𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis and properties of 8,2′-N-cycloadenosines

✍ Scribed by Masakatsu Kaneko; Bunji Shimizu; Morio Ikehara

Publisher
Elsevier Science
Year
1971
Tongue
French
Weight
166 KB
Volume
12
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

In recent years the synthesis and properties of a variety of purine X-cyclonucleosides have been reported. 1) These cyclonucleosides have ox--g% or sulfur atom in their cycle-bond and a purine-8-cyclonucleoside has not 3een reported which has nitrogen atom in its cycle-bond. We reported herein the synthesis of the first purine 8-N-cyclonucleosides 2) starting from 8-bromo-2'-0-triisopropylbenzenesulfonyladenosine (8-Br-2'-TPS-adenosine). 3) When 8-Br-2' -TPS-adenosine was treated with excess liquid ammonia in pyridine at 90-100' for 34 hr, 8-amino-2' -TPS-adenosine (II) was obtained in the yield of 66%. (m.p. 167-9', IR. 1185 cm-l (sulfonyl), nmr. (6) 7.78 (lH, singlet, H-2), 6.62 (2H, singlet, 6-NH2), 6.40 (2H, singlet, 8-NH2). Cyclization of (II) with excess sodium acetate in dimethylformamide at refluxing temperature, gave compound (III) after purification of the reaction mixture through Dowex 1x4 (OH-) resin. (mp. 260'(decom.

📜 SIMILAR VOLUMES

ChemInform Abstract: Facile Synthesis of
ChemInform Abstract: Facile Synthesis of 8,2′-S-Cyclopurine Nucleoside.
✍ K. TEKENAKA; T. TSUJI; M. MURAOKA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 1 views

Facile Synthesis of 8,2'-S-Cyclopurine Nucleoside. -The title compound (VII), which may be biologically active, is prepared via the key intermediate (IV) by a shorter sequence compared to an earlier reported method.

8-Aza-7-deazaadenine N8- and N8-(β-D-2′-
8-Aza-7-deazaadenine N8- and N8-(β-D-2′-Deoxyribofuranosides): Building blocks for automated DNA synthesis and properties of oligodeoxyribonucleotides
✍ Frank Seela; Klaus Kaiser 📂 Article 📅 1988 🏛 John Wiley and Sons 🌐 German ⚖ 707 KB

A', is the symbol used for the 2'-deoxyadenosine moiety with the unusual Ns-instead of the usual fl-glycosidic linkage (purine numbering, see 1). The group Me,N-C(Me)= is represented by m,ma. The differences can also be attributed to the different attacking nucleophile (NH, us. OH-).

Synthesis, Reactions, and Properties of
Synthesis, Reactions, and Properties of 2,8-Didehydronoradamantane Derivatives
✍ Kata Mlinarić-Majerski; Goran Kragol 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 English ⚖ 244 KB 👁 1 views

Keywords: 2,8-Didehydronoradamantane derivatives / Cyclopropylcarbinyl / Rearrangements / Ring-opening reactions 2,8-Didehydronoradamantan-9-one (2) was readily prepared However, treatment of ketone 2 with PCl 5 proceeds through a concerted mechanism by cleavage of the C-1-C-2 bond in 2 by oxa-di-π-

Synthesis and photophysical properties o
Synthesis and photophysical properties of 8-arylbutadienyl 2′-deoxyguanosines
✍ Yoshio Saito; Makio Koda; Yuta Shinohara; Isao Saito 📂 Article 📅 2011 🏛 Elsevier Science 🌐 French ⚖ 525 KB

We have developed novel push-pull-type 8-arylbutadienyl 2 0 -deoxyguanosine derivatives, AB G (1a) and CB G (1b). These nucleosides exhibit strong solvent polarity dependent fluorescence emission at long wavelength (ca. 490-550 nm). These environmentally sensitive fluorescent deoxyguanosines are pow