6160-50-5

Upstream product

• 132487-16-2 methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside 
• 452-51-7 D-2-deoxyribose 
• 922-65-6 divinylcarbinol 
• 533-67-5 2-Deoxy-D-ribose 
• 100-44-7 benzyl chloride 
• 221216-38-2 (2R,3R)-2-((benzyloxy)methyl)-3-vinyloxirane 
• 102490-00-6 (2S,3R)-1,2-epoxy-4-penten-3-ol 
• 100-39-0 benzyl bromide 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 120132-10-7 (2R,3S)-1,3-di-O-benzyl-4-pentene-1,2,3-triol 

Downstream Products

• 169221-19-6 2-(tert-butyldimethylsilyl)-5-(2-deoxy-3,5-di-O-benzyl-D-ribosyl)-N,N-dimethylimidazole-1-sulfonamide 
• 169139-35-9 2-(tert-butyldimethylsilyl)-5-(2-deoxy-3,5-di-O-benzyl-D-ribosyl)-N,N-dimethylimidazole-1-sulfonamide 
• 116444-15-6 (2R,3S)-1,3-O-dibenzyl-2-hydroxy-5-hexene 
• 503057-02-1 (2R,3S,5R)-3-benzyloxy-2-benzyloxymethyl-5-(trimethylsilylethynyl)tetrahydrofuran 
• 338800-85-4 (2R,3S,5R)-5-[2,2']Bipyridinyl-5-ylmethyl-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-ol 
• 340130-35-0 5-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylmethyl)-[2,2']bipyridinyl 
• 340130-37-2 (2R,3S,5S)-5-[2,2']Bipyridinyl-5-ylmethyl-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-ol 
• 170983-98-9 1β-cyano-3,5-di-O-benzyl-1,2-dideoxy-D-ribofuranose 
• 226232-74-2 1α-cyano-3,5-di-O-benzyl-1,2-dideoxy-D-ribofuranose 
• 226232-79-7 3,5-Di-O-benzyl-2-desoxy-β-D-ribofuranose-1-imidocarbonsaeuremethylester 
• 226232-77-5 3,5-Di-O-benzyl-2-desoxy-α-D-ribofuranose-1-imidocarbonsaeuremethylester 
• 226232-83-3 5-(3',5'-Di-O-benzyl-2'-desoxy-β-D-ribofuranosyl)-3,6-bis(trifluoromethyl)-1,2,4-triazin 
• 226232-81-1 5-(3',5'-Di-O-benzyl-2'-desoxy-α-D-ribofuranosyl)-3,6-bis(trifluoromethyl)-1,2,4-triazin 
• 232939-32-1 (3S,4S)-3,5-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-pentanal 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of C1-phosphonamidate analogues of 2-deoxy-d-ribose-1-phosphate

A novel series of phenoxy C1-phosphonamidate derivatives of 2-deoxy-d-ribose have been synthesised as stable analogues of 2-deoxy-α-d-ribose-1-phosphate. A number of synthetic routes were explored for the preparation of these targets. The successful approach involved the synthesis of a protected C1-phosphonate ester 17 via Michaelis-Arbuzov reaction, which was then hydrolysed and coupled with different amino acid esters using aldrithiol. Subsequent hydrogenolysis afforded the targets 2a-g, which were isolated as a mixture of diastereoisomers. The compounds were assayed for inhibition of thymidine phosphorylase (TP) and uridine phosphorylase (UP) and for antiviral and cytostatic activity.

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.

Secondary amine salt catalyzed controlled activation of 2-deoxy sugar lactols towards alpha-selective dehydrative glycosylation

A new organocatalytic glycosylation method exploiting the lactol functionality has been disclosed. The catalytic generation of glycosyl oxacarbenium ions from lactols under forcible conditions via weakly Br?nsted-acidic, readily available secondary amine salts affects the diastereoselective glycosylation of 2-deoxypyranoses and furanoses. This operationally simple iminium catalyzed activation of 2-deoxy hemi-acetals is a potential alternative to the existing cumbersome methods that need specialized handling. The mechanisms for this unique transformation and kinetic/thermodynamic effects have been discussed based on both experimental evidence and theoretical studies.

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.

Zeolite-Based Organic Synthesis (ZeoBOS) of Acortatarin A: First Total Synthesis Based on Native and Metal-Doped Zeolite-Catalyzed Steps

Similarly to polymer-supported assisted synthesis (PSAS), organic synthesis could be envisaged being performed by using zeolites, native or metal-doped, as heterogeneous catalysts. To illustrate this unprecedented Zeolite-Based Organic Synthesis (ZeoBOS),

Efficient synthesis of fluorescent alkynyl C-nucleosides via Sonogashira coupling for the preparation of DNA-based polyfluorophores

A facile and general procedure for the preparation of alkynyl C-nucleosides with varied fluorophores is presented. Sonogashira coupling was used as a key reaction to conjugate the dyes to an easily accessible ethynyl functionalized deoxyribose derivative.

A greener enantioselective synthesis of the antiviral agent North-methanocarbathymidine (N-MCT) from 2-deoxy-d-ribose

An enantioselective synthesis of suitably protected (1R,2S,4S,5S)-4-amino-1-(hydroxymethyl)bicyclo[3.1.0]hexan-2-ol, a key starting material for the synthesis of conformationally locked carbocyclic nucleosides, including the antiviral active North-methano

Studies on the generation of unnatural C-nucleosides with 1-alkynyl-2-deoxy-D-riboses

(Chemical Equation Presented) 1-Alkynyl-2-deoxy-D-riboses 7 and 8 were independently synthesized and subsequently used to generate several novel C-nucleosides.

Synthesis of new pyrrolidine c-nucleosides via Staudinger-aza-Wittig cyclization of γ-azido ketone

Novel N-acetyl C-aza-2-deoxy-D-ribonucleosides were synthesized from 2- deoxy-D-ribose via a consecutive procedure of the addition of ortho-lithiated pyrimidine salt, Staudinger-aza-Wittig ring cyclization, and reduction of cyclic imine.

Synthesis of novel Pyridine-, Pyrindine- and Isoquinoline-substituted α- and β-C-nucleosides of 2-deoxy-D-ribose

The novel imido esters of 2-deoxy-α- and -β-D-ribose 8 and 9 have been synthesized and successfully transformed to the protected 1,2,4-triazine-C-nucleosides 11 and 12 using an inverse type Diels-Alder reaction with the 1,2,4,5-tetrazine 10. The electron deficient diazadiene system of both C-nucleosides 11 and 12 proved to be highly reactive in a consecutive [4 + 2] cycloaddition with inverse electron demand towards several electron rich dienophiles yielding after successful deprotection the novel pyridine-, pyrindine- and isoquinoline-C-nucleosides 15, 18 and 21 of 2-deoxy-α-D-ribose and 23, 25 and 27 of 2-deoxy-β-D-ribose.