101527-55-3

Basic information

• Product Name: 2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine
• Synonyms: 2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine
• CAS NO: 101527-55-3
• Molecular Weight: 548.617
• Mol File: 101527-55-3.mol

Chemical Properties

• CAS DataBase Reference: 2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine(101527-55-3)
• EPA Substance Registry System: 2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine(101527-55-3)

Safety Data

• Hazardous Substances Data: 101527-55-3(Hazardous Substances Data)

Upstream product

• 6554-10-5 5'-O-trityluridine 
• 101527-47-3 1-(2-hydroxy-1-{[1-hydroxy-3-(triphenylmethoxy)propan-2-yl]oxy}ethyl)pyrimidine-2,4(1H,3H)-dione 
• 101552-16-3 2',3'-di-O-mesyl-5'-O-trityl-2',3'-seco-uridine 

Downstream Products

• 101527-65-5 3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine 
• 101527-67-7 1-(R)-<6-(R)-trityloxymethyl-1,4-dioxan-2-yl>uracil 
• 263557-30-8 Methanesulfonic acid (R)-2-[(R)-1-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-phenylselanyl-ethoxy]-3-trityloxy-propyl ester 
• 263557-31-9 2'-deoxy-2'-phenylseleno-5'-O-trityl-2',3'-seco-uridine 
• 343263-69-4 3'-C-(Z)-(carbomethoxy)methylene-2',3'-dideoxy-2'-phenylseleno-5'-O-trityl-2',3'-seco-uridine 
• 263557-34-2 (E)-(R)-4-[(R)-1-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-phenylselanyl-ethoxy]-5-trityloxy-pent-2-enoic acid methyl ester 

Relevant articles and documents

Synthesis and anti-HIV activity of triazolo-fused, medium-sized cyclic nucleoside analogs prepared by an intramolecular huisgen 1,3-dipolar cycloaddition

Medium-sized cyclic nucleosides containing a fused triazole ring were synthesized via intramolecular Huisgen 1,3-dipolar cycloadditon reaction. 2′,3′-seco-Uridine was employed as the key intermediate for the introduction of azido and alkynyl moieties in the defined positions of the reaction precursors. The cycloaddition reactions were achieved in high yields by heating the precursor in refluxing toluene. The uracil base in these target compounds was successfully transformed to the corresponding cytosine. The synthesized compounds were evaluated in a MAGI assay for their anti-HIV activities, and in a H9 T lymphocytes assay for their cell toxicities. Copyright

Synthesis and reactions of some 3',4'-unsaturated 2',3'- secouridine analogues

2',3'-Dibromo-2',3'-dideoxy-5'-O-trityl-2',3'-secouridine (8) with sdKF gave the 3',4'-didehydro-2,2'-anhydro nucleoside 9, which was deprotected to 10. Hydrolysis of 9 gave 3',4'-didehydro-3'-deoxy-5'-O-trityl-2',3'- secouridine (11a). Similarly, compoun

Regioselective Transformations of 2',3'-Seconucleosides into Anhydro Structures and Chiral Crown Ethers

Intramolecular cyclisation of properly protected and activated derivatives of 2',3'-secouridine (= 1--ethyl>uracil; 1) provided access to the 2,2'-, 2,3'-, 2,5'-, 2',5'-, 3',5'-, and 2',3-anhydro-2',3'-secouridines 5, 16, 17, 26, 28 and 31, respectively (Schemes 1-3).Reaction of 2',5'-anhydro-3'-O-(methylsulfonyl)- (25) and 2',3'-anhydro-5'-O-(methylsulfonyl)-2',3'-secouridine (32) with CH2Cl2 in the presence of 1,8-diazabicycloundec-7-ene generated the N(3)-methylene-bridged bis-uridine structure 37 and 36, respectively (Scheme 3).Novel chiral 18-crown-6 ethers 40 and 44, containing a hydroxymethyl and a uracil-1-yl or adenin-9-yl as the pendant groups in a 1,3-cis relationship, were synthesized from 5'-O-(triphenylmethyl)-2',3'-secouridine (2) and 5'-O,N6-bis(triphenylmethyl)-2',3'-secoadenosine (41) on reaction with 3,6,9-trioxaundecane-1,11-diyl bis(4-toluenesulfonate) and detritylation of the thus obtained (triphenylmethoxy)methyl compound 39 and 43, respectively (Scheme 4).