64363-77-5

Usage

Uses

Used in Organic Synthesis:
Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside is used as a protective group in organic synthesis for the hydroxyl groups of ribofuranoside sugar molecules. The benzyl groups provide a stable and easily removable protection, facilitating selective reactions and modifications of the sugar moiety.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside is utilized as a key intermediate for the modification of nucleosides and nucleotides. The protective benzyl groups enable chemists to perform specific chemical transformations on the sugar component without affecting the rest of the molecule, which is crucial for the development of novel bioactive compounds and pharmaceuticals.
Used in the Synthesis of Bioactive Compounds:
Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside serves as an important building block in the synthesis of various bioactive compounds. Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside's unique structure and protective benzyl groups allow for the creation of diverse molecules with potential therapeutic properties, contributing to the discovery of new drugs and treatments.
Used in Pharmaceutical Development:
In the pharmaceutical industry, Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside is employed as a crucial component in the development of new drugs. Its role in the synthesis of nucleoside and nucleotide analogs makes it a valuable asset in the creation of antiviral, anticancer, and other therapeutic agents. The selective protection and manipulation of the sugar moiety provided by the benzyl groups ensure the production of effective and targeted pharmaceuticals.

Upstream product

• 67-56-1 methanol 
• 86883-42-3 2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranosyl fluoride 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 
• 96-36-6 methyl phosphite 
• 1825-61-2 Trimethylmethoxysilane 
• 67737-48-8 methyl 5-benzyloxy-β-D-ribofuranoside 
• 100-44-7 benzyl chloride 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 191543-71-2 methyl 3,5-di-O-benzyl-α-D-ribofuranoside 
• 86883-41-2 2,3,5-tri-O-benzyl-α-D-ribofuranosyl fluoride 
• 1824-96-0 methyl ribofuranoside 
• 50-69-1 D-ribose 
• 532-20-7 D-Ribose 

Downstream Products

• 79083-29-7 (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran 
• 79064-00-9 (2R,3R,4S)-1,3,4-Tris-benzyloxy-5-methoxy-hexan-2-ol 
• 491-19-0 1,4-anhydro-D-ribitol 
• 149118-07-0 (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-phenylsulfanyl-tetrahydro-furan 
• 1330085-36-3 3-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-1-propyne 
• 93836-22-7 4,7-anhydro-5,6,8-tri-O-benzyl-1,2,3-trideoxy-D-altro-oct-1-enitol 
• 88222-69-9 2-Methyl-2-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)propionsaeure-methylester 
• 88222-68-8 2-Methyl-2-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)propionsaeure-methylester 
• 88222-67-7 2-(2,3,5-Tri-O-benzyl-α,β-D-ribofuranosyl)-3-pentanon 
• 88222-65-5 3,3-dimethyl-1-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-2-butanone 
• 88222-65-5 3,3-dimethyl-1-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-2-butanone 
• 98815-79-3 (2R,3R,3aS,9bR)-3-benzyloxy-2-benzyloxymethyl-3,3a,5,9b-tetrahydro-2H-furo<3,2-c><2>benzopyran 
• 84366-59-6 (2S,3R,4R)-2,3,5-tri-O-benzyl-pentane-1,4-diol 
• 80795-53-5 (2S,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxytetrahydrofuran-3-ol 

Relevant academic research and scientific papers

Chemical synthesis of linear ADP-ribose oligomers up to pentamer and their binding to the oncogenic helicase ALC1

ADP-ribosylation is a pivotal post-translational modification that mediates various important cellular processes producing negatively charged biopolymer, poly (ADP-ribose), the functions of which need further elucidation. Toward this end, the availability

ANTIVIRAL NUCLEOSIDES AND DERIVATIVES THEREOF

Disclosed herein are nucleoside compounds and derivatives thereof, pharmaceutical compositions containing same, and their methods of synthesis. The compounds are useful in treating orthomyxovirus infections, such as influenza infections.

Synthesis of remdesivir key intermediate 2, 3, 5-tribenzyloxy-D-ribotide-1, 4-lactone

The invention relates to synthesis of a remdesivir key intermediate 2, 3, 5-tribenzyloxy-D-ribotide-1, 4-lactone. The invention discloses a synthesis method of 2, 3, 5-tribenzyloxy-D-ribotide-1, 4-lactone, and belongs to the field of organic synthesis. The method includes: taking D-ribose as an initial raw material, in methanol, using concentrated sulfuric acid as a catalyst, synthesizing a methoxy compound 2, then fully stirring the substances in a saturated sodium hydroxide solution, adding tetrahydrofuran and n-butylammonium hydrogen sulfate, and then adding benzyl bromide to synthesize a compound 3, dissolving the compound 3 in tetrahydrofuran and then performing catalysis with concentrated sulfuric acid, and performing reflux stirring overnight treatment to obtain a compound 4, dissolving the compound 4 into dichloromethane and water, adding sodium bicarbonate and TEMPO, slowly adding sodium hypochlorite at 0DEG C, raising the temperature to room temperature, and conducting stirring overnight treatment to obtain a compound 5. The method has the characteristics of easily available raw materials and low production cost, each process step is simple and easy to treat, the yield ofthe whole route reaches 43% or above, industrial production is easy to realize, and a basis is provided for industrialization of remdesivir and subsequent derivatives thereof.

COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USE THEREOF AS INHIBITORS OF RAN GTPASE

Compounds of general formula IA, IB and IC outlined below, including pharmaceutically acceptable salts, solvates and hydrates thereof. Such compounds and pharmaceutical compositions comprising them may be used in medical conditions involving Ran GTPase.

Synthesis, Reactivity, and Stereoselectivity of 4-Thiofuranosides

Thiosugars, sugars that have their endocyclic oxygen substituted for a sulfur atom, have been used as stable bioisosteres of naturally occurring glycans because the thiosugar glycosydic linkage is supposed to be stabilized toward chemical and enzymatic hydrolysis. We have performed an in-depth investigation into the stability and reactivity of furanosyl thiacarbenium ions, by assessing all four diastereoisomeric thiofuranosides experimentally and computationally. We show that all furanosyl thiacarbenium ions react in a 1,2-cis-selective manner with triethylsilane, reminiscent of their oxo counterparts. The computed conformational space occupied by the thiacarbenium ions is strikingly similar to that of the corresponding furanosyl oxycarbenium ions, indicating that the stereoelectronic substituent effects governing the stability of furanosyl oxocarbenium ions and thiacarbenium ions are very similar. While the thio-ribo-furanose appears to be less reactive than its oxo counterpart, the thio-ara-, lyxo-, and xylo-furanosides appear to be more reactive than their oxygen equivalents. These differences are accounted for using the conformational preference of the donors and the carbocation intermediates. The lower reactivity of the thio-ribo furanosides in (Lewis) acid-mediated reactions and the similarity of the thia- and oxocarbenium ions make thio-ribo-furanosides excellent stabilized analogues of the naturally occurring ribo-furanose sugars.

Computer Modelling and Synthesis of Deoxy and Monohydroxy Analogues of a Ribitylaminouracil Bacterial Metabolite that Potently Activates Human T Cells

5-(2-Oxopropylideneamino)-6-d-ribitylaminouracil (5-OP-RU) is a natural product formed during bacterial synthesis of vitamin B2. It potently activates mucosal associated invariant T (MAIT) cells and has immunomodulatory, inflammatory, and anticancer properties. This highly polar and unstable compound forms a remarkably stable Schiff base with a lysine residue in major histocompatibility complex class I–related protein (MR1) expressed in antigen-presenting cells. Inspired by the importance of the ribityl moiety of 5-OP-RU for binding to both MR1 and the T cell receptor (TCR) on MAIT cells, each OH was removed in silico. DFT calculations and MD simulations revealed a very stable hydrogen bond between the C3′?OH and uracil N1H, which profoundly restricts flexibility and positioning of each ribityl-OH, potentially impacting their interactions with MR1 and TCR. By using deoxygenation strategies and kinetically controlled imine formation, four monodeoxyribityl and four monohydroxyalkyl analogues of 5-OP-RU were synthesised as new tools for probing T cell activation mechanisms.

Synthetic process for benzyl ribose lactone

The invention discloses a synthetic process for benzyl ribose lactone, relates to the technical field of medicine synthesis, and solves the technical problems that crystal purification steps in an existing process are complex, and reaction still locking can appear. According to the process, different reagent and solvent are selected, intermediate does not undergo the purification treatment and directly gets into the next step with an oily matter or without further concentration treatment, the intermediate undergoes separation and purification and crystallization at the final step, the processhas the advantages that the purification and crystallization steps are simple, and the problem of the reaction still locking can not appear, the loss is reduced, the yield coefficient reaches to 79%,and the purity reaches to 99% or above; According to the process, the expensive solvent is replaced by the cheap reagent, under the circumstance of not affecting the product quality and yield coefficient, the synthesis cost of the benzyl ribose lactone is reduced.

COMPOSITION COMPRISING PAEONIFLORIN OR ALBIFLORIN ANALOGUE, METHOD OF PREPARATION THEREOF

A composition comprises a compound of formula (I) and at least one cosmetically acceptable carrier. It can be used for preventing or decreasing skin pigmentation and /or lightening skin tone.

SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF

Disclosed herein are nucleotide analogs, methods of synthesizing nucleotide analogs and methods of treating diseases and/or conditions such as a Picornaviridae and/or Flaviviridae viral infections with one or more nucleotide analogs.

A process for preparing β - dione carbon of nucleosides (by machine translation)

The invention discloses a process for preparing carbon of nucleosides: using different head position hydroxy exposed sugar 1 with the acetylenic ketone 2 Michael addition reaction occurs, then the addition product 3 then under Lewis acid catalysis, throug