidative phosphorylation

RNA is essential to all life on Earth and is the leading candidate for the first biopolymer of life. Aminooxazolines have recently emerged as key prebiotic ribonucleotide precursors, and here we develop a novel strategy for aminooxazoline-5′-phosphate synthesis in water from prebiotic feedstocks. Oxidation of acrolein delivers glycidaldehyde (90%), which directs a regioselective phosphorylation in water and specifically affords 5′-phosphorylated nucleotide precursors in upto 36% yield. We also demonstrated a generational link between proteinogenic amino acids (Met, Glu, Gln) and nucleotide synthesis.

The convergent synthesis and anticancer activity of broussonetinines related analogues

The convergent synthesis of broussonetinines related congeners 3 and 4 with the simple C13 alkyl side chain and differently configured pyrrolidine skeleton has been achieved. Our approach relied on the [3,3]-sigmatropic rearrangements of chiral allylic substrates derived from D-xylose. Cross metathesis of the common oxazolidinone intermediates 7 and 8 with tridec-1-ene followed by alkylative cyclization completed the construction of both C-alkyl iminosugars. The targeted compounds 3 and 4 were screened for antiproliferative/cytotoxic activities against multiple cancer cell lines by MTT assay. Compound 3 exhibited very good in vitro potency on Caco-2 and Jurkat cell lines with IC50 value of 5.1 μM and 5.8 μM, respectively.

NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

First total synthesis of kipukasin A

In this paper, a practical approach for the total synthesis of kipukasin A is presented with 22% overall yield by using tetra-O-acetyl-β-D-ribose as starting material. An improved iodine-promoted acetonide-forming reaction was developed to access 1,2-O-is