𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A multigram, stereoselective synthesis of d-[13C5]ribose from d-[13C6]glucose and its conversion into [13C5]nucleosides

✍ Scribed by Luigi A. Agrofoglio; Jean-Claude Jacquinet; Gérard Lancelot

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
133 KB
Volume
38
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

The preparation of t3C-labeled ribonucleosides starting from D-[t3C~]glucose in 45% overall yield is described. The key of this short synthetic way is the dehomologation of di-O-isopropylidene hexofuranose 2 with periodic acid and NaBI-I4 that afforded stereoselectively the labeled ribofuranose derivative 3 in high yield.

📜 SIMILAR VOLUMES

Multiply 13C-substituted monosaccharides
Multiply 13C-substituted monosaccharides: synthesis of d-(1,5,6-13C3)glucose and d-(2,5,6-13C3)glucose
✍ Jian Wu; Anthony S. Serianni; Paul B. Bondo 📂 Article 📅 1992 🏛 Elsevier Science 🌐 English ⚖ 682 KB

D-(1,5,6-13C3)Glucose (7) has been synthesized by a six-step chemical method. D-(1,2-13C2)Mannose (1) was converted to methyl D-(1,2-13C2)mannopyranosides (2), and 2 was oxidized with Pt-C and O2 to give methyl D-(1,2-13C2)mannopyranuronides (3). After purification by anion-exchange chromatography,

Systematic synthesis of specifically 13C
Systematic synthesis of specifically 13C2H-labeled nucleosides from [ul-13C6]-d-glucose
✍ Akira (Mei) Ono; Toko Shiina; Akira Ono; Masatsune Kainosho 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 244 KB

A systematic approach, which combines previously reported reactions with appropriate modifications, was established for preparing a variety of selectively deuterated nucleosides from glucose• We have developed a systematic method of synthesizing specifically deuterated nucleosides from glucose.

Synthesis of [3-D3]-, [3-13C]-, and [1,2
Synthesis of [3-D3]-, [3-13C]-, and [1,2-13C2]Propynes and Their Use for the Synthesis of [5-D3-Methyl]-, [5-13C-Methyl]-, and [5,6-13C2-2,5-Cyclohexadienyl]ubiquinones 3
✍ Claude Boullais; Christelle Rannou; Emmanuel Réveillère; Charles Mioskowski 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 242 KB 👁 1 views

Three selectively labeled propynes were prepared either with deuterium or carbon-13 at position 3 and doubly labeled with carbon-13 at positions 1 and 2 by an alkylation reaction from the corresponding labeled or unlabeled monolithio acetylides and dimethylsulfates. Their lithiation with nBuLi gave