cas 64363-77-5, Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside

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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
Filippov, Dmitri V.,Knobloch, Gunnar,Ladurner, Andreas G.,Liu, Qiang,Meeuwenoord, Nico J.,Overkleeft, Herman S.,Voorneveld, Jim,van der Marel, Gijsbert A.
p. 12468 - 12475
(2021)
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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.
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(2020/08/22)

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.
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(2020/07/21)

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.
Madern, Jerre M.,Hansen, Thomas,Van Rijssel, Erwin R.,Kistemaker, Hans A.V.,Van Der Vorm, Stefan,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Filippov, Dmitri V.,Codée, Jeroen D.C.
p. 1218 - 1227
(2019/01/25)

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.
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(2019/04/09)

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.
Ler, Geraldine J. M.,Xu, Weijun,Mak, Jeffrey Y. W.,Liu, Ligong,Bernhardt, Paul V.,Fairlie, David P.
p. 15594 - 15608
(2019/11/16)

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.
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(2018/03/06)

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.
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(2018/04/20)

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.
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(2018/07/30)

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
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Paragraph 0022; 0025-0028

(2018/06/19)

Method for preparing beta-diketone C-nucleoside
The invention provides a method for preparing beta-diketone C-nucleoside. The method utilizes anomeric hydroxyl exposed sugar 1 and beta-diketone 2 to directly generate beta-diketone C-nucleoside compound 3 under the catalysis of Lewis acid, wherein the r
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Paragraph 0018-0024

(2017/06/02)

Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction
Anomeric gem-diallylation, mono-β-crotylation and mono-β- propargylation of sugar 1,5 and 1,4 lactones have been achieved under Barbier reaction conditions using Zn powder and a catalytic amount of TMSCl as an activator. Ring closing olefin metathesis of the synthesized gem-diallyl derivatives furnished C-spiro cyclopentene glycosides. Finally, the cyclopentene rings were converted into carbohydrate based tricyclic morpholine fused triazole glycoconjugates as potential SGLT2 inhibitors.
Lambu, Mallikharjuna Rao,Hussain, Altaf,Sharma, Deepak K.,Yousuf, Syed Khalid,Singh, Baldev,Tripathi, Anil. K.,Mukherjee, Debaraj
p. 11023 - 11028
(2014/03/21)

Uracyl Spirooxetane Nucleoside Phosphoramidates
This invention relates to a stereochemically pure uracyl spirooxetane nucleoside phosphoramidate which inhibits the hepatitis C virus (HCV).
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Paragraph 0042

(2013/09/12)

Uracyl Spirooxetane Nucleoside Phosphoramidates
This invention relates to a stereochemically pure uracyl spirooxetane nucleoside phosphoramidate useful in the treatment of patients infected with the hepatitis C virus (HCV).
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Paragraph 0042

(2013/09/26)

Anodic coupling reactions and the synthesis of C-glycosides
A convenient, two-step procedure has been developed for converting sugar derivatives into C-glycosides containing a masked aldehyde functional group. The chemistry takes advantage of an anodic coupling reaction between an electron-rich olefin and an alcohol. The sequence works for the formation of both furanose and pyranose derivatives if less polarized vinyl sulfide derived radical cation intermediates are used. With more polarized enol ether derived radical cations, the cyclizations work best for the formation of furanose derivatives where the rate of five-membered ring formation precludes elimination reactions triggered by the radical cation.
Xu, Guoxi,Moeller, Kevin D.
supporting information; experimental part
p. 2590 - 2593
(2010/08/22)

Synthesis and properties of triplex-forming oligonucleotides containing 2′-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine
2′-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases.
Lou, Chenguang,Xiao, Qiang,Brennan, Lavinia,Light, Mark E,Vergara-Irigaray, Nuria,Atkinson, Elizabeth M.,Holden-Dye, Lindy M.,Fox, Keith R.,Brown, Tom
experimental part
p. 6389 - 6397
(2010/10/05)

Efficient synthesis of methyl 3,5-di-O-benzyl-α-D-ribofuranoside and application to the synthesis of 2′-C-β-alkoxymethyluridines
Methyl 3,5-di-O-arylmethyl-α-D-ribofuranosides have been used extensively as synthons to construct 2'-C-branched ribonucleosides. Herein, we describe efficient access to methyl 3,5-di-O-arylmethyl-α-D- ribofuranosides (aryl: 2-ClC6H4, 3-ClC6H 4, 4-ClC6H4, 4-BrC6H4, 2,4-Cl2C6H3, Ph) in 72-82% yields from methyl D-ribofuranoside. We also demonstrate efficient access to the versatile precursor methyl 3,5-di-O-benzyl-α-D-ribofuranoside (3f) and the synthesis of 2′-C-β-methoxymethyl- and 2′-C-β-ethoxymethyluridine in six steps from 3f with overall yields of 18% and 32%, respectively.
Li, Nan-Sheng,Lu, Jun,Piccirilli, Joseph A.
p. 3009 - 3012
(2008/02/10)

THERAPEUTIC FUROPYRIMIDINES AND THIENOPYRIMIDINES
The invention provides compounds of formula I, II, and III as described herein, as well as pharmaceutical compositions comprising the compounds, and synthetic methods and intermediates that are useful for preparing the compounds. The compounds of formula I, II, and III are useful as anti-viral agents and/or as anti-cancer agents.
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Page/Page column 57-58

(2008/06/13)

4’-THIONUCLEOSIDES AND OLIGOMERIC COMPOUNDS
The present invention provides modified oligomeric compounds and compositions of oligomeric compounds for use in the RNA interference pathway of gene modulation. The modified oligomeric compounds include siRNA and asRNA having at least one affinity modification.
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Page/Page column 70

(2008/06/13)

Synthesis of β-D-ribofuranosyl-(1→3)-α-L-rhamnopyranose by in situ activating glycosylation using 1-OH sugar derivative and Me3SiBr-CoBr2-Bu4NBr-molecular sieves 4A system
Β-D-Ribofuranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)- L-rhamnopyranose, the trisaccharide repeating unit of the C. freundii O28, 1c O-specific polysaccharide, was synthesized using in situ activating glycosylation of the 1-OH sugar derivatives and a reagent mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and molecular sieves 4A. Regioselective tritylation was useful for synthesizing the 3-OH derivatives of methyl, allyl, and benzyl α-L-rhamnosides.
Hirooka,Mori,Sasaki,Koto,Shinoda,Morinaga
p. 1679 - 1694
(2007/10/03)

C-4' MODIFIED ADENOSINE KINASE INHIBITORS
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(2008/06/13)

Total Syntheses of De-branched Nagstatin and Its Analogs Having Glycosidase Inhibiting Activities
De-branched nagstatin and its analogs have been synthesized from protected L-ribo- and xylo-furanoses through the inter- and intra-molecular nucleophilic reactions with the imidazole moieties.
Tatsuta, Kuniaki,Miura,Shozo,Ohta, Shigeru,Gunji, Hiroki
p. 1085 - 1088
(2007/10/02)

A new synthesis of some 4'-thio-D-ribonucleosides and preliminary enzymatic evaluation
A new synthesis of 4'-thioribonucleosides is presented together with the enzymatic evaluation of the adenosine analogues with respect to adenosine kinase. The 4-thio-D-ribofuranosyl carbohydrate precursor 7 was obtained in good yield from D-ribose and fur
Leydier,Bellon,Barascut,Deydier,Maury,Pelicano,Abdelaziz El Alaoui,Imbach
p. 2035 - 2050
(2007/10/02)

Synthesis of isonucleosides related to AZT and AZU
Approaches to 1,4-anhydro-3-azido-2,3-dideoxy-2-[3,4-dihydro-2,4-dioxo-5- methyl-1(2H)-pyrimidinyl]-D-arabinitol, and the related uracil derivative, have been developed. These conceptually new, optically active analogs of AZT, derived from 1,4-anhydro-D-ribitol, are among the first examples of regioisomeric analogs of AZT.
Purdy,Zintek,Nair
p. 109 - 126
(2007/10/02)

Stereoselective syntheses of α-D- and β-D-ribofuranosides catalyzed by the combined use of silver salts and their partners
α-D-Ribofuranosides are stereoselectively synthesized in high yields from 2,3,5-tri-O-benzyl-1-O-iodoacetyl-D-ribofuranose (1) and trimethylsilylated nucleophiles by the use of silver salts in the coexistence of 3 molar amounts of lithium perchlorate, whi
Shimomura,Mukaiyama
p. 2532 - 2541
(2007/10/02)

C-glycofuranosides via tandem Wittig-Michael sequence using a thiazole-armed phosphorane. A route to C-furanosyl α-hydroxy propanals and propionic acids
The reactions of 2-thiazolylcarbonylmethylenetriphenylphosphorane with five protected D-furanoses (manno, ribo, arabino, xylo, and lyxo) in refluxing toluene lead to mixtures of α- and β-1-C-(2-thiazolacyl)-glycosides (66-93 % overall yield). The β-linked C-glycosides derived from 2,3:5,6-di-O-isopropylidene-D-mannnofuranose was reduced to (R) and (S) akohols which after protection as O-benzyl ethers were transformed to α-alkoxy aldehydes by thiazole-to-formyl conversion; the aldehydes were oxidized to the corresponding α-alkoxy acids.
Dondoni, Alessandro,Marra, Alberto
p. 7327 - 7330
(2007/10/02)

An Efficient Method for the Stereoselective Synthesis of β-D- and α-D-Ribofuranosides from 2,3,5-Tri-O-benzyl-D-ribofuranose by the Use of oxotitanium and Trifluoromethanesulfonic Anhydride
β-D-Ribofuranoside are stereoselectively synthesized in high yields directly from 2,3,5-tri-O-benzyl-D-ribofuranose and trimethylsilylated nucleophiles by the use of oxotitanium and trifluoromethanesulfonic anhydride, while α-D-ribof
Suda, Shinji,Mukaiyama, Teruaki
p. 1211 - 1215
(2007/10/02)

Stereoselective Glycosylation Reaction Starting from 1-O-Trimethylsilyl Sugars by Using Diphenyltin Sulfide and a Catalytic Amount of Active Acidic Species
1,2-trans-Ribofuranosides are stereoselectively synthesized from 1-O-trimethylsilyl ribofuranose and trimethylsilyl ethers in the presence of a catalytic amount of Me3SiOTf using Ph2Sn=S as an additive, while 1,2-cis-ribofuranosides and 1,2-cis-glucopyran
Mukaiyama, Teruaki,Matsubara, Koki
p. 1041 - 1044
(2007/10/02)

Stereoselective Synthesis of 1,2-trans-Ribofuranosides from 1-Hydroxy Sugars by the Use of oxotitanium and Trifluoromethanesulfonic Anhydride
A convenient method for stereoselective synthesis of 1,2-trans-ribofuranosides directly from 1-hydroxy sugars and alcohols or trimethylsilylated nucleophiles by the use of oxotitanium and trifluoromethanesulfonic anhydride is
Suda, Shinji,Mukaiyama, Teruaki
p. 431 - 434
(2007/10/02)

An Efficient Method for the Stereoselective Synthesis of 1,2-cis- and 1,2-trans-Ribofuranosides from 1-Hydroxy Ribofuranose by the Use of Diphenyltin Sulfide and Trifluoromethanesulfonic Anhydride
1,2-trans-Ribofuranosides are stereoselectively synthesized in high yields directly from 1-hydroxy ribofuranose and trimethylsilylated nucleophiles by the use of diphenyltin sulfide and trifluoromethanesulfonic anhydride.Even further, in the coexistence o
Mukaiyama, Teruaki,Matsubara, Koki,Suda, Shinji
p. 981 - 984
(2007/10/02)

ABRAMOW-REAKTION VON KOHLENHYDRATDERIVATEN MIT FREIEN ANOMEREN ZENTREN
Diisopropylidene mannofuranose (1) and dimethylphosphite react under base catalysis in an Abramow reaction with subsequent internal transesterification to yield the diasteromeric δ-phostones 2, which are also transformed into their crystalline tosylates 3.Surprisingly these compounds adapt a boat conformation, however, after change of the protecting groups a flat chair conformation (of 8 and 9) results.The δ-phostone formation (7) turned out to be the preferred reaction course even when the cyclic phosphite 6 is applied to react with 1.In basic medium the tosylate 3 does not undergo a ring contraction to a glycosyl phosphonate, however the 2-desoxy mannonic acid ester 10 is obtained: this is discussed and a mechanism proposed.Starting with the ribofuranose derivative 12 the corresponding δ-phostones 14 are prepared.In the reaction of the glucopyranose compound 16 a competition between the formation of ε-phostones 19 and the open-chain phosphonates 21 is observed.
Thiem, Joachim,Guenther, Michael
p. 67 - 80
(2007/10/02)

STEREOSELECTIVE SYNTHESIS OF 1,2-CIS-GLYCOFURANOSIDES USING GLYCOFURANOSYL FLUORIDES
1,2-cis-Ribofuranosides are stereoselectively synthesized in high yields by the reaction of β-ribofuranosyl fluoride and alkohols in the presence of stannous chloride and trityl perchlorate.Under similar condition, α-arabinofuranosyl fluoride reacts with
Mukaiyama, Teruaki,Hashimoto, Yukihiko,Shoda, Shin-ichiro
p. 935 - 938
(2007/10/02)

The Use of Grignard Reagents in the Synthesis of Carbohydrates. III. The One-way Anomerization of Methyl Glycofuranosides and the Opening of Their Furanose Rings
The anomerization of methyl glycofuranoside derivatives with methylmagnesium iodide or t-butylmagnesium bromide occurred in a one-way manner.For example, methyl 5-O-benzyl-β-D-ribofuranoside (3β) was converted into the corresponding α-anomer (3α) in a 95p
Kawana, Masajiro,Kuzuhara, Hiroyoshi,Emoto, Sakae
p. 1492 - 1504
(2007/10/02)