55735-86-9

Usage

Uses

Used in Organic Synthesis:
α-D-Ribofuranose, 1,2-O-(1-methylethylidene)-3,5-bis-O-(phenylmethyl)is used as a building block in organic synthesis for the development of novel molecules with potential therapeutic applications. Its unique chemical reactivity and structural modifications make it a valuable component in the synthesis of complex organic compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, α-D-Ribofuranose, 1,2-O-(1-methylethylidene)-3,5-bis-O-(phenylmethyl)is used as a key component in the research and development of new drugs. Its potential biological activities and medicinal properties make it a promising candidate for the treatment of various diseases and conditions. Researchers utilize its enhanced stability and unique chemical reactivity to design and synthesize innovative pharmaceutical compounds with improved efficacy and safety profiles.
Used in Drug Development:
α-D-Ribofuranose, 1,2-O-(1-methylethylidene)-3,5-bis-O-(phenylmethyl)is employed in drug development as a starting material or intermediate in the synthesis of pharmaceutical compounds. Its unique structural features and chemical properties allow for the creation of new drug candidates with potential therapeutic benefits. α-D-Ribofuranose, 1,2-O-(1-methylethylidene)-3,5-bis-
O-(phenylmethyl)-'s versatility in organic synthesis and its potential to be modified further make it an attractive option for the development of novel drugs with improved pharmacological properties.

Upstream product

• 2592-42-9 5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose 
• 100-39-0 benzyl bromide 
• 114861-14-2 1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 6698-46-0 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose 
• 6022-96-4 5-O-benzoyl-α-D-xylofuranose 
• 37077-82-0 ((3aR,5R,6R,6aR)-6-acetoxy-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methyl acetate 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 37077-81-9 1,2-isopropylidene-α-D-ribofuranose 
• 100-44-7 benzyl chloride 
• 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 
• 103931-45-9 5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose 

Downstream Products

• 16054-77-6 (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol 
• 561055-45-6 (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol 
• 55775-39-8 1-O-methyl-3,5-di-O-benzyl-D-ribofuranoside 
• 138679-69-3 1,4-anhydro-3,5-di-O-benzyl-D-ribitol 
• 161452-59-1 1,4-anhydro-3,5-di-O-benzyl-2-O-isopropyl-D-ribitol 
• 16054-78-7 (2S,3S,4R)-3,5-O-dibenzyloxy-1,2,4-pentanetriol 
• 765942-29-8 (2S,3S,4R)-3,5-O-dibenzyloxy-1,2,4-O-tri-tert-butyldimethylsilyloxypentane 
• 765942-31-2 (2R,3R,4S)-1-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-pentan-3-ol 
• 544429-08-5 (2R,3R)-3-hydroxy-2,3-bis(benzylyloxy)propionaldehyde 
• 561055-46-7 (2S,3R)-2,4-bis(benzyloxy)butane-1,3-diol 
• 561055-47-8 (2R,3S)-1,3-Bis-benzyloxy-4-octyloxy-butan-2-ol 
• 561055-48-9 (2R,3S)-1,3-Bis-benzyloxy-4-dodecyloxy-butan-2-ol 
• 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 

Relevant academic research and scientific papers

Synthesis of benzimidazole nucleosides and their anticancer activity

An efficient route for the synthesis of benzimidazole nucleosides 1–8 from readily available D-glucose via 3,5-dihydroxy-1,2-O-isopropylidene-α-D-ribofuranose and 3-azido-3-deoxy-1,2-O-isopropylidene-α-D-xylofuranose intermediates has been adopted. Ribofuranosyl nucleosides 1–4 with different benzimidazole bases, and 3?-deoxy-3?-azido-ribofuranosyl nucleosides 5–8, as another series, were obtained. All these newly synthesized analogs were evaluated for anticancer activity using MDA-MB-231 cell line. Among the differently substituted derivatives, 3?-azide substituted nucleosides (5–8) are more potent compared to ribofuranosyl analogs 1–4. The C-3?-azido analog 8 having anthryl group at 2-position of nucleobase show almost similar potency as that of standard etoposide.

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.

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.

NUCLEOTIDE AND NUCLEOSIDE 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.

Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities

A concise synthesis of (-)-steviamine is reported along with the synthesis of its analogues 10-nor-steviamine, 10-nor-ent-steviamine and 5-epi-ent-steviamine. These compounds were tested against twelve glycosidases (at 143 μg mL-1 concentrations) and were found to have in general poor inhibitory activity against most enzymes. The 10-nor analogues however, showed 50-54% inhibition of α-l-rhamnosidase from Penicillium decumbens while one of these, 10-nor-steviamine, showed 51% inhibition of N-acetyl-β-d-glucosaminidase (from Jack bean) at the same concentration (760 μM). This journal is The Royal Society of Chemistry 2013.

Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor. Part 2

To examine the role of the side chain of kotalanol (2), a potent natural α-glucosidase inhibitor isolated from Salacia reticulata, on inhibitory activity, four diastereomers (11a-11d) with reversed configuration (S) at the C-4′ position in the side chain were synthesized and evaluated. Two of the four (11b and 11d) significantly lost their inhibitory activity against both maltase and sucrase, while the other two (11a and 11c) sustained the inhibitory activity to a considerable extent, showing distinct activity in response to the change of stereochemistry of the hydroxyls at the 5′and 6′ positions. Different activities were rationalized with reference to in silico docking studies on these inhibitors with hNtMGAM. Against isomaltase, all four analogs showed potent inhibitory activity as well as 2, and 11b and 11d exhibited enzyme selectivity.

Specific biotinylation of IMP dehydrogenase

IMP dehydrogenase (IMPDH) catalyzes a critical step in guanine nucleotide biosynthesis. IMPDH also has biological roles that are distinct from its enzymatic function. We report a biotin-linked reagent that selectively labels IMPDH and is released by dithiothreitol. This reagent will be invaluable in elucidating the moonlighting functions of IMPDH.

Synthesis of 3-fluoro-oxetane δ-amino acids

Starting from d-xylose, 2,4-anhydro-5-N-(tert-butoxycarbonyl)amino-5-deoxy- 3-fluoro-d-arabinonic acid 11 was synthesized over 10 steps including ring contraction, fluorination, and ester hydrolysis. Bromine oxidation of d-xylose followed by benzylidenati

O-acetyl-ADP-ribose non-hydrolyzable analogs

Compounds, compositions and methods for modulating cell death in target cells, particularly cancer cells are provided. The compounds are analogs of O-acetyl-ADP-ribose (OAADPr).